grepcent / static financial knowledge base

BENTLEY SYSTEMS INC (BSY)

CIK: 0001031308. SIC: 7372 Services-Prepackaged Software. Latest 10-K as of: 2026-02-26.

SIC breadcrumb: Services > Business Services > SIC 7372 Services-Prepackaged Software

SEC company page: https://www.sec.gov/edgar/browse/?CIK=1031308. Latest filing source: 0001031308-26-000007.

Informational only - descriptive public-record data, not investment advice.

Business

Read BSY's verbatim Item 1 Business section from its latest 10-K: Business.

Risk Factors

Read BSY's verbatim Item 1A Risk Factors from its latest 10-K: Risk Factors.

Selected Fundamentals

MetricValueUnitFYFiled
Revenue1,501,779,000USD20252026-02-26
Net income277,861,000USD20252026-02-26
Assets3,555,167,000USD20252026-02-26

Financials

Annual standardized facts from SEC companyfacts as of latest extracted filing date 2026-02-26. Source: https://data.sec.gov/api/xbrl/companyfacts/CIK0001031308.json. Derived margins, ratios, and free cash flow are computed from the extracted annual SEC facts.

Download these verified figures (annual + quarterly, with per-value filing provenance): JSON · CSV

Flow metrics use full-year FY periods from 10-K/10-K/A filings; balance-sheet metrics use FY-end instants. Free cash flow = operating cash flow - capital expenditures. Missing metrics are omitted rather than fabricated.

Metric201720182019202020212022202320242025
Revenue691,710,000736,654,000801,544,000965,046,0001,099,082,0001,228,413,0001,353,095,0001,501,779,000
Net income142,112,000103,096,000126,521,00093,192,000174,780,000326,787,000234,787,000277,861,000
Operating income121,391,000141,865,000150,150,00094,589,000208,612,000230,542,000302,150,000362,621,000
Gross profit560,386,000592,504,000634,389,000748,507,000862,069,000962,330,0001,095,328,0001,224,249,000
Diluted EPS0.490.350.420.300.551.000.720.85
Operating cash flow161,465,000170,773,000258,340,000288,024,000274,324,000416,696,000435,292,000538,464,000
Capital expenditures18,616,00016,639,00016,447,00017,539,00018,546,00025,002,00014,046,00018,255,000
Dividends paid20,059,00024,989,000422,646,00033,396,00034,493,00058,756,00072,115,00084,963,000
Share buybacks46,451,00024,166,0000.000.0028,250,0000.0064,359,000125,057,000
Assets994,599,0001,126,035,0002,659,243,0003,165,005,0003,319,850,0003,399,807,0003,555,167,000
Liabilities659,980,000784,436,0002,250,021,0002,591,551,0002,435,868,0002,358,687,0002,365,675,000
Stockholders' equity52,167,000147,431,000334,619,000341,599,000409,222,000883,278,0001,040,987,0001,189,413,000
Cash and cash equivalents121,101,000122,006,000329,337,00071,684,00068,412,00064,009,000123,278,000
Free cash flow142,849,000154,134,000241,893,000270,485,000255,778,000391,694,000421,246,000520,209,000

Ratios

ROE and ROA use period-end equity/assets. Liabilities / equity uses total liabilities divided by stockholders' equity. Current ratio uses current assets divided by current liabilities when both are reported.

Metric201720182019202020212022202320242025
Net margin20.55%14.00%15.78%9.66%15.90%26.60%17.35%18.50%
Operating margin17.55%19.26%18.73%9.80%18.98%18.77%22.33%24.15%
Return on equity96.39%30.81%37.04%22.77%37.00%22.55%23.36%
Return on assets10.37%11.24%3.50%5.52%9.84%6.91%7.82%
Liabilities / equity1.972.305.502.762.271.99
Current ratio0.900.731.040.660.550.540.56

Industry Peer Context

Each number-line places BSY against the min, median, and max of latest reported values among companies in the same SIC industry when at least three peers report that ratio.

Net margin peer context

BSY Net margin versus SIC peer range. Source: grepcent computed from latest SEC companyfacts ratios for SIC industry 7372; peer count 121.BSY Net margin versus SIC peer range. Source: grepcent computed from latest SEC companyfacts ratios for SIC industry 7372; peer count 121.121 SIC peersMin -134.9%Median 1.5%Max 39.9%BSY 18.5%

Operating margin peer context

BSY Operating margin versus SIC peer range. Source: grepcent computed from latest SEC companyfacts ratios for SIC industry 7372; peer count 120.BSY Operating margin versus SIC peer range. Source: grepcent computed from latest SEC companyfacts ratios for SIC industry 7372; peer count 120.120 SIC peersMin -108.2%Median 1.5%Max 48.8%BSY 24.1%

ROE peer context

BSY ROE versus SIC peer range. Source: grepcent computed from latest SEC companyfacts ratios for SIC industry 7372; peer count 112.BSY ROE versus SIC peer range. Source: grepcent computed from latest SEC companyfacts ratios for SIC industry 7372; peer count 112.112 SIC peersMin -270.0%Median 2.0%Max 135.2%BSY 23.4%

ROA peer context

BSY ROA versus SIC peer range. Source: grepcent computed from latest SEC companyfacts ratios for SIC industry 7372; peer count 124.BSY ROA versus SIC peer range. Source: grepcent computed from latest SEC companyfacts ratios for SIC industry 7372; peer count 124.124 SIC peersMin -77.9%Median 0.9%Max 150.6%BSY 7.8%

Financial Bridges

Waterfall figures reconcile reported SEC companyfacts components. Missing bridges are omitted when required components are not present for the same fiscal year.

Income statement bridge from reported figures

BSY FY2025 income statement bridge from reported figures.BSY FY2025 income statement bridge from reported figures.BSY income bridgeFY2025: revenue to net incomeSource: SEC companyfacts FY2025.Income statement bridgeReported amount$0.0B$1.0B$2.0B$1.5BRevenue-$277.5MCost$1.2BGross-$861.6MOpEx$362.6MOperating-$84.8MOther/tax$277.9MNet income

Figure provenance: SEC companyfacts FY 2025. Revenue: accession 0001031308-26-000007; concept RevenueFromContractWithCustomerExcludingAssessedTax; source concepts us-gaap:RevenueFromContractWithCustomerExcludingAssessedTax | Gross profit: accession 0001031308-26-000007; concept GrossProfit; source concepts us-gaap:GrossProfit | Operating income: accession 0001031308-26-000007; concept OperatingIncomeLoss; source concepts us-gaap:OperatingIncomeLoss | Net income: accession 0001031308-26-000007; concept NetIncomeLoss; source concepts us-gaap:NetIncomeLoss

Free cash flow = operating cash flow - capital expenditures

BSY FY2025 free cash flow bridge from reported figures.BSY FY2025 free cash flow bridge from reported figures.BSY free cash flow bridgeFY2025: operating cash flow less capital expendituresSource: SEC companyfacts FY2025.Free cash flow bridgeReported amount$0.0B$375.0M$750.0M$538.5MOperating cash flow-$18.3MCapex$520.2MFree cash flow

Figure provenance: SEC companyfacts FY 2025. Operating cash flow: accession 0001031308-26-000007; concept NetCashProvidedByUsedInOperatingActivities; source concepts us-gaap:NetCashProvidedByUsedInOperatingActivities | Capital expenditures: accession 0001031308-26-000007; concept PaymentsToAcquirePropertyPlantAndEquipment; source concepts us-gaap:PaymentsToAcquirePropertyPlantAndEquipment | Free cash flow: accession 0001031308-26-000007; concept NetCashProvidedByUsedInOperatingActivities - PaymentsToAcquirePropertyPlantAndEquipment; source concepts us-gaap:NetCashProvidedByUsedInOperatingActivities; us-gaap:PaymentsToAcquirePropertyPlantAndEquipment

Financial Charts

BSY revenue, last 5 periods. Source: SEC companyfacts FY2025.BSY revenue, last 5 periods. Source: SEC companyfacts FY2025.BSY RevenueLatest point: FY2025 = $1.5BSource: SEC companyfacts FY2025.Fiscal yearReported revenue$0.0B$1.0B$2.0BFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: RevenueFromContractWithCustomerExcludingAssessedTax. Source concepts: us-gaap:RevenueFromContractWithCustomerExcludingAssessedTax.

BSY net income, last 5 periods. Source: SEC companyfacts FY2025.BSY net income, last 5 periods. Source: SEC companyfacts FY2025.BSY Net incomeLatest point: FY2025 = $277.9MSource: SEC companyfacts FY2025.Fiscal yearNet income$0.0B$250.0M$500.0MFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: NetIncomeLoss. Source concepts: us-gaap:NetIncomeLoss.

BSY operating income, last 5 periods. Source: SEC companyfacts FY2025.BSY operating income, last 5 periods. Source: SEC companyfacts FY2025.BSY Operating incomeLatest point: FY2025 = $362.6MSource: SEC companyfacts FY2025.Fiscal yearOperating income$0.0B$250.0M$500.0MFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: OperatingIncomeLoss. Source concepts: us-gaap:OperatingIncomeLoss.

BSY gross profit, last 5 periods. Source: SEC companyfacts FY2025.BSY gross profit, last 5 periods. Source: SEC companyfacts FY2025.BSY Gross profitLatest point: FY2025 = $1.2BSource: SEC companyfacts FY2025.Fiscal yearGross profit$0.0B$1.0B$2.0BFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: GrossProfit. Source concepts: us-gaap:GrossProfit.

BSY diluted eps, last 5 periods. Source: SEC companyfacts FY2025.BSY diluted eps, last 5 periods. Source: SEC companyfacts FY2025.BSY Diluted EPSLatest point: FY2025 = $0.85/shareSource: SEC companyfacts FY2025.Fiscal yearDiluted EPS (USD/share)$0.00/share$0.75/share$1.50/shareFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: EarningsPerShareDiluted. Source concepts: us-gaap:EarningsPerShareDiluted.

BSY operating cash flow, last 5 periods. Source: SEC companyfacts FY2025.BSY operating cash flow, last 5 periods. Source: SEC companyfacts FY2025.BSY Operating cash flowLatest point: FY2025 = $538.5MSource: SEC companyfacts FY2025.Fiscal yearOperating cash flow$0.0B$375.0M$750.0MFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: NetCashProvidedByUsedInOperatingActivities. Source concepts: us-gaap:NetCashProvidedByUsedInOperatingActivities.

BSY capital expenditures, last 5 periods. Source: SEC companyfacts FY2025.BSY capital expenditures, last 5 periods. Source: SEC companyfacts FY2025.BSY Capital expendituresLatest point: FY2025 = $18.3MSource: SEC companyfacts FY2025.Fiscal yearCapital expenditures$0.0B$125.0M$250.0MFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: PaymentsToAcquirePropertyPlantAndEquipment. Source concepts: us-gaap:PaymentsToAcquirePropertyPlantAndEquipment.

BSY dividends paid, last 5 periods. Source: SEC companyfacts FY2025.BSY dividends paid, last 5 periods. Source: SEC companyfacts FY2025.BSY Dividends paidLatest point: FY2025 = $85.0MSource: SEC companyfacts FY2025.Fiscal yearDividends paid$0.0B$125.0M$250.0MFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: PaymentsOfDividends. Source concepts: us-gaap:PaymentsOfDividends.

BSY share buybacks, last 5 periods. Source: SEC companyfacts FY2025.BSY share buybacks, last 5 periods. Source: SEC companyfacts FY2025.BSY Share buybacksLatest point: FY2025 = $125.1MSource: SEC companyfacts FY2025.Fiscal yearShare buybacks$0.0B$125.0M$250.0MFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: PaymentsForRepurchaseOfCommonStock. Source concepts: us-gaap:PaymentsForRepurchaseOfCommonStock.

BSY assets, last 5 periods. Source: SEC companyfacts FY2025.BSY assets, last 5 periods. Source: SEC companyfacts FY2025.BSY AssetsLatest point: FY2025 = $3.6BSource: SEC companyfacts FY2025.Fiscal yearAssets$0.0B$2.0B$4.0BFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: Assets. Source concepts: us-gaap:Assets.

BSY liabilities, last 5 periods. Source: SEC companyfacts FY2025.BSY liabilities, last 5 periods. Source: SEC companyfacts FY2025.BSY LiabilitiesLatest point: FY2025 = $2.4BSource: SEC companyfacts FY2025.Fiscal yearLiabilities$0.0B$2.0B$4.0BFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: Liabilities. Source concepts: us-gaap:Liabilities.

BSY stockholders' equity, last 5 periods. Source: SEC companyfacts FY2025.BSY stockholders' equity, last 5 periods. Source: SEC companyfacts FY2025.BSY Stockholders' equityLatest point: FY2025 = $1.2BSource: SEC companyfacts FY2025.Fiscal yearStockholders' equity$0.0B$1.0B$2.0BFY2020FY2021FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: StockholdersEquity. Source concepts: us-gaap:StockholdersEquity.

BSY cash and cash equivalents, last 5 periods. Source: SEC companyfacts FY2025.BSY cash and cash equivalents, last 5 periods. Source: SEC companyfacts FY2025.BSY Cash and cash equivalentsLatest point: FY2025 = $123.3MSource: SEC companyfacts FY2025.Fiscal yearCash and cash equivalents$0.0B$250.0M$500.0MFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: CashAndCashEquivalentsAtCarryingValue. Source concepts: us-gaap:CashAndCashEquivalentsAtCarryingValue.

BSY free cash flow, last 5 periods. Source: SEC companyfacts FY2025.BSY free cash flow, last 5 periods. Source: SEC companyfacts FY2025.BSY Free cash flowLatest point: FY2025 = $520.2MSource: SEC companyfacts FY2025.Fiscal yearFree cash flow$0.0B$375.0M$750.0MFY2021FY2022FY2023FY2024FY2025

Figure provenance: SEC companyfacts. Latest point: FY 2025 ended 2025-12-31; accession 0001031308-26-000007; filed 2026-02-26. Concept: NetCashProvidedByUsedInOperatingActivities - PaymentsToAcquirePropertyPlantAndEquipment. Source concepts: us-gaap:NetCashProvidedByUsedInOperatingActivities; us-gaap:PaymentsToAcquirePropertyPlantAndEquipment.

Quarterly

Quarterly standardized facts from SEC companyfacts as of latest extracted filing date 2026-05-07. Source: https://data.sec.gov/api/xbrl/companyfacts/CIK0001031308.json.

Flow metrics use discrete quarter-length periods from 10-Q/10-Q/A filings. Q4 revenue and net income are derived only when annual FY and nine-month YTD facts exist for the same fiscal year; derived Q4 values are labeled. EPS Q4 is not derived.

QuarterEnd DateRevenueNet IncomeDiluted EPSMethod
2022-Q22022-06-300.17reported discrete quarter
2022-Q32022-09-300.12reported discrete quarter
2023-Q12023-03-310.14reported discrete quarter
2023-Q22023-06-30296,749,00048,685,0000.15reported discrete quarter
2023-Q32023-09-30306,612,00053,027,0000.16reported discrete quarter
2023-Q42023-12-31310,641,000179,585,000derived Q4 = FY annual - nine-month YTD
2024-Q12024-03-31337,763,00070,310,0000.22reported discrete quarter
2024-Q22024-06-30330,337,00072,046,0000.22reported discrete quarter
2024-Q32024-09-30335,173,00042,338,0000.13reported discrete quarter
2024-Q42024-12-31349,822,00050,093,000derived Q4 = FY annual - nine-month YTD
2025-Q12025-03-31370,542,00091,368,0000.28reported discrete quarter
2025-Q22025-06-30364,106,00070,482,0000.22reported discrete quarter
2025-Q32025-09-30375,549,00057,373,0000.18reported discrete quarter
2025-Q42025-12-31391,582,00058,638,000derived Q4 = FY annual - nine-month YTD
2026-Q12026-03-31424,181,00095,386,0000.30reported discrete quarter

Quarterly Charts

BSY quarterly revenue, last 12 periods. Source: SEC companyfacts 2026-Q1.BSY quarterly revenue, last 12 periods. Source: SEC companyfacts 2026-Q1.BSY Quarterly RevenueLatest point: 2026-Q1 = $424.2MSource: SEC companyfacts 2026-Q1.Fiscal quarterQuarterly Revenue$0.0B$250.0M$500.0M2023-Q22023-Q32023-Q42024-Q12024-Q22024-Q32024-Q42025-Q12025-Q22025-Q32025-Q42026-Q1

Figure provenance: SEC companyfacts. Latest point: FY 2026 ended 2026-03-31; accession 0001031308-26-000017; filed 2026-05-07. Concept: RevenueFromContractWithCustomerExcludingAssessedTax. Source concepts: us-gaap:RevenueFromContractWithCustomerExcludingAssessedTax.

BSY quarterly net income, last 12 periods. Source: SEC companyfacts 2026-Q1.BSY quarterly net income, last 12 periods. Source: SEC companyfacts 2026-Q1.BSY Quarterly Net incomeLatest point: 2026-Q1 = $95.4MSource: SEC companyfacts 2026-Q1.Fiscal quarterQuarterly Net income$0.0B$125.0M$250.0M2023-Q22023-Q32023-Q42024-Q12024-Q22024-Q32024-Q42025-Q12025-Q22025-Q32025-Q42026-Q1

Figure provenance: SEC companyfacts. Latest point: FY 2026 ended 2026-03-31; accession 0001031308-26-000017; filed 2026-05-07. Concept: NetIncomeLoss. Source concepts: us-gaap:NetIncomeLoss.

BSY quarterly diluted eps, last 12 periods. Source: SEC companyfacts 2026-Q1.BSY quarterly diluted eps, last 12 periods. Source: SEC companyfacts 2026-Q1.BSY Quarterly Diluted EPSLatest point: 2026-Q1 = $0.30/shareSource: SEC companyfacts 2026-Q1.Fiscal quarterQuarterly Diluted EPS (USD/share)$0.00/share$0.25/share$0.50/share2022-Q22022-Q32023-Q12023-Q22023-Q32024-Q12024-Q22024-Q32025-Q12025-Q22025-Q32026-Q1

Figure provenance: SEC companyfacts. Latest point: FY 2026 ended 2026-03-31; accession 0001031308-26-000017; filed 2026-05-07. Concept: EarningsPerShareDiluted. Source concepts: us-gaap:EarningsPerShareDiluted.

Macro Cross-References

Latest quarter (10-Q)

Latest 10-Q source: 0001031308-26-000017.

Extracted structurally from real Item 2 body heading to real Item 3/4 boundary. Confidence: high. Filing date: 2026-05-07. Report date: 2026-03-31.

Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations

The following discussion should be read in conjunction with our unaudited consolidated financial statements and notes thereto appearing in Part I, Item 1 of this Quarterly Report on Form 10‑Q and with our audited consolidated financial statements and notes thereto included in our 2025 Annual Report on Form 10‑K.

All amounts presented in this Management’s Discussion and Analysis of Financial Condition and Results of Operations, except share and per share amounts, are presented in thousands. Additionally, many of the amounts and percentages have been rounded for convenience of presentation. Minor differences in totals and percentage calculations may exist due to rounding.

Overview:

Bentley Systems is the infrastructure engineering software company. Our purpose is to advance the world’s infrastructure for better quality of life. Our mission is to reshape how infrastructure systems and critical resources are delivered and optimized. We manage our business globally within one reportable segment, the development and marketing of computer software and related services, which is consistent with how our CODM reviews and manages our business.

Executive Summary:

•Total revenues were $424,181 for the three months ended March 31, 2026, up 14.5% or 11.9% on a constant currency basis(1) compared to the three months ended March 31, 2025;

•Subscriptions revenues were $392,484 for the three months ended March 31, 2026, up 14.7% or 12.2% on a constant currency basis(1) compared to the three months ended March 31, 2025;

•Annualized recurring revenues (“ARR”)(2) was $1,494,511 as of March 31, 2026, compared to $1,319,256 as of March 31, 2025; Constant currency(1) ARR growth rate(2) was 11.5%;

•Last twelve-month recurring revenues dollar-based net retention rate(2) was 109% as of March 31, 2026, compared to 110% as of March 31, 2025;

•Operating income was $126,260 for the three months ended March 31, 2026, compared to $115,184 for the three months ended March 31, 2025;

•AOI less Operating SBC(1) was $140,923 for the three months ended March 31, 2026, compared to $128,308 for the three months ended March 31, 2025; and

•Cash flows from operating activities were $193,408 for the three months ended March 31, 2026, compared to $219,415 for the three months ended March 31, 2025.

(1)Constant currency and AOI less Operating SBC are non‑GAAP financial measures. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our definitions and our uses of constant currency and AOI less Operating SBC.

(2)Refer to the “Key Business Metrics” section for additional information, including our definitions and our uses of ARR, ARR growth rate, and recurring revenues dollar-based net retention rate.

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Results of Operations:

Our results of operations have been, and in the future will be, affected by changes in foreign currency exchange rates. Other than the natural hedge attributable to matching revenues and expenses in the same currencies, we do not currently hedge foreign currency exposure.

We identify the effects of foreign currency on our operations and present constant currency growth rates and fluctuations because we believe exchange rates are an important factor in understanding period‑over‑period comparisons and enhance the understanding of our results and evaluation of our performance. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our definition and our use of constant currency.

Revenues

Consolidated Revenues

Change
Three Months EndedConstant
March 31,Currency
20262025%%(1)
Subscriptions$392,484$342,31814.7%12.2%
Perpetual licenses9,05710,792(16.1%)(18.0%)
Subscriptions and licenses401,541353,11013.7%11.3%
Services22,64017,43229.9%25.8%
Total revenues$424,181$370,54214.5%11.9%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

The increase in total revenues for the three months ended March 31, 2026 was primarily driven by an increase in subscriptions revenues, and to a lesser extent, an increase in services revenues, partially offset by a decrease in perpetual licenses revenues. Our business performance includes the impact from programmatic acquisitions, which generally are immaterial, individually and in the aggregate.

Subscriptions. For the three months ended March 31, 2026, subscriptions revenues increased $50,166 ($41,734 on a constant currency basis) primarily driven by expansion from accounts with revenues in the same period in the prior year (“existing accounts”), and growth of 3% attributable to new accounts, most notably small- and medium-sized accounts. Increases in subscriptions revenues for the three months ended March 31, 2026 were led by Bentley Open Applications and Seequent applications, and to a lesser extent, Bentley Infrastructure Cloud.

Perpetual licenses. For the three months ended March 31, 2026, perpetual licenses revenues decreased $1,735 ($1,946 on a constant currency basis).

Services. For the three months ended March 31, 2026, services revenues increased $5,208 ($4,496 on a constant currency basis) primarily due to strength in Maximo-related work within our digital integrator.

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Revenues by Geographic Region

Revenue from external customers is attributed to individual countries based upon the location of the customer.

Change
Three Months EndedConstant
March 31,Currency
20262025%%(1)
Americas$225,634$198,97513.4%12.7%
EMEA126,241107,00518.0%11.9%
APAC72,30664,56212.0%9.6%
Total revenues$424,181$370,54214.5%11.9%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

Americas. For the three months ended March 31, 2026, revenues from the Americas increased $26,659 ($25,323 on a constant currency basis) primarily due to expansion of our subscriptions revenues from existing accounts in the U.S., increases in our subscription revenues from new accounts, as well as an increase in services revenues.

EMEA. For the three months ended March 31, 2026, revenues from EMEA increased $19,236 ($12,787 on a constant currency basis) primarily due to expansion of our subscriptions revenues from existing accounts, and to a lesser extent, increases in our subscriptions revenues from new accounts, and an increase in services revenues.

APAC. For the three months ended March 31, 2026, revenues from APAC increased $7,744 ($6,174 on a constant currency basis) primarily due to expansion of our subscriptions revenues from existing accounts in India and Australia, as well as increases in our subscriptions revenues from new accounts, partially offset by a decline in perpetual licenses revenues.

Cost of Revenues and Operating Expense (Income)

Cost of Revenues

Change
Three Months EndedConstant
March 31,Currency
20262025%%(1)
Cost of subscriptions and licenses$53,098$46,49814.2%11.9%
Cost of services20,67619,1617.9%3.1%
Total cost of revenues$73,774$65,65912.4%9.3%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

Cost of subscriptions and licenses. For the three months ended March 31, 2026, on a constant currency basis, cost of subscriptions and licenses expenses increased primarily due to an increase in cloud-related costs of $5,683.

Cost of services. For the three months ended March 31, 2026, on a constant currency basis, cost of services expenses increased primarily due to an increase in headcount‑related costs of $668, mainly due to an increase in third‑party personnel costs, partially offset by decreases in headcount, and annual and other compensation costs.

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Operating Expense (Income)

Change
Three Months EndedConstant
March 31,Currency
20262025%%(1)
Research and development$83,005$72,45014.6%10.8%
Selling and marketing75,27263,05919.4%15.0%
General and administrative58,50947,22823.9%21.1%
Deferred compensation plan(1,074)(1,246)(13.8%)(13.8%)
Amortization of purchased intangibles8,4358,2082.8%2.0%
Total operating expenses$224,147$189,69918.2%14.5%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

Research and development. For the three months ended March 31, 2026, on a constant currency basis, research and development expenses increased primarily due to an increase in headcount‑related costs of $6,436, mainly due to increases in headcount, and annual and other compensation costs, and to a lesser extent, higher acquisition‑related retention incentives.

Selling and marketing. For the three months ended March 31, 2026, on a constant currency basis, selling and marketing expenses increased primarily due to an increase in headcount‑related costs of $6,184, mainly due to increases in annual and other compensation costs, and an increase in promotional costs of $2,428.

General and administrative. For the three months ended March 31, 2026, on a constant currency basis, general and administrative expenses increased primarily due to an increase in headcount‑related costs of $7,135, mainly due to increases in headcount, and annual and other compensation costs, and an increase in third-party personnel costs. Additionally, during the three months ended March 31, 2026, general and administrative expenses further increased due to lower capitalizable costs associated with our internal-use software implementation as compared to the same period in the prior year.

Starting in 2026, we expect general and administrative expenses to include amortization of internal-use software implementation costs, which represents amortization of deferred costs primarily related to the implementation of our new enterprise-wide administrative and business management platforms which are planned to complete going live in 2026.

Deferred compensation plan. For the three months ended March 31, 2026 and 2025, deferred compensation plan income was attributable to the marked to market impact on deferred compensation plan liability balances period over period.

Amortization of purchased intangibles. For the three

[Excerpt truncated for page length; source filing is linked above.]

Latest 10-K MD&A

Extracted structurally from real Item 7 body heading to real Item 7A/8 boundary. Confidence: high. Filing date: 2026-02-26. Report date: 2025-12-31.

Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations

The following discussion should be read in conjunction with our audited consolidated financial statements and notes thereto included in Part II, Item 8 of this Annual Report on Form 10‑K. In addition to historical information, this discussion contains forward‑looking statements that involve risks, uncertainties, and assumptions that could cause actual results to differ materially from management’s expectations. Factors that could cause such differences are set forth in Part I, Item 1A. Risk Factors of this Annual Report on Form 10‑K. Refer to Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations in our 2024 Annual Report on Form 10‑K for management’s discussion and analysis of financial condition and results of operations for the year ended December 31, 2024 compared to the year ended December 31, 2023.

All amounts presented in this Management’s Discussion and Analysis of Financial Condition and Results of Operations, except share and per share amounts, are presented in thousands. Additionally, many of the amounts and percentages have been rounded for convenience of presentation. Minor differences in totals and percentage calculations may exist due to rounding.

Overview:

Bentley Systems is the infrastructure engineering software company. Our purpose is to advance the world’s infrastructure for better quality of life. Our mission is to reshape how infrastructure systems and critical resources are delivered and optimized. We manage our business globally within one reportable segment, the development and marketing of computer software and related services, which is consistent with how our chief operating decision maker (“CODM”) reviews and manages our business.

Executive Summary:

•Total revenues were $1,501,779 for the year ended December 31, 2025, up 11.0% or 10.1% on a constant currency basis(1) compared to the prior year;

•Subscriptions revenues were $1,376,696 for the year ended December 31, 2025, up 12.5% or 11.7% on a constant currency basis(1) compared to the prior year;

•ARR(2) was $1,462,145 as of December 31, 2025, compared to $1,283,256 as of December 31, 2024; Constant currency(1) ARR growth rate(2) was 11.5%;

•Last twelve-month recurring revenues dollar-based net retention rate(2) was 109% as of December 31, 2025, compared to 110% as of December 31, 2024;

•Operating income was $362,621 for the year ended December 31, 2025, compared to $302,150 for the prior year;

•Adjusted operating income less stock-based compensation expense (“AOI less SBC”) (previously titled Adjusted operating income inclusive of stock-based compensation expense (“Adjusted OI w/SBC”))(1) was $429,917 for the year ended December 31, 2025, compared to $372,222 for the prior year; and

•Cash flows from operating activities were $538,464 for the year ended December 31, 2025, compared to $435,292 for the prior year.

(1)Constant currency and AOI less SBC are non‑GAAP financial measures. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our definitions and our uses of constant currency and AOI less SBC.

(2)Refer to the “Key Business Metrics” section for additional information, including our definitions and our uses of ARR, ARR growth rate, and recurring revenues dollar-based net retention rate.

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Results of Operations:

Our results of operations have been, and in the future will be, affected by changes in foreign currency exchange rates. For the years ended December 31, 2025, 2024, and 2023, approximately 33%, 34%, and 35%, respectively, of our total revenues and 45%, 42%, and 45%, respectively, of our total operating expenses were denominated in a currency other than the U.S. dollar including most significantly: euros, British pounds, Canadian dollars, Australian dollars, Chinese yuan renminbi, and New Zealand dollars. Other than the natural hedge attributable to matching revenues and expenses in the same currencies, we do not currently hedge foreign currency exposure. Additionally, because we have operations in, and derive revenue from, geographies around the world, we will continue to monitor the impact of tariffs and other trade policies on our business and the businesses of our accounts, as well as on our financial condition, results of operations, and/or cash flows.

We identify the effects of foreign currency on our operations and present constant currency growth rates and fluctuations because we believe exchange rates are an important factor in understanding period‑over‑period comparisons and enhance the understanding of our results and evaluation of our performance. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our definition and our use of constant currency.

Revenues

We generate revenues from subscriptions, perpetual licenses, and services. Our total revenues are diversified by account type, size, and geographic region. The majority of our revenue growth, excluding the impact from acquisitions, is driven by additional subscriptions revenues from existing accounts using the same products. To a lesser extent, our revenue growth is attributable to subscriptions revenues from new accounts and subscriptions revenues from existing accounts using new products. We believe that we have a loyal account base, with over 70% of our total revenues for the years ended December 31, 2025, 2024, and 2023 generated from organizations that have been our accounts for over ten years.

In addition to our results of operations discussed below, the following is supplemental data of our revenues:

Year Ended December 31,
(as a percentage of total revenues)202520242023
Revenues from:
Direct sales channels94%93%92%
Indirect channel partners6%7%8%
Revenues from:
Subscriptions92%90%88%
Recurring services1%1%1%
Total recurring revenues93%91%89%
Perpetual licenses and other services7%9%11%
Largest account represents no more than2%2%2%

The volume, mix, and duration of contract types starting or renewing in any given period may have a material impact on revenue in the period, and as a result can impact the comparability of reported revenue period-over-period. Our subscriptions, perpetual licenses, and services offerings are recognized pursuant to applicable GAAP guidance. See Note 3 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our revenues. We believe that subscription revenues will continue to comprise a majority of our total revenues.

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Consolidated Revenues

% Change% Change
2024 to 20252023 to 2024
ConstantConstant
Year Ended December 31,CurrencyCurrency
202520242023%%(1)%%(1)
Subscriptions$1,376,696$1,223,362$1,080,30712.5%11.7%13.2%13.4%
Perpetual licenses46,18045,96146,0380.5%0.1%(0.2%)0.5%
Subscriptions and licenses1,422,8761,269,3231,126,34512.1%11.2%12.7%12.9%
Services78,90383,772102,068(5.8%)(6.6%)(17.9%)(18.2%)
Total revenues$1,501,779$1,353,095$1,228,41311.0%10.1%10.1%10.3%

(1)Constant currency is a non‑GAAP financial measure. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

The increase in total revenues for the year ended December 31, 2025 was primarily driven by an increase in subscriptions revenues, partially offset by a decrease in services revenues.

Subscriptions. For the year ended December 31, 2025, the increase in subscriptions revenues was driven by improvements in our business performance of $153,334 ($142,592 on a constant currency basis). Our business performance includes the impact from programmatic acquisitions, which generally are immaterial, individually and in the aggregate.

For the year ended December 31, 2025, the improvements in business performance were primarily driven by expansion from accounts with revenues in the prior period (“existing accounts”), and growth of 2.5% attributable to new accounts, most notably small- and medium-sized accounts. Improvements in business performance for the year ended December 31, 2025 were led by Bentley Open Applications, followed by Seequent applications, and Bentley Infrastructure Cloud.

Perpetual licenses. For the year ended December 31, 2025, perpetual licenses revenues were flat compared to the prior year.

Services. For the year ended December 31, 2025, the decrease in services revenues was driven by a decline in our business performance of $4,869 ($5,548 on a constant currency basis), primarily due to the winding down of a large services project in the beginning of 2025.

Revenues by Geographic Region

Revenue from external customers is attributed to individual countries based upon the location of the customer.

% Change% Change
2024 to 20252023 to 2024
ConstantConstant
Year Ended December 31,CurrencyCurrency
202520242023%%(1)%%(1)
Americas$790,495$717,002$650,92610.3%10.4%10.2%10.5%
EMEA436,828388,384353,55012.5%9.2%9.9%9.1%
APAC274,456247,709223,93710.8%10.7%10.6%11.8%
Total revenues$1,501,779$1,353,095$1,228,41311.0%10.1%10.1%10.3%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

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Americas. For the year ended December 31, 2025, the increase in revenues from the Americas was primarily driven by improvements in our business performance of $73,493 ($74,816 on a constant currency basis).

The improvements in business performance for the year ended December 31, 2025 were primarily due to expansion of our subscriptions revenues from existing accounts in the U.S., as well as increases in our subscriptions revenues from new accounts.

EMEA. For the year ended December 31, 2025, the increase in revenues from EMEA was primarily driven by improvements in our business performance of $48,444 ($35,754 on a constant currency basis).

The improvements in business performance for the year ended December 31, 2025 were primarily due to expansion of our subscriptions revenues from existing accounts in the United Kingdom (“U.K.”) and the Middle East, as well as increases in our subscriptions revenues from new accounts, partially offset by a decline in services revenues.

APAC. For the year ended December 31, 2025, the increase in revenues from APAC was primarily driven by improvements in our business performance of $26,747 ($26,524 on a constant currency basis).

The improvements in business performance for the year ended December 31, 2025 were primarily due to expansion of our subscriptions revenues from existing accounts in Australia and India, as well as increases in our subscriptions revenues from new accounts.

Additionally, for the year ended December 31, 2025, our revenues in China were essentially flat. Our perpetual licenses revenues in China increased primarily due to expansion from new accounts, partially offset by a decline from existing accounts. Our subscriptions revenues in China decreased primarily due to a decline from existing accounts, partially offset by an increase from new accounts.

The future results in China remain uncertain as a result of continued geopolitical challenges, the obstacles there to cloud‑deployed software, and the financial timing impact of the preference there for license sales, rather than subscriptions.

Cost of Revenues and Operating Expenses

Headcount-Related Costs

For the years ended December 31, 2025, 2024, and 2023, approximately 80% of our aggregate cost of revenues, research and development, selling and marketing, and general and administrative expenses were represented by what we refer to herein as “headcount‑related” costs. These costs primarily include salaries, benefits, bonuses, stock‑based compensation expense, employment taxes, travel, training, and realignment and optimization of our colleagues, and third‑party personnel expenses and related overhead. Our headcount‑related costs are variable in nature. We actively manage these costs to align to our trending run rate of revenue performance, with the objective of enhancing visibility and predictability of resulting operating profit margins.

During the fourth quarter of 2023, we approved a strategic realignment program to better serve our accounts and to better align resources with the strategy of the business, including reinvestment in go-to-market functions, as well as in AI in product development (the “2023 Program”). The realignment program resulted in realignment costs of $847 and $12,579 for the years ended December 31, 2024 and 2023, respectively, which represent termination benefits for colleagues whose roles were impacted (less than five percent of total headcount). See Note 21 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information. The 2023 Program activities, including payments of termination benefits, were completed as of December 31, 2024.

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Cost of Revenues

% Change% Change
2024 to 20252023 to 2024
ConstantConstant
Year Ended December 31,CurrencyCurrency
202520242023%%(1)%%(1)
Cost of subscriptions and licenses$201,405$173,340$169,40616.2%15.9%2.3%2.4%
Cost of services76,12584,42796,677(9.8%)(10.8%)(12.7%)(12.8%)
Total cost of revenues$277,530$257,767$266,0837.7%7.1%(3.1%)(3.1%)

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

Cost of subscriptions and licenses. Cost of subscriptions and licenses expenses primarily include headcount‑related costs, as well as cloud‑related costs incurred for servicing our accounts using cloud provisioned offerings and our license administration platform. Cost of subscriptions and licenses expenses also include channel partner compensation for providing sales coverage to users, depreciation of property and equipment, amortization of capitalized software costs associated with servicing software subscriptions and our Accelerated Commercial Development Program (“ACDP”), and amortization of intangible assets associated with acquired software and technology.

For the year ended December 31, 2025, on a constant currency basis, cost of subscriptions and licenses expenses increased primarily due to an increase in headcount‑related costs of $15,149, mainly due to an increase in annual and other compensation costs, and an increase in cloud-related costs of $10,007.

Cost of services. Cost of services expenses primarily include headcount‑related costs, as well as depreciation of property and equipment, and amortization of capitalized software costs used for providing training, implementation, configuration, and customization services to accounts.

For the year ended December 31, 2025, on a constant currency basis, cost of services expenses decreased primarily due to a decrease in headcount‑related costs of $6,718, mainly due to a reduction in third‑party personnel costs, and to a lesser extent, lower annual and other compensation costs.

Operating Expenses

% Change% Change
2024 to 20252023 to 2024
ConstantConstant
Year Ended December 31,CurrencyCurrency
202520242023%%(1)%%(1)
Research and development$307,576$281,247$274,6199.4%9.1%2.4%2.7%
Selling and marketing289,543255,177224,33613.5%12.8%13.7%14.1%
General and administrative217,332210,374180,7383.3%2.9%16.4%16.5%
Deferred compensation plan14,40912,38213,58016.4%16.4%(8.8%)(8.8%)
Amortization of purchased intangibles32,76833,99838,515(3.6%)(3.8%)(11.7%)(11.8%)
Total operating expenses$861,628$793,178$731,7888.6%8.2%8.4%8.6%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

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Research and development. Research and development expenses primarily consist of headcount‑related costs, including costs to develop software products or the software component of products to be sold, leased, or marketed to external accounts, before technological feasibility is reached, which is generally shortly before the release of such products. Our research and development roadmap balances technology advances and new offerings with continuous enhancements to existing offerings. Our allocation of research and development resources is based on a cost‑benefit analysis of acquiring available technology in the marketplace versus developing our own software. We anticipate that we will continue to make substantial investments in research and development because we believe the infrastructure engineering software market presents compelling opportunities for the application of new technologies that advance our current offerings.

For the year ended December 31, 2025, on a constant currency basis, research and development expenses increased primarily due to an increase in headcount‑related costs of $25,665, mainly due to increases in headcount, and annual and other compensation costs, and to a lesser extent, higher colleague separation costs. Headcount‑related costs for the year ended December 31, 2024 were lower due to run‑rate savings as a result of the 2023 Program.

Selling and marketing. Selling and marketing expenses primarily include headcount‑related costs, as well as the expense of online marketing, product marketing and other brand‑building activities, such as advertising, trade shows, and expositions, and various sales and promotional programs. We anticipate that we will continue to make strategic investments in our global business systems and methods to enhance major account sales activities and to support our worldwide sales and marketing strategies, and the business in general.

For the year ended December 31, 2025, on a constant currency basis, selling and marketing expenses increased primarily due to an increase in headcount‑related costs of $24,174, mainly due to increases in headcount, and annual and other compensation costs, and an increase in promotional costs of $6,216. Headcount‑related costs for the year ended December 31, 2024 were lower due to run‑rate savings as a result of the 2023 Program.

General and administrative. General and administrative expenses primarily include headcount‑related costs for our finance, human resources, and legal functions, as well as professional fees for legal and accounting services. General and administrative expenses also include acquisition costs, which consist of costs related to legal, accounting, valuation, insurance, and other consulting and transaction fees. Acquisition costs may drive fluctuations in general and administrative expenses depending on the timing of business combinations.

Starting in 2026, we expect general and administrative expenses to include amortization of internal-use software implementation costs, which represents amortization of deferred costs primarily related to the implementation of our new enterprise-wide administrative and business management platforms which are planned to complete going live in 2026.

For the year ended December 31, 2025, on a constant currency basis, general and administrative expenses increased primarily due to an increase in headcount‑related costs of $4,412, mainly due to increases in headcount, and annual and other compensation costs, partially offset by lower incentive compensation expense related to the reduction in Gregory S. Bentley’s fractional interest under the amended and restated Bentley Systems, Incorporated Bonus Pool Plan (the “Bonus Plan”) as part of Mr. Bentley’s transition to the role of Executive Chair effective July 1, 2024. Additionally, during the year ended December 31, 2024, we recognized approximately $2,200 of other corporate initiatives expenses, which did not recur in the current year.

Deferred compensation plan. Deferred compensation plan reflects the expense (income) recorded related to changes in deferred compensation plan liabilities, which are marked to market at the end of each reporting period.

For the year ended December 31, 2025, deferred compensation plan expense was attributable to the marked to market impact on deferred compensation plan liability balances period over period.

Amortization of purchased intangibles. Amortization of purchased intangibles includes the amortization of acquired non‑product related intangible assets, primarily customer relationships, trademarks, and non‑compete agreements recorded in connection with completed acquisitions.

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For the year ended December 31, 2025, on a constant currency basis, amortization of purchased intangibles decreased primarily due to previously acquired intangible assets that continue to become fully amortized and lower acquisition activity as compared to prior years.

Interest Expense, Net

% Change
Year Ended December 31,20242023
202520242023to 2025to 2024
Interest expense$(15,322)$(24,774)$(41,331)(38.2%)(40.1%)
Interest income2,8872,7301,5385.8%77.5%
Interest expense, net$(12,435)$(22,044)$(39,793)(43.6%)(44.6%)

Interest expense, net primarily represents interest expense on our credit facility borrowings and outstanding convertible senior notes, amortization of deferred debt issuance costs, and interest income from our investments in money market funds. The majority of our debt is protected from rising interest rates, through either very low fixed coupon interest on our convertible notes or our $200,000 interest rate swap, which expires in 2030.

For the year ended December 31, 2025, interest expense, net decreased primarily due to lower weighted average debt outstanding under the credit facilities as compared to the prior year.

Other Income (Expense), Net

Year Ended December 31,
202520242023
(Loss) gain from:
Change in fair value of interest rate swap$(10,238)$10$(5,038)
Foreign exchange (1)2,5789392,497
Receipts related to interest rate swap7,3909,3098,803
Other income (expense), net (2)8172,691(13,484)
Total other income (expense), net$547$12,949$(7,222)

(1)Foreign exchange gain is primarily attributable to foreign currency translation derived mainly from U.S. dollar denominated cash and cash equivalents, account receivables, customer deposits, and intercompany balances held by foreign subsidiaries.

(2)Other income (expense), net for the year ended December 31, 2023 includes non-marketable equity investment impairment and other charges of $(16,988), partially offset by gains on non-marketable equity investments of $2,360.

Provision (Benefit) for Income Taxes

Year Ended December 31,
202520242023
Income before income taxes$350,733$293,055$183,527
Provision (benefit) for income taxes$72,977$58,726$(143,241)
Effective tax rate20.8%20.0%(78.0%)

Provision (benefit) for income taxes includes the aggregate consolidated income tax expense for U.S. domestic and foreign income taxes.

For the year ended December 31, 2025, the effective tax rate was higher as compared to the year ended December 31, 2024 primarily due to the decrease in tax benefits related to stock‑based compensation, net of the impact from officer compensation limitation provisions, recognized in the current year.

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On July 4, 2025, President Trump signed into law the One Big Beautiful Bill Act (“OBBBA”). The OBBBA includes the permanent extension of certain expiring provisions of the U.S. Tax Cuts and Jobs Act (the “JOBS Act”), modifications to the international tax framework, and the restoration of favorable tax treatment for certain business provisions. The legislation has multiple effective dates. The OBBBA had a favorable impact on our cash paid for income taxes in 2025, with continued cash tax favorability expected in 2026, primarily attributable to the change in restoring immediate U.S. tax deductions for domestic research and development expenses. The OBBBA did not have a material impact on the effective tax rate for the year ended December 31, 2025.

Key Business Metrics:

In addition to our results of operations discussed above, we believe the following presentation of key business metrics provides additional useful information to investors regarding our results of operations. To the extent material, we disclose below the additional purposes, if any, for which our management uses these key business metrics. Our key business metrics may vary significantly from period to period for reasons unrelated to our operating performance and may differ from similarly titled measures presented by other companies.

December 31,
202520242023
ARR$1,462,145$1,283,256$1,174,774
Last twelve-months recurring revenues$1,391,350$1,238,004$1,096,677
Twelve-months ended constant currency (1):
ARR growth rate11.5%12%12.5%
Account retention rate99%99%98%
Recurring revenues dollar-based net retention rate109%110%109%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our definition and our use of constant currency.

Recurring Revenues

Recurring revenues are the basis for our other revenue-related key business metrics. We believe this measure is useful in evaluating our ability to consistently retain and grow our revenues within our existing accounts.

Recurring revenues are subscriptions revenues that recur monthly, quarterly, or annually with specific or automatic renewal clauses and professional services revenues in which the underlying contract is based on a fixed fee and contains automatic annual renewal provisions.

ARR

ARR is a key business metric that we believe is useful in evaluating the scale and growth of our business as well as to assist in the evaluation of underlying trends in our business. Furthermore, we believe ARR, considered in connection with our last twelve‑month recurring revenues dollar‑based net retention rate, is a leading indicator of revenue growth.

ARR is defined as the sum of the annualized value of our portfolio of contracts that produce recurring revenues as of the last day of the reporting period, and the annualized value of the last three months of recognized revenues for our contractually recurring consumption‑based software subscriptions with consumption measurement durations of less than one year, calculated using the spot foreign currency exchange rates. We believe that the last three months of recognized revenues, on an annualized basis, for our recurring software subscriptions with consumption measurement period durations of less than one year is a reasonable estimate of the annual revenues, given our consistently high retention rate and stability of usage under such subscriptions.

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ARR resulting from the annualization of recurring contracts with consumption measurement durations of less than one year, as a percentage of total ARR, was 51%, 50%, and 47% as of December 31, 2025, 2024, and 2023, respectively, with our E365 subscription offering representing 46%, 45%, and 41% of total ARR as of December 31, 2025, 2024, and 2023, respectively.

Constant currency ARR growth rate is the growth rate of ARR measured on a constant currency basis. In reporting period-over-period ARR growth rates in constant currency, we calculate constant currency growth rates by translating current and prior period ARR on a transactional basis to our reporting currency using current year budget exchange rates. We believe that ARR growth is an important metric indicating the scale and growth of our business.

Last Twelve‑Months Recurring Revenues

Last twelve‑month recurring revenues is a key business metric that we believe is useful in evaluating our ability to consistently retain and grow our recurring revenues. We believe that we will continue to experience favorable growth in recurring revenues primarily due to our strong account retention and recurring revenues dollar‑based net retention rates, as well as the addition of new accounts with recurring revenues.

Last twelve‑months recurring revenues is calculated as recurring revenues recognized over the preceding twelve‑month period.

The last twelve‑months recurring revenues for the periods ended December 31, 2025, 2024, and 2023 compared to the last twelve‑months of the comparative twelve‑month period increased by $153,346, $141,327, and $118,653, respectively. This increase was primarily due to growth in ARR, which is primarily the result of growing our recurring revenues within our existing accounts as expressed in our recurring revenues dollar‑based net retention rate, as well as additional recurring revenues resulting from new accounts and acquisitions. For the twelve months ended December 31, 2025, 2024, and 2023, 93%, 91%, and 89%, respectively, of our revenues were recurring revenues.

Account Retention Rate

Account retention rate is a key business metric that we believe is useful in evaluating the long‑term value of our account relationships and our ability to retain our account base. We believe that our consistent and high account retention rates illustrate our ability to retain and cultivate long‑term relationships with our accounts.

Account retention rate for any given twelve-month period is calculated using the average foreign currency exchange rates for the prior period, as follows: the prior period recurring revenues from all accounts with recurring revenues in the current and prior period, divided by total recurring revenues from all accounts during the prior period.

Recurring Revenues Dollar‑Based Net Retention Rate

Recurring revenues dollar‑based net retention rate is a key business metric that we believe is useful in evaluating our ability to consistently retain and grow our recurring revenues.

Recurring revenues dollar‑based net retention rate is calculated, using the average exchange rates for the prior period, as follows: the recurring revenues for the current period, including any growth or reductions from existing accounts, but excluding recurring revenues from any new accounts added during the current period, divided by the total recurring revenues from all accounts during the prior period. A period is defined as any trailing twelve months. Related to our platform acquisitions, recurring revenues into new accounts will be captured as existing accounts starting with the second anniversary of the acquisition when such data conforms to the calculation methodology. This may cause variability in the comparison.

Given that recurring revenues represented 93%, 91%, and 89% of our total revenues for the twelve months ended December 31, 2025, 2024, and 2023, respectively, this metric helps explain our revenue performance as primarily growth from existing accounts.

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Non-GAAP Financial Measures:

In addition to our results determined in accordance with GAAP discussed above, we believe the following presentation of financial measures not in accordance with GAAP provides useful information to investors regarding our results of operations. To the extent material, we disclose below the additional purposes, if any, for which our management uses these non‑GAAP financial measures and provide reconciliations between these non‑GAAP financial measures and their most directly comparable GAAP financial measures. Non‑GAAP financial information should be considered in addition to, not as a substitute for, or in isolation from, the financial information prepared in accordance with GAAP, including operating income, or other measures of performance. Our non‑GAAP financial measures may vary significantly from period to period for reasons unrelated to our operating performance and may differ from similarly titled measures presented by other companies.

Adjusted Operating Income Less Stock-Based Compensation Expense (“AOI less SBC”)

AOI less SBC is a non-GAAP financial measure and is used to measure the operational strength and performance of our business, as well as to assist in the evaluation of underlying trends in our business.

AOI less SBC is defined as operating income adjusted for the following: amortization of purchased intangibles, expense (income) relating to deferred compensation plan liabilities, acquisition expenses (inclusive of cash‑settled retention incentives provided to key employees of acquired companies), and realignment expenses (income), for the respective periods.

AOI less SBC is our primary performance measure, which excludes certain expenses and charges, including the non-cash amortization expense resulting from the acquisition of intangible assets, as we believe these may not be indicative of our core business operating results. We intentionally include stock-based compensation expense in this measure as we believe it better captures the economic costs of our business.

Management uses this non-GAAP financial measure to understand and compare operating results across accounting periods, for internal budgeting and forecasting purposes, to evaluate financial performance, and in our comparison of our financial results to those of other companies. It is also a significant performance measure in certain of our executive incentive compensation programs.

Adjusted Operating Income (“AOI”)

Adjusted operating income is a non-GAAP financial measure that we believe is useful to investors in making comparisons to other companies, although this measure may not be directly comparable to similar measures used by other companies.

Adjusted operating income is defined as operating income adjusted for the following: amortization of purchased intangibles, expense (income) relating to deferred compensation plan liabilities, acquisition expenses (inclusive of cash‑settled retention incentives provided to key employees of acquired companies), realignment expenses (income), and stock‑based compensation expense, for the respective periods.

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Reconciliation of operating income to AOI less SBC and to Adjusted operating income:

Year Ended December 31,
202520242023
Operating income$362,621$302,150$230,542
Amortization of purchased intangibles (1)45,65846,67951,219
Deferred compensation plan (2)14,40912,38213,580
Acquisition expenses (3)7,22910,22217,866
Realignment expenses (4)78911,470
AOI less SBC429,917372,222324,677
Stock-based compensation expense (5)71,94973,50571,470
Adjusted operating income$501,866$445,727$396,147

Further explanation of certain of our adjustments in arriving at AOI less SBC and Adjusted operating income are as follows:

(1)Amortization of purchased intangibles. Amortization of purchased intangibles varies in amount and frequency and is significantly impacted by the timing and size of our acquisitions. Management finds it useful to exclude these non‑cash charges from our operating expenses to assist in budgeting, planning, and forecasting future periods. The use of intangible assets contributed to our revenues earned during the periods presented and will also contribute to our revenues in future periods. Amortization of purchased intangible assets will recur in future periods.

(2)Deferred compensation plan. We exclude Deferred compensation plan expense (income) when we evaluate our continuing operational performance because it is not reflective of our ongoing business and results of operations. We believe it is useful for investors to understand the effects of this item on our total operating expenses. Deferred compensation plan liabilities are marked to market at the end of each reporting period, with changes in the liabilities recorded as an expense (income) to Deferred compensation plan in the consolidated statements of operations.

(3)Acquisition expenses. We incur expenses for professional services rendered in connection with business combinations, which are included in our GAAP presentation of general and administrative expense. Also included in our acquisition expenses are cash‑settled retention incentives provided to key employees of the acquired companies. We exclude these acquisition expenses when we evaluate our continuing operational performance as we would not have otherwise incurred these expenses in the periods presented as part of our continuing operations.

(4)Realignment expenses. We exclude these charges and subsequent adjustments to our estimates when we evaluate our continuing operational performance because they are not reflective of our ongoing business and results of operations. We believe it is useful for investors to understand the effects of these items on our total operating expenses. During the fourth quarter of 2023, we approved the 2023 Program. For the years ended December 31, 2024 and 2023, we recognized realignment costs related to the aforementioned program of $847 and $12,579, respectively, which represent termination benefits for colleagues whose roles were impacted (see Note 21 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K). For the year ended December 31, 2023, realignment expenses were partially offset by income associated with the continued wind down of our Russian entities following our decision to exit the Russian market beginning in the second quarter of 2022.

(5)Stock‑based compensation expense. We exclude non-cash stock‑based compensation expenses from certain of our non‑GAAP measures because we believe this is useful to investors in making comparisons to other companies.

Constant Currency

Constant currency and constant currency growth rates are non-GAAP financial measures that present our results of operations excluding the estimated effects of foreign currency exchange rate fluctuations. A significant amount of our operations is conducted in foreign currencies. As a result, the comparability of the financial results reported in U.S. dollars is affected by changes in foreign currency exchange rates. We use constant currency and constant currency growth rates to evaluate the underlying performance of the business, and we believe it is helpful for investors to present operating results on a comparable basis period over period to evaluate its underlying performance.

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In reporting period‑over‑period results, except for ARR as discussed above in “Key Business Metrics” section, we calculate the effects of foreign currency fluctuations and constant currency information by translating current and prior period results on a transactional basis to our reporting currency using prior period average foreign currency exchange rates in which the transactions occurred.

Reconciliation of consolidated revenues to consolidated revenues in constant currency:

Constant Currency Change 2024 to 2025:

Year Ended December 31, 2025Year Ended December 31, 2024
ActualImpact of Foreign Exchange at 2024 RatesConstant CurrencyActualImpact of Foreign Exchange at 2024 RatesConstant Currency
Subscriptions$1,376,696$(11,533)$1,365,163$1,223,362$(791)$1,222,571
Perpetual licenses46,180(174)46,00645,961(5)45,956
Subscriptions and licenses1,422,876(11,707)1,411,1691,269,323(796)1,268,527
Services78,903(680)78,22383,772(1)83,771
Total revenues$1,501,779$(12,387)$1,489,392$1,353,095$(797)$1,352,298

Constant Currency Change 2023 to 2024:

Year Ended December 31, 2024Year Ended December 31, 2023
ActualImpact of Foreign Exchange at 2023 RatesConstant CurrencyActualImpact of Foreign Exchange at 2023 RatesConstant Currency
Subscriptions$1,223,362$814$1,224,176$1,080,307$(977)$1,079,330
Perpetual licenses45,96132346,28446,038(4)46,034
Subscriptions and licenses1,269,3231,1371,270,4601,126,345(981)1,125,364
Services83,772(291)83,481102,068(61)102,007
Total revenues$1,353,095$846$1,353,941$1,228,413$(1,042)$1,227,371

Reconciliation of revenues by geographic region to revenues by geographic region in constant currency:

Constant Currency Change 2024 to 2025:

Year Ended December 31, 2025Year Ended December 31, 2024
ActualImpact of Foreign Exchange at 2024 RatesConstant CurrencyActualImpact of Foreign Exchange at 2024 RatesConstant Currency
Americas$790,495$1,141$791,636$717,002$(182)$716,820
EMEA436,828(13,073)423,755388,384(383)388,001
APAC274,456(455)274,001247,709(232)247,477
Total revenues$1,501,779$(12,387)$1,489,392$1,353,095$(797)$1,352,298

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Constant Currency Change 2023 to 2024:

Year Ended December 31, 2024Year Ended December 31, 2023
ActualImpact of Foreign Exchange at 2023 RatesConstant CurrencyActualImpact of Foreign Exchange at 2023 RatesConstant Currency
Americas$717,002$1,751$718,753$650,926$(238)$650,688
EMEA388,384(2,754)385,630353,550(118)353,432
APAC247,7091,849249,558223,937(686)223,251
Total revenues$1,353,095$846$1,353,941$1,228,413$(1,042)$1,227,371

Reconciliation of cost of revenues to cost of revenues in constant currency:

Constant Currency Change 2024 to 2025:

Year Ended December 31, 2025Year Ended December 31, 2024
ActualImpact of Foreign Exchange at 2024 RatesConstant CurrencyActualImpact of Foreign Exchange at 2024 RatesConstant Currency
Cost of subscriptions and licenses$201,405$(658)$200,747$173,340$(83)$173,257
Cost of services76,125(729)75,39684,42712184,548
Total cost of revenues$277,530$(1,387)$276,143$257,767$38$257,805

Constant Currency Change 2023 to 2024:

Year Ended December 31, 2024Year Ended December 31, 2023
ActualImpact of Foreign Exchange at 2023 RatesConstant CurrencyActualImpact of Foreign Exchange at 2023 RatesConstant Currency
Cost of subscriptions and licenses$173,340$140$173,480$169,406$22$169,428
Cost of services84,427(101)84,32696,677696,683
Total cost of revenues$257,767$39$257,806$266,083$28$266,111

Reconciliation of operating expenses to operating expenses in constant currency:

Constant Currency Change 2024 to 2025:

Year Ended December 31, 2025Year Ended December 31, 2024
ActualImpact of Foreign Exchange at 2024 RatesConstant CurrencyActualImpact of Foreign Exchange at 2024 RatesConstant Currency
Research and development$307,576$(626)$306,950$281,247$25$281,272
Selling and marketing289,543(1,662)287,881255,177(39)255,138
General and administrative217,332(949)216,383210,374(43)210,331
Deferred compensation plan14,40914,40912,38212,382
Amortization of purchased intangibles32,768(58)32,71033,99833,998
Total operating expenses$861,628$(3,295)$858,333$793,178$(57)$793,121

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Constant Currency Change 2023 to 2024:

Year Ended December 31, 2024Year Ended December 31, 2023
ActualImpact of Foreign Exchange at 2023 RatesConstant CurrencyActualImpact of Foreign Exchange at 2023 RatesConstant Currency
Research and development$281,247$817$282,064$274,619$17$274,636
Selling and marketing255,177505255,682224,336(212)224,124
General and administrative210,374(106)210,268180,738(308)180,430
Deferred compensation plan12,38212,38213,58013,580
Amortization of purchased intangibles33,998(39)33,95938,515(2)38,513
Total operating expenses$793,178$1,177$794,355$731,788$(505)$731,283

Liquidity and Capital Resources:

Cash and Cash Equivalents

December 31,
20252024
Cash and cash equivalents held domestically$39,093$2,845
Cash and cash equivalents held by foreign subsidiaries84,18561,164
Total cash and cash equivalents$123,278$64,009

Our primary source of operating cash is from the sale of our subscriptions, perpetual licenses, and services. Our primary use of cash is payment of our operating costs, which consist mainly of headcount‑related costs. In addition to operating expenses, we also use cash to service our debt obligations, to pay quarterly dividends, to repurchase our Class B common stock and convertible debt, and for capital expenditures in support of our operations. We also use cash to fund our acquisitions of software assets and businesses, and other investment activities.

During the years ended December 31, 2025 and 2024, we made cash repatriations to the U.S. of approximately $180,000 and $138,000, respectively, from earnings generated by our foreign subsidiaries. In 2025 and 2024, the repatriations were primarily used to pay down our credit facility borrowings and to supplement our domestic working capital needs.

We believe that cash generated from operations, together with existing cash and cash equivalent balances, and external borrowings including available liquidity under the Credit Facility, will be sufficient to meet our domestic and international working capital and capital expenditure requirements. We regularly review our capital structure and consider a variety of potential financing alternatives and planning strategies to ensure that we have the proper liquidity available in the locations in which it is needed and to fund our operations and growth investments with cash that has not been permanently reinvested outside the U.S. Our future capital requirements may be materially different than those currently planned in our budgeting and forecasting activities and depend on many factors, including our strategy of regularly acquiring and integrating specialized infrastructure engineering software businesses, our rate of revenue growth, the timing and extent of spending on research and development, the expansion of our sales and marketing activities, the timing of new product introductions, market acceptance of our products, competitive factors, our discretionary payments of dividends or repurchases of our Class B common stock and convertible debt, funding of our purchase commitments, currency fluctuations, and overall economic conditions, globally. To the extent that current and anticipated future sources of liquidity are insufficient to fund our future business activities and requirements, we may be required to seek additional equity or debt financing. The sale of additional equity would result in additional dilution to our stockholders, while the incurrence of additional debt financing, including convertible debt, would result in additional debt service obligations. Such debt instruments also could introduce new or modified covenants that might restrict our operations and/or our ability to pay dividends,

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consummate acquisitions, or otherwise pursue our business strategies. We cannot provide assurance that we could obtain additional financing on favorable terms or at all.

Cash Flows Activity

Year Ended December 31,
202520242023
Net cash provided by (used in):
Operating activities$538,464$435,292$416,696
Investing activities$(112,309)$(143,267)$(60,504)
Financing activities$(376,298)$(289,850)$(359,074)

Operating Activities

For the year ended December 31, 2025, compared to the prior year, net cash provided by operating activities was higher by $103,172 due to an increase in net income of $43,361, an increase in net cash flows from the change in operating assets and liabilities of $36,777, and a net increase in non‑cash adjustments of $23,034. The increase in net cash flows from the change in operating assets and liabilities year over year was primarily due to higher deferred revenues, timing of collections on our receivables, higher accounts payable, lower capitalized internal-use software implementation costs, as well as the overall timing of payments for software maintenance contracts. Offsetting these increases were lower period over period Cloud Services Subscription deposits and lower accruals and other current liabilities.

Investing Activities

Net cash used in investing activities was lower by $30,958 for the year ended December 31, 2025, compared to the prior year, primarily due to lower acquisition related payments of $37,155. We used available cash and borrowings under our credit facilities to fund our acquisitions.

Financing Activities

Net cash used in financing activities was higher by $86,448 for the year ended December 31, 2025, compared to the prior year, primarily due to higher payments for shares acquired of $80,381, including shares repurchased under the BSY Stock Repurchase Program (the “Repurchase Program”) and higher dividend payments of $12,848, primarily due to an increase in our quarterly dividend per share to $0.07 in 2025 from $0.06 in 2024, partially offset by lower net paydowns of the credit facilities of $11,398. Additionally, we paid $9,797 in cash to repurchase $10,000 aggregate principal amount of our outstanding 2026 Notes during the first quarter of 2025.

Long-Term Debt

December 31,
20252024
Current portion of long-term debt$$
Long-term debt1,248,9121,388,088
Total debt$1,248,912$1,388,088

On October 18, 2024, we entered into the Credit Facility, which provides us with a $1,300,000 revolving credit facility, including a $125,000 swingline loan and $125,000 in letters of credit. The Credit Facility also provides us with a $500,000 “accordion” feature to increase the facility in the form of both revolving indebtedness and/or incremental term loans. On October 18, 2024, we used borrowings under the Credit Facility to repay all indebtedness outstanding under the 2017 Credit Facility, including the outstanding senior secured term loan.

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As of December 31, 2025, we had $1,299,850 available under the Credit Facility, and we were in compliance with all covenants under the Credit Facility, the 2026 Notes, and the 2027 Notes. Any failure to comply with such covenants under the Credit Facility would prevent us from being able to borrow additional funds under the Credit Facility, and, as with any failure to comply with such covenants under the 2026 Notes and the 2027 Notes, could constitute a default that may cause all amounts outstanding to become due and immediately payable in full.

As of December 31, 2025, the 2026 Notes were classified as long‑term in the consolidated balance sheets as we had the ability and intent to refinance them on a long‑term basis through available capacity under the Credit Facility.

The 2026 Notes matured on January 15, 2026. Upon maturity, we repaid $678,254, which consisted of the remaining outstanding principal balance and accrued interest on the 2026 Notes using borrowings under the Credit Facility and available cash on hand.

Our credit facilities, 2026 Notes, and 2027 Notes are described in Note 10 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K.

Stock Repurchases

BSY Stock Repurchase Program

Our Board of Directors had authorized us to repurchase up to $200,000 of our Class B common stock and/or outstanding convertible senior notes through June 30, 2024 under the Repurchase Program. This authorization under the Repurchase Program expired on June 30, 2024. In March 2024, our Board of Directors approved an extension to the Repurchase Program authorizing us to repurchase up to $200,000 of our Class B common stock and/or outstanding convertible senior notes from June 30, 2024 through June 30, 2026. In November 2025, our Board of Directors approved an extension to the Repurchase Program authorizing us to repurchase up to $500,000 of our Class B common stock and/or outstanding convertible senior notes from November 21, 2025 through December 31, 2028. This updated authorization supersedes our prior authorization, which was set to expire on June 30, 2026. We may use available working capital, cash provided by operating activities, and/or external borrowings including available liquidity under our Credit Facility to make repurchases.

During the year ended December 31, 2025, we repurchased 2,887,224 shares for $125,057, and $10,000 aggregate principal amount of our outstanding 2026 Notes for $9,797 under the Repurchase Program. During the year ended December 31, 2024, we repurchased 1,292,733 shares for $64,359 under the Repurchase Program.

The timing, as well as the number and value of shares and/or outstanding convertible senior notes repurchased under the Repurchase Program, will be determined at our discretion and will depend on a variety of factors, including our assessment of the intrinsic value of our shares, the market price of our Class B common stock and outstanding convertible senior notes, general market and economic conditions, available liquidity, compliance with our debt and other agreements, and applicable legal requirements.

Withholding Taxes on Certain Equity Awards

We have the right to require that certain equity awardees receive gross or net quantities of shares of our Class B common stock, including distributions from the DCP and share issuances under the Bonus Plan. In the case of a gross issuance or distribution, an awardee is required to reimburse promptly to us the cash required for his or her tax withholding amounts. Conversely, under a net issuance or distribution, shares are withheld in consideration of remitting withholding taxes on behalf of an equity awardee, thereby requiring us to remit cash for the tax withholdings. We exercised our right to require that impacted equity awardees receive gross quantities of our Class B common stock during the first quarter of 2025, but we allowed impacted awardees the option to receive net quantities of shares of our Class B common stock during the second, third, and fourth quarters of 2025. During the year ended December 31, 2024, we exercised our right to require that impacted equity awardees receive gross quantities of our Class B common stock. We will continue to evaluate whether share awards will be required to be received by awardees on a gross basis, or if net settlement may be elected by awardees.

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Dividend Payments

The declaration and payment of dividends is within the discretion of our Board of Directors. We paid quarterly dividends of $0.07 per share of common stock during the year ended December 31, 2025 and $0.06 per share of common stock during the year ended December 31, 2024. While we intend to continue paying quarterly dividends, any future determination will be subject to the discretion of our Board of Directors and will be dependent on a number of factors, including our results of operations, capital requirements, restrictions under Delaware law, and overall financial condition, as well as any other factors our Board of Directors considers relevant. In addition, the terms of the agreement governing the Credit Facility limit the amount of dividends we can pay.

Contractual Obligations and Other Commitments:

The following table summarizes our most significant contractual obligations as of December 31, 2025:

TotalDue within 12 monthsDue after 12 months
Debt Obligations (1)$1,252,830$677,830$575,000
Purchase Obligations$53,700$17,600$36,100
DCP Obligations$111,125$4,294$106,831

(1)Amounts represent the face value of debt and exclude interest payments.

Our largest contractual obligations relate to our outstanding debt, which include convertible notes due in 2026 and 2027. We repaid the 2026 Notes upon maturity on January 15, 2026. Our Credit Facility matures on October 18, 2029, subject to a “revolving maturity date” on the date that is 91 days prior to the maturity date of our outstanding convertible debt, unless on such date we meet certain liquidity requirements. We typically fund and expect to continue to fund debt maturities and interest payments with cash flows generated from operations, existing cash and cash equivalents, or proceeds from additional financing. If an early conversion notice is received, we have the option to pay cash, deliver shares of our Class B common stock, or a combination thereof. See Note 10 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our debt obligations.

We have non‑cancelable future cash purchase commitments for services related to cloud provisioning of our software and for internal‑use software costs. Our purchase obligations are in addition to amounts included in our consolidated balance sheets. We have funded and expect to continue to be able to fund our purchase obligations with cash flows generated from operations, existing cash and cash equivalents or revolving loan borrowings under the Credit Facility. See Note 18 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our purchase obligations.

Our DCP obligations represent DCP participants’ holdings in phantom investment funds, which are classified as liabilities as they will be settled in cash upon eventual distribution. We have funded and expect to continue to be able to fund our DCP obligations with cash flows generated from operations, existing cash and cash equivalents, or revolving loan borrowings under the Credit Facility. See Note 12 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our DCP obligations.

Our other future contractual obligations are related to leases. See Note 8 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our lease obligations.

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Critical Accounting Estimates:

The preparation of our consolidated financial statements in conformity with GAAP requires us to make estimates that affect the reported amounts of assets, liabilities, revenues, and expenses, and the related disclosure of contingent assets and contingent liabilities. We base our judgments on our historical experience and on various other assumptions that we believe are reasonable under the circumstances, the results of which form the basis for making estimates about the carrying value of assets and liabilities that are not readily apparent from other sources. Actual results may differ from these estimates under different assumptions or conditions.

Revenue Recognition

Our contracts with customers may include promises to transfer licenses (perpetual or term‑based), maintenance, and services to a user. Judgment is required to determine if the promises are separate performance obligations, and if so, the allocation of the transaction price to each performance obligation. When an arrangement includes multiple performance obligations which are concurrently delivered and have the same pattern of transfer to the customer, we account for those performance obligations as a single performance obligation. For contracts with more than one performance obligation, the transaction price is allocated among the performance obligations in an amount that depicts the relative standalone selling price (“SSP”) of each obligation. Judgment is required to determine the SSP for each distinct performance obligation. In instances where SSP is not directly observable, such as when we do not sell the product or service separately, we determine the SSP using information that may include market conditions and other observable inputs. We use a range of amounts to estimate SSP when we sell each of the products and services separately and need to determine whether there is a discount that should be allocated based on the relative SSP of the various products and services.

Our SELECT agreement provides users with perpetual licenses a right to exchange software for other eligible perpetual licenses on an annual basis upon renewal. We refer to this option as portfolio balancing and concluded that the portfolio balancing feature represents a material right resulting in the deferral of the associated revenue. Judgment is required to estimate the percentage of users who may elect to portfolio balance and considers inputs such as historical user elections. This feature is available once per term and must be exercised prior to the respective renewal term. We recognize the associated revenue upon election or when the portfolio balancing right expires. This right is included in the initial and subsequent renewal terms and we reestablish the revenue deferral for the material right upon the beginning of the renewal term. Portfolio balancing exchange rights are included in Deferred revenues in the consolidated balance sheets.

Goodwill and Other Intangible Assets

Intangible assets primarily arise from acquisitions and principally consist of goodwill, acquired software and technology, customer relationships, and trademarks. Finite-lived intangible assets are amortized on a straight‑line basis over their estimated useful lives.

Goodwill

Goodwill consists of the excess of cost over the fair value of net assets acquired in business combinations. Goodwill is not amortized but instead is tested annually for impairment on October 1, or more frequently if events occur or circumstances change that would more likely than not reduce its fair value below its carrying amount. We allocate goodwill to reporting units on a relative fair value basis.

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In testing for goodwill impairment, we may first qualitatively assess whether it is more likely than not (a likelihood of more than 50 percent) that a goodwill impairment exists. If it is determined that a quantitative assessment is required and the carrying amount exceeds its fair value, we will recognize goodwill impairment in the amount in which the carrying amount of the reporting unit exceeds its fair value, but not to exceed the carrying amount of goodwill within the reporting unit. The process of evaluating the potential impairment of goodwill is subjective and requires significant judgment at many points in the process. The value of our goodwill could also be impacted by future adverse changes including declines in our stock price, market capitalization, or cash flows, and slower growth rates in our industry. There was no impairment of goodwill as a result of our annual impairment assessments conducted for the years ended December 31, 2025, 2024, or 2023.

Other Intangible Assets

We evaluate intangible assets subject to amortization for impairment whenever events or changes in circumstances indicate that the carrying value of these assets may not be recoverable or that useful lives of those assets are no longer appropriate. If circumstances require an asset to be tested for possible impairment, we first compare the undiscounted cash flows expected to be generated by that asset to its carrying value. If the carrying value of the asset is not recoverable on an undiscounted cash flow basis, an impairment is recognized to the extent that the carrying value exceeds its fair value. The process of evaluating the potential impairment of intangible assets is subjective and requires significant judgment at many points in the process. There was no impairment of intangible assets subject to amortization for the years ended December 31, 2025, 2024, or 2023.

Income Taxes

We account for income taxes under the asset and liability method, which requires the recognition of deferred tax assets and liabilities for the expected future tax consequences of events that have been included in the consolidated financial statements. Under this method, deferred tax assets and liabilities are determined based on net operating loss (“NOL”) carryforwards, credit carryforwards, and temporary differences between the financial statement and tax basis of assets and liabilities using enacted tax rates in effect for the year in which the items are expected to reverse. The effect of a change in tax rates on deferred tax assets and liabilities is recognized in income in the period of the enactment date.

We perform a quarterly assessment of the recoverability of the net deferred tax assets. We consider all available evidence, both positive and negative, in determining whether all or a portion of a deferred tax asset is more likely than not to be realized. In the event we determine that all or a portion of the deferred tax assets is not more likely than not to be realized, an adjustment to the valuation allowance would be recorded that would increase the provision for income taxes. To the extent that the realization of a deferred tax asset is based upon forecasted future earnings, our judgment regarding future profitability may change due to future market conditions and other factors. Assumptions about future taxable income require significant judgment and, while these assumptions rely heavily on estimates, such estimates are consistent with the plans we are using to manage the underlying business. Any change in future profitability may require material adjustments to these net deferred tax assets, resulting in a reduction in net income in the period when such determination is made. Additionally, future changes in tax laws and rates, including administrative or regulatory guidance, could affect recorded deferred tax assets and liabilities. Any adjustments to these estimates will generally be recorded as an income tax expense or benefit in the period the adjustment is determined.

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We are subject to income taxes in the U.S. and in numerous foreign jurisdictions. The calculation of our tax liabilities often involves dealing with uncertainties in the application of complex tax laws and regulations in a multitude of jurisdictions across our global operations. There are many transactions and calculations about which the ultimate tax outcome is uncertain. A benefit from an uncertain tax position may be recognized when it is more likely than not that the position will be sustained based upon the technical merits of the position. This may include expected resolutions upon examination, any related appeals, or through a litigation processes. As a result, our calculations involve estimates by management. Due to the complexity of some of these uncertainties, the ultimate resolution may result in a payment, potentially including interest and penalties, that is materially different from our current estimates of the unrecognized tax benefit liabilities. These differences, along with any related interest and penalties, will generally be reflected as increases or decreases to income tax expense in the period in which new information becomes available. We review the tax reserves as circumstances warrant and adjust the reserves as events occur that affect our potential liability for additional taxes. We follow the applicable guidance on derecognition, classification, interest and penalties, accounting in interim periods, disclosure, and transition with respect to uncertain tax positions. We recognize interest and penalties related to income taxes within the (Provision) benefit for income taxes line in the consolidated statements of operations. Accrued interest and penalties are included within the related tax liability line in the consolidated balance sheets.

MD&A history

Prior-year 10-K MD&A spans are extracted from SEC filings with the same bounded parser used for the latest filing. The latest 10-K appears above; prior years are below.

FY 2024 10-K MD&A

SEC filing source: 0001031308-25-000002.

Extracted structurally from real Item 7 body heading to real Item 7A/8 boundary. Confidence: high. Filing date: 2025-02-26. Report date: 2024-12-31.

Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations

The following discussion should be read in conjunction with our audited consolidated financial statements and notes thereto included in Part II, Item 8 of this Annual Report on Form 10‑K. In addition to historical information, this discussion contains forward‑looking statements that involve risks, uncertainties, and assumptions that could cause actual results to differ materially from management’s expectations. Factors that could cause such differences are set forth in Part I, Item 1A. Risk Factors of this Annual Report on Form 10‑K. Refer to Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations in our 2023 Annual Report on Form 10‑K for management’s discussion and analysis of financial condition and results of operations for the year ended December 31, 2023 compared to the year ended December 31, 2022.

All amounts presented in this Management’s Discussion and Analysis of Financial Condition and Results of Operations, except share and per share amounts, are presented in thousands. Additionally, many of the amounts and percentages have been rounded for convenience of presentation. Minor differences in totals and percentage calculations may exist due to rounding.

Overview:

Bentley Systems is the infrastructure engineering software company. Our purpose is to advance the world’s infrastructure for better quality of life. We empower people to design, build, and operate better and more resilient infrastructure through the adoption of our intelligent digital twin solutions. We manage our business globally within one reportable segment, the development and marketing of computer software and related services, which is consistent with how our chief operating decision maker (“CODM”) reviews and manages our business.

Executive Summary:

•Total revenues were $1,353,095 for the year ended December 31, 2024, up 10.1% or 10.3% on a constant currency basis(1) compared to the prior year;

•Subscriptions revenues were $1,223,362 for the year ended December 31, 2024, up 13.2% or 13.4% on a constant currency basis(1) compared to the prior year;

•ARR(2) was $1,283,256 as of December 31, 2024, compared to $1,174,774 as of December 31, 2023, representing a constant currency(1) ARR growth rate(2) of 12%;

•Last twelve-month recurring revenues dollar-based net retention rate(2) was 110% as of December 31, 2024, compared to 109% as of December 31, 2023;

•Operating income was $302,150 for the year ended December 31, 2024, compared to $230,542 for the prior year;

•Adjusted operating income inclusive of stock-based compensation expense (“Adjusted OI w/SBC”)(1) was $372,222 for the year ended December 31, 2024, compared to $324,677 for the prior year; and

•Cash flows from operations was $435,292 for the year ended December 31, 2024, compared to $416,696 for the prior year.

(1)Constant currency and Adjusted OI w/SBC are non‑GAAP financial measures. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our definitions and our uses of constant currency and Adjusted OI w/SBC.

(2)Refer to the “Key Business Metrics” section for additional information, including our definitions and our uses of ARR, ARR growth rate, and recurring revenues dollar-based net retention rate.

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Results of Operations:

Impact of Foreign Currency

Our results of operations have been, and in the future will be, affected by changes in foreign currency exchange rates. For the years ended December 31, 2024, 2023, and 2022, approximately 34%, 35%, and 36%, respectively, of our total revenues and 42%, 45%, and 46%, respectively, of our total operating expenses were denominated in a currency other than the U.S. dollar including most significantly: euros, British pounds, Canadian dollars, Australian dollars, Chinese yuan renminbi, and New Zealand dollars. Other than the natural hedge attributable to matching revenues and expenses in the same currencies, we do not currently hedge foreign currency exposure.

We identify the effects of foreign currency on our operations and present constant currency growth rates and fluctuations because we believe exchange rates are an important factor in understanding period‑over‑period comparisons and enhance the understanding of our results and evaluation of our performance. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our definition and our use of constant currency.

Revenues

We generate revenues from subscriptions, perpetual licenses, and services. Our total revenues are diversified by account type, size, and geography. Our sources of revenue growth, excluding the impact from acquisitions, primarily come from additional subscriptions revenues from existing accounts using the same products and represent the majority of our revenue growth, additional subscriptions revenues from existing accounts using new products, and subscriptions revenues from new accounts. We believe that we have a loyal account base, with over 70% of our total revenues for the years ended December 31, 2024, 2023, and 2022 generated from organizations that have been our accounts for over ten years.

In addition to our results of operations discussed below, the following is supplemental data of our revenues:

Year Ended December 31,
(as a percentage of total revenues)202420232022
Revenues from:
Direct sales channels93%92%92%
Indirect channel partners7%8%8%
Revenues from:
Subscriptions90%88%87%
Recurring services1%1%2%
Total recurring revenues91%89%89%
Perpetual licenses and other services9%11%11%
Largest account represents no more than2%2%2%

The volume, mix, and duration of contract types starting or renewing in any given period may have a material impact on revenue in the period, and as a result can impact the comparability of reported revenue period-over-period. Our subscriptions, perpetual licenses, and services offerings are recognized pursuant to applicable GAAP guidance. See Note 3 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our revenues. We believe that subscription revenues will continue to comprise a majority of our total revenues.

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Consolidated Revenues

% Change% Change
2023 to 20242022 to 2023
ConstantConstant
Year Ended December 31,CurrencyCurrency
202420232022%%(1)%%(1)
Subscriptions$1,223,362$1,080,307$960,22013.2%13.4%12.5%12.5%
Perpetual licenses45,96146,03843,377(0.2%)0.5%6.1%7.3%
Subscriptions and licenses1,269,3231,126,3451,003,59712.7%12.9%12.2%12.3%
Services83,772102,06895,485(17.9%)(18.2%)6.9%7.5%
Total revenues$1,353,095$1,228,413$1,099,08210.1%10.3%11.8%11.9%

(1)Constant currency is a non‑GAAP financial measure. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our prior definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

The increase in total revenues for the year ended December 31, 2024 was driven by an increase in subscriptions revenues, partially offset by decreases in services revenues.

Subscriptions. For the year ended December 31, 2024, the increase in subscriptions revenues was primarily driven by improvements in our business performance of $143,055 ($144,846 on a constant currency basis). Our business performance includes the impact from programmatic acquisitions, which generally are immaterial, individually and in the aggregate.

For the year ended December 31, 2024, the improvements in business performance were primarily driven by expansion from accounts with revenues in the prior period (“existing accounts”), and growth of 3% attributable to new accounts, most notably small- and medium-sized accounts. Improvements in business performance for the year ended December 31, 2024 were led by our engineering applications, followed by Seequent geoprofessional applications, and our Bentley Infrastructure Cloud for project delivery.

Perpetual licenses. For the year ended December 31, 2024, perpetual licenses revenues were flat compared to the prior year.

Services. For the year ended December 31, 2024, the decrease in services revenues was driven by a decline in our business performance of $18,296 ($18,526 on a constant currency basis), driven primarily from weakness in Maximo-related work within our digital integrator, Cohesive.

Revenues by Geographic Region

Revenue from external customers is attributed to individual countries based upon the location of the customer.

% Change% Change
2023 to 20242022 to 2023
ConstantConstant
Year Ended December 31,CurrencyCurrency
202420232022%%(1)%%(1)
Americas$717,002$650,926$584,79410.2%10.5%11.3%11.4%
EMEA388,384353,550312,8049.9%9.1%13.0%12.1%
APAC247,709223,937201,48410.6%11.8%11.1%13.0%
Total revenues$1,353,095$1,228,413$1,099,08210.1%10.3%11.8%11.9%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our prior definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

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Americas. For the year ended December 31, 2024, the increase in revenues from the Americas was primarily driven by improvements in our business performance of $66,076 ($68,067 on a constant currency basis).

The improvements in business performance for the year ended December 31, 2024 were primarily due to expansion of our subscriptions revenues from existing accounts in the U.S., partially offset by a decline in services revenues.

EMEA. For the year ended December 31, 2024, the increase in revenues from EMEA was primarily driven by improvements in our business performance of $34,834 ($32,195 on a constant currency basis).

The improvements in business performance for the year ended December 31, 2024 were primarily due to expansion of our subscriptions revenues from existing accounts in the United Kingdom (“U.K.”), the Middle East, and Africa, partially offset by a decline in services revenues.

APAC. For the year ended December 31, 2024, the increase in revenues from APAC was primarily driven by improvements in our business performance of $23,772 ($26,308 on a constant currency basis).

The improvements in business performance for the year ended December 31, 2024 were primarily due to expansion of our subscriptions revenues from existing accounts in Australia, Southeast Asia, and India, partially offset by declines of our subscriptions revenues from existing accounts in China.

The future results in China remain uncertain as a result of continued geopolitical challenges, the obstacles there to cloud‑deployed software, and the financial timing impact of the preference there for license sales, rather than subscriptions.

Cost of Revenues and Operating Expenses

Headcount-Related Costs

For the years ended December 31, 2024, 2023, and 2022, approximately 80% of our aggregate cost of revenues, research and development, selling and marketing, and general and administrative expenses were represented by what we refer to herein as “headcount‑related” costs. These costs primarily include salaries, benefits, bonuses, stock‑based compensation expense, employment taxes, travel, training, and realignment of our colleagues, and third‑party personnel expenses and related overhead. Our headcount‑related costs are variable in nature. We actively manage these costs to align to our trending run rate of revenue performance, with the objective of enhancing visibility and predictability of resulting operating profit margins.

During the fourth quarter of 2023, the Company approved a strategic realignment program to better serve our accounts and to better align resources with the strategy of the business, including reinvestment in go-to-market functions, as well as in AI in product development (the “2023 Program”). The realignment program resulted in realignment costs of $847 and $12,579 for the years ended December 31, 2024 and 2023, respectively, which represent termination benefits for colleagues whose roles were impacted (less than five percent of total headcount). See Note 21 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information. The realignment program activities have been broadly implemented across our various businesses, which were substantially completed by the end of the second quarter of 2024, and payment of termination benefits were completed as of December 31, 2024. The impact of the realignment program on headcount-related costs for the year ended December 31, 2024 and 2023 is included in our discussion below.

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Cost of Revenues

% Change% Change
2023 to 20242022 to 2023
ConstantConstant
Year Ended December 31,CurrencyCurrency
202420232022%%(1)%%(1)
Cost of subscriptions and licenses$173,340$169,406$147,5782.3%2.4%14.8%15.1%
Cost of services84,42796,67789,435(12.7%)(12.8%)8.1%9.0%
Total cost of revenues$257,767$266,083$237,013(3.1%)(3.1%)12.3%12.8%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our prior definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

Cost of subscriptions and licenses. Cost of subscriptions and licenses expenses primarily include headcount‑related costs, as well as cloud‑related costs incurred for servicing our accounts using cloud provisioned solutions and our license administration platform. Cost of subscriptions and licenses expenses also include channel partner compensation for providing sales coverage to users, depreciation of property and equipment, amortization of capitalized software costs associated with servicing software subscriptions and our Accelerated Commercial Development Program (“ACDP”), and amortization of intangible assets associated with acquired software and technology.

For the year ended December 31, 2024, on a constant currency basis, cost of subscriptions and licenses expenses increased primarily due to an increase in cloud‑related costs of $10,859. Partially offsetting this increase was lower amortization of capitalized costs under our ACDP of $3,983 as compared to the prior year and lower headcount‑related costs of $2,090 primarily due to lower stock‑based compensation expense.

Cost of services. Cost of services expenses primarily include headcount‑related costs, as well as depreciation of property and equipment and amortization of capitalized software costs used for providing training, implementation, configuration, and customization services to accounts.

For the year ended December 31, 2024, on a constant currency basis, cost of services expenses decreased primarily due to a decrease in headcount‑related costs of $12,514, mainly due to a reduction in third‑party personnel costs.

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Operating Expenses

% Change% Change
2023 to 20242022 to 2023
ConstantConstant
Year Ended December 31,CurrencyCurrency
202420232022%%(1)%%(1)
Research and development$281,247$274,619$257,8562.4%2.7%6.5%7.5%
Selling and marketing255,177224,336195,62213.7%14.1%14.7%14.9%
General and administrative210,374180,738174,64716.4%16.5%3.5%3.6%
Deferred compensation plan12,38213,580(15,782)(8.8%)(8.8%)NMNM
Amortization of purchased intangibles33,99838,51541,114(11.7%)(11.8%)(6.3%)(6.3%)
Total operating expenses$793,178$731,788$653,4578.4%8.6%12.0%12.5%

Percentage changes that are considered not meaningful are denoted with NM.

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our prior definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

Research and development. Research and development expenses primarily consist of headcount‑related costs, including costs to develop software products or the software component of products to be sold, leased, or marketed to external accounts, before technological feasibility is reached, which is generally shortly before the release of such products. Our research and development roadmap balances technology advances and new offerings with continuous enhancements to existing offerings. Our allocation of research and development resources is based on a cost‑benefit analysis of acquiring available technology in the marketplace versus developing our own solutions. We anticipate that we will continue to make substantial investments in research and development because we believe the infrastructure engineering software market presents compelling opportunities for the application of new technologies that advance our current solutions.

For the year ended December 31, 2024, on a constant currency basis, research and development expenses increased primarily due to an increase in headcount‑related costs of $9,513, mainly due to an increase in annual and other compensation costs. Offsetting the increase in headcount‑related costs were $4,995 of realignment expenses related to the 2023 Program recorded during the year ended December 31, 2023.

For the year ended December 31, 2024, our research and development headcount‑related costs reflect run‑rate savings associated with the 2023 Program, which we initiated during the fourth quarter of 2023. While most of the realignment actions were completed at the beginning of 2024, our reinvestment of these run‑rate savings into priority investment areas, such as AI in product development, was not fully realized until the third quarter of 2024.

Selling and marketing. Selling and marketing expenses primarily include headcount‑related costs, as well as the expense of online marketing, product marketing and other brand‑building activities, such as advertising, trade shows, and expositions, and various sales and promotional programs. We anticipate that we will continue to make strategic investments in our global business systems and methods to enhance major account sales activities and to support our worldwide sales and marketing strategies, and the business in general.

For the year ended December 31, 2024, on a constant currency basis, selling and marketing expenses increased primarily due to an increase in headcount‑related costs of $23,408, mainly due to an increase in annual and other compensation costs, and an increase in third-party personnel costs primarily related to our marketing activities. Additionally, selling and marketing expenses further increased due to an increase in promotional costs of $5,449.

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General and administrative. General and administrative expenses primarily include headcount‑related costs for our finance, human resources, and legal functions, as well as professional fees for legal and accounting services. General and administrative expenses also include acquisition costs, which consist of costs related to legal, accounting, valuation, insurance, and other consulting and transaction fees. Acquisition costs may drive fluctuations in general and administrative expenses depending on the timing of business combinations.

For the year ended December 31, 2024, on a constant currency basis, general and administrative expenses increased primarily due to an increase in headcount‑related costs of $11,048, mainly due to an increase in annual and other compensation costs, and to a lesser extent, higher charitable contributions focusing on education and sustainability of $4,143 and higher expense associated with non‑income related taxes of $3,585. Additionally, during the year ended December 31, 2024, we recognized approximately $10,300 of costs associated with our internal-use software implementations, as well as approximately $2,200 of other corporate initiatives expenses. Partially offsetting these increases were lower acquisition costs of $4,276.

Deferred compensation plan. Deferred compensation plan reflects the expense (income) recorded related to changes in deferred compensation plan liabilities, which are marked to market at the end of each reporting period.

For the year ended December 31, 2024, deferred compensation plan expense was attributable to the marked to market impact on deferred compensation plan liability balances period over period.

Amortization of purchased intangibles. Amortization of purchased intangibles includes the amortization of acquired non‑product related intangible assets, primarily customer relationships, trademarks, and non‑compete agreements recorded in connection with completed acquisitions.

For the year ended December 31, 2024, on a constant currency basis, amortization of purchased intangibles decreased primarily due to previously acquired intangible assets that continue to become fully amortized and lower acquisition activity as compared to prior years.

Interest Expense, Net

% Change
Year Ended December 31,20232022
202420232022to 2024to 2023
Interest expense$(24,774)$(41,331)$(35,056)(40.1%)17.9%
Interest income2,7301,53842177.5%NM
Interest expense, net$(22,044)$(39,793)$(34,635)(44.6%)14.9%

Percentage changes that are considered not meaningful are denoted with NM.

Interest expense, net primarily represents interest associated with credit facility borrowings, the 2026 Notes, the 2027 Notes, amortization of deferred debt issuance costs, and interest income from our investments in money market funds. The majority of our debt is protected from rising interest rates, through either very low fixed coupon interest on our convertible notes or our $200,000 interest rate swap, which expires in 2030.

For the year ended December 31, 2024, interest expense, net decreased primarily due to lower weighted average debt outstanding, as compared to the prior year, mainly related to the continued pay down of our revolving loan borrowings, and repayments of our senior secured term loan during 2024 under our amended and restated credit agreement, entered into on December 19, 2017 (the “2017 Credit Facility”).

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Other Income (Expense), Net

Year Ended December 31,
202420232022
Gain (loss) from:
Change in fair value of interest rate swap$10$(5,038)$27,083
Foreign exchange (1)9392,497(9,901)
Sale of aircraft2,029
Change in fair value of acquisition contingent consideration1,427
Receipts related to interest rate swap9,3098,8031,947
Other income (expense), net (2)2,691(13,484)1,713
Total other income (expense), net$12,949$(7,222)$24,298

(1)Foreign exchange gain (loss) is primarily attributable to foreign currency translation derived mainly from U.S. dollar denominated cash and cash equivalents, account receivables, customer deposits, and intercompany balances held by foreign subsidiaries.

(2)Other income (expense), net for the year ended December 31, 2023 includes investment impairment and other charges of $(16,988), partially offset by gains on investments of $2,360.

Provision (Benefit) for Income Taxes

Year Ended December 31,
202420232022
Income before income taxes$293,055$183,527$198,275
Provision (benefit) for income taxes$58,726$(143,241)$21,283
Effective tax rate20.0%(78.0)%10.7%

Provision (benefit) for income taxes includes the aggregate consolidated income tax expense for U.S. domestic and foreign income taxes.

For the year ended December 31, 2024, the effective tax rate was higher as compared to the year ended December 31, 2023 primarily due to the discrete tax benefit recognized as a result of the internal legal entity restructuring during the fourth quarter of 2023 described below, as well as a decrease in discrete tax benefits related to stock‑based compensation, net of the impact from officer compensation limitation provisions, partially offset by the decrease in the adverse effective tax rate impact of the net tax on foreign earnings. The decrease in net tax on foreign earnings is primarily related to increased foreign creditable taxes available to reduce the net impact of the U.S. Global Intangible Low‑Taxed Income (“GILTI”) inclusion. For the years ended December 31, 2024 and 2023, we recorded discrete tax benefits of $5,583 and $14,648, respectively, associated with windfall tax benefits from stock‑based compensation, net of the impact from officer compensation limitation provisions.

During the fourth quarter of 2023, we recognized a net discrete income tax benefit of $170,784 attributable to internal legal entity restructuring and related intra-entity transactions as part of our continuing efforts to align intellectual property ownership with our business operating model. These transactions resulted in the recognition of deferred tax benefits arising from the net increase in deferred tax assets related to intangibles and goodwill of $171,622. As of December 31, 2023, the deferred tax assets represented the undiscounted future anticipated cash tax impacts of basis differences, which were expected to be realized through tax amortization over the next 13 years, beginning in 2024. See Note 16 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information.

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Key Business Metrics:

In addition to our results of operations discussed above, we believe the following presentation of key business metrics provides additional useful information to investors regarding our results of operations. To the extent material, we disclose below the additional purposes, if any, for which our management uses these key business metrics. Our key business metrics may vary significantly from period to period for reasons unrelated to our operating performance and may differ from similarly titled measures presented by other companies.

December 31,
202420232022
ARR$1,283,256$1,174,774$1,036,548
Last twelve-months recurring revenues$1,238,004$1,096,677$978,024
Twelve-months ended constant currency (1):
ARR growth rate12%12.5%15%
Account retention rate99%98%98%
Recurring revenues dollar-based net retention rate110%109%110%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our definition and our use of constant currency.

Recurring Revenues

Recurring revenues are the basis for our other revenue-related key business metrics. We believe this measure is useful in evaluating our ability to consistently retain and grow our revenues within our existing accounts.

Recurring revenues are subscriptions revenues that recur monthly, quarterly, or annually with specific or automatic renewal clauses and professional services revenues in which the underlying contract is based on a fixed fee and contains automatic annual renewal provisions.

ARR

ARR is a key business metric that we believe is useful in evaluating the scale and growth of our business as well as to assist in the evaluation of underlying trends in our business. Furthermore, we believe ARR, considered in connection with our last twelve‑month recurring revenues dollar‑based net retention rate, is a leading indicator of revenue growth.

ARR is defined as the sum of the annualized value of our portfolio of contracts that produce recurring revenues as of the last day of the reporting period, and the annualized value of the last three months of recognized revenues for our contractually recurring consumption‑based software subscriptions with consumption measurement durations of less than one year, calculated using the spot foreign currency exchange rates. We believe that the last three months of recognized revenues, on an annualized basis, for our recurring software subscriptions with consumption measurement period durations of less than one year is a reasonable estimate of the annual revenues, given our consistently high retention rate and stability of usage under such subscriptions.

ARR resulting from the annualization of recurring contracts with consumption measurement durations of less than one year, as a percentage of total ARR, was 50%, 47%, and 43% as of December 31, 2024, 2023, and 2022, respectively, with our E365 subscription offering representing 45%, 41%, and 35% of total ARR as of December 31, 2024, 2023, and 2022, respectively.

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In March 2022, in response to the Russia‑Ukraine war, we announced a pause of sales in Russia and Belarus, in addition to our strict compliance with applicable sanctions, regimes, and other regulatory restrictions on business activities in those countries. As a result of the conflict, we deemed our overall business recurrence in the affected countries to have been reduced by approximately 50%, and accordingly, reduced our related ARR by $5,190 as of March 31, 2022. During the second quarter of 2022, the marked shifts in the Russian business environment and economic outlook led us to conclude it was no longer viable for us to continue operations in Russia. Accordingly, we made the decision to wind down business and exit the Russian market, which resulted in a further reduction in our ARR by $6,000.

Constant currency ARR growth rate is the growth rate of ARR measured on a constant currency basis. In reporting period-over-period ARR growth rates in constant currency, we calculate constant currency growth rates by translating current and prior period ARR on a transactional basis to our reporting currency using current year budget exchange rates. We believe that ARR growth is an important metric indicating the scale and growth of our business.

Our ARR growth rate was favorably impacted by the ARR onboarding from our platform acquisition of PLS by 2.5% for the year ended December 31, 2022.

Last Twelve‑Months Recurring Revenues

Last twelve‑month recurring revenues is a key business metric that we believe is useful in evaluating our ability to consistently retain and grow our recurring revenues. We believe that we will continue to experience favorable growth in recurring revenues primarily due to our strong account retention and recurring revenues dollar‑based net retention rates, as well as the addition of new accounts with recurring revenues.

Last twelve‑months recurring revenues is calculated as recurring revenues recognized over the preceding twelve‑month period.

The last twelve‑months recurring revenues for the periods ended December 31, 2024, 2023, and 2022 compared to the last twelve‑months of the comparative twelve‑month period increased by $141,327, $118,653, and $143,874, respectively. This increase was primarily due to growth in ARR, which is primarily the result of growing our recurring revenues within our existing accounts as expressed in our recurring revenues dollar‑based net retention rate, as well as additional recurring revenues resulting from new accounts and acquisitions, including the favorable impact from our platform acquisitions of PLS and Seequent. For the twelve months ended December 31, 2024, 2023, and 2022, 91%, 89%, and 89%, respectively, of our revenues were recurring revenues.

Account Retention Rate

Account retention rate is a key business metric that we believe is useful in evaluating the long‑term value of our account relationships and our ability to retain our account base. We believe that our consistent and high account retention rates illustrate our ability to retain and cultivate long‑term relationships with our accounts.

Account retention rate for any given twelve-month period is calculated using the average foreign currency exchange rates for the prior period, as follows: the prior period recurring revenues from all accounts with recurring revenues in the current and prior period, divided by total recurring revenues from all accounts during the prior period.

Recurring Revenues Dollar‑Based Net Retention Rate

Recurring revenues dollar‑based net retention rate is a key business metric that we believe is useful in evaluating our ability to consistently retain and grow our recurring revenues.

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Recurring revenues dollar‑based net retention rate is calculated, using the average exchange rates for the prior period, as follows: the recurring revenues for the current period, including any growth or reductions from existing accounts, but excluding recurring revenues from any new accounts added during the current period, divided by the total recurring revenues from all accounts during the prior period. A period is defined as any trailing twelve months. Related to our platform acquisitions, recurring revenues into new accounts will be captured as existing accounts starting with the second anniversary of the acquisition when such data conforms to the calculation methodology. This may cause variability in the comparison.

Given that recurring revenues represented 91%, 89%, and 89% of our total revenues for the twelve months ended December 31, 2024, 2023, and 2022, respectively, this metric helps explain our revenue performance as primarily growth from existing accounts.

Non-GAAP Financial Measures:

In addition to our results determined in accordance with GAAP discussed above, we believe the following presentation of financial measures not in accordance with GAAP provides useful information to investors regarding our results of operations. To the extent material, we disclose below the additional purposes, if any, for which our management uses these non‑GAAP financial measures and provide reconciliations between these non‑GAAP financial measures and their most directly comparable GAAP financial measures. Non‑GAAP financial information should be considered in addition to, not as a substitute for, or in isolation from, the financial information prepared in accordance with GAAP, including operating income, or other measures of performance. Our non‑GAAP financial measures may vary significantly from period to period for reasons unrelated to our operating performance and may differ from similarly titled measures presented by other companies.

Adjusted OI w/SBC

Adjusted OI w/SBC is a non-GAAP financial measure and is used to measure the operational strength and performance of our business, as well as to assist in the evaluation of underlying trends in our business.

Adjusted OI w/SBC is our primary performance measure, which excludes certain expenses and charges, including the non-cash amortization expense resulting from the acquisition of intangible assets, as we believe these may not be indicative of our core business operating results. We intentionally include stock-based compensation expense in this measure as we believe it better captures the economic costs of our business.

Management uses this non-GAAP financial measure to understand and compare operating results across accounting periods, for internal budgeting and forecasting purposes, to evaluate financial performance, and in our comparison of our financial results to those of other companies. It is also a significant performance measure in certain of our executive incentive compensation programs.

Adjusted OI w/SBC is defined as operating income adjusted for the following: amortization of purchased intangibles, expense (income) relating to deferred compensation plan liabilities, acquisition expenses, and realignment expenses (income), for the respective periods.

Adjusted Operating Income

Adjusted operating income is a non-GAAP financial measure that we believe is useful to investors in making comparisons to other companies, although this measure may not be directly comparable to similar measures used by other companies.

Adjusted operating income is defined as operating income adjusted for the following: amortization of purchased intangibles, expense (income) relating to deferred compensation plan liabilities, acquisition expenses, realignment expenses (income), and stock‑based compensation expense, for the respective periods.

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Reconciliation of operating income to Adjusted OI w/SBC and to Adjusted operating income:

Year Ended December 31,
202420232022
Operating income$302,150$230,542$208,612
Amortization of purchased intangibles (1)46,67951,21953,592
Deferred compensation plan (2)12,38213,580(15,782)
Acquisition expenses (3)10,22217,86625,398
Realignment expenses (4)78911,4702,109
Adjusted OI w/SBC372,222324,677273,929
Stock-based compensation expense (5)73,50571,47074,566
Adjusted operating income$445,727$396,147$348,495

Further explanation of certain of our adjustments in arriving at Adjusted OI w/SBC and Adjusted operating income are as follows:

(1)Amortization of purchased intangibles. Amortization of purchased intangibles varies in amount and frequency and is significantly impacted by the timing and size of our acquisitions. Management finds it useful to exclude these non‑cash charges from our operating expenses to assist in budgeting, planning, and forecasting future periods. The use of intangible assets contributed to our revenues earned during the periods presented and will also contribute to our revenues in future periods. Amortization of purchased intangible assets will recur in future periods.

(2)Deferred compensation plan. We exclude Deferred compensation plan expense (income) when we evaluate our continuing operational performance because it is not reflective of our ongoing business and results of operation. We believe it is useful for investors to understand the effects of this item on our total operating expenses. Deferred compensation plan liabilities are marked to market at the end of each reporting period, with changes in the liabilities recorded as an expense (income) to Deferred compensation plan in the consolidated statements of operations.

(3)Acquisition expenses. We incur expenses for professional services rendered in connection with business combinations, which are included in our GAAP presentation of general and administrative expense. Also included in our acquisition expenses are retention incentives paid to executives of the acquired companies. We exclude these acquisition expenses when we evaluate our continuing operational performance as we would not have otherwise incurred these expenses in the periods presented as part of our continuing operations. For the year ended December 31, 2022, $9,804 of our acquisition expenses related to our platform acquisition of PLS.

(4)Realignment expenses. We exclude these charges and subsequent adjustments to our estimates when we evaluate our continuing operational performance because they are not reflective of our ongoing business and results of operations. We believe it is useful for investors to understand the effects of these items on our total operating expenses. During the fourth quarter of 2023, we approved the 2023 Program. For the years ended December 31, 2024 and 2023, we recognized realignment costs related to the aforementioned program of $847 and $12,579, respectively, which represent termination benefits for colleagues whose roles were impacted (see Note 21 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K). For the year ended December 31, 2023, Realignment expenses were partially offset by income associated with the continued wind down of our Russian entities. For the year ended December 31, 2022, Realignment expenses were comprised of asset impairments and termination benefits as a result of our decision to wind down business and exit the Russian market beginning in the second quarter of 2022.

(5)Stock‑based compensation expense. We exclude non-cash stock‑based compensation expenses from certain of our non‑GAAP measures because we believe this is useful to investors in making comparisons to other companies.

Constant Currency

Constant currency and constant currency growth rates are non-GAAP financial measures that present our results of operations excluding the estimated effects of foreign currency exchange rate fluctuations. A significant amount of our operations is conducted in foreign currencies. As a result, the comparability of the financial results reported in U.S. dollars is affected by changes in foreign currency exchange rates. We use constant currency and constant currency growth rates to evaluate the underlying performance of the business, and we believe it is helpful for investors to present operating results on a comparable basis period over period to evaluate its underlying performance.

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In reporting period‑over‑period results, except for ARR as discussed above in “Key Business Metrics” section, we calculate the effects of foreign currency fluctuations and constant currency information by translating current and prior period results on a transactional basis to our reporting currency using prior period average foreign currency exchange rates in which the transactions occurred.

Reconciliation of consolidated revenues to consolidated revenues in constant currency:

Constant Currency Change 2023 to 2024:

Year Ended December 31, 2024Year Ended December 31, 2023
ActualImpact of Foreign Exchange at 2023 RatesConstant CurrencyActualImpact of Foreign Exchange at 2023 RatesConstant Currency
Subscriptions$1,223,362$814$1,224,176$1,080,307$(977)$1,079,330
Perpetual licenses45,96132346,28446,038(4)46,034
Subscriptions and licenses1,269,3231,1371,270,4601,126,345(981)1,125,364
Services83,772(291)83,481102,068(61)102,007
Total revenues$1,353,095$846$1,353,941$1,228,413$(1,042)$1,227,371

Constant Currency Change 2022 to 2023:

Year Ended December 31, 2023Year Ended December 31, 2022
ActualImpact of Foreign Exchange at 2022 RatesConstant CurrencyActualImpact of Foreign Exchange at 2022 RatesConstant Currency
Subscriptions$1,080,307$1,239$1,081,546$960,220$809$961,029
Perpetual licenses46,03856346,60143,3774343,420
Subscriptions and licenses1,126,3451,8021,128,1471,003,5978521,004,449
Services102,068684102,75295,48512995,614
Total revenues$1,228,413$2,486$1,230,899$1,099,082$981$1,100,063

Reconciliation of revenues by geographic region to revenues by geographic region in constant currency:

Constant Currency Change 2023 to 2024:

Year Ended December 31, 2024Year Ended December 31, 2023
ActualImpact of Foreign Exchange at 2023 RatesConstant CurrencyActualImpact of Foreign Exchange at 2023 RatesConstant Currency
Americas$717,002$1,751$718,753$650,926$(238)$650,688
EMEA388,384(2,754)385,630353,550(118)353,432
APAC247,7091,849249,558223,937(686)223,251
Total revenues$1,353,095$846$1,353,941$1,228,413$(1,042)$1,227,371

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Constant Currency Change 2022 to 2023:

Year Ended December 31, 2023Year Ended December 31, 2022
ActualImpact of Foreign Exchange at 2022 RatesConstant CurrencyActualImpact of Foreign Exchange at 2022 RatesConstant Currency
Americas$650,926$242$651,168$584,794$(313)$584,481
EMEA353,550(2,841)350,709312,804151312,955
APAC223,9375,085229,022201,4841,143202,627
Total revenues$1,228,413$2,486$1,230,899$1,099,082$981$1,100,063

Reconciliation of cost of revenues to cost of revenues in constant currency:

Constant Currency Change 2023 to 2024:

Year Ended December 31, 2024Year Ended December 31, 2023
ActualImpact of Foreign Exchange at 2023 RatesConstant CurrencyActualImpact of Foreign Exchange at 2023 RatesConstant Currency
Cost of subscriptions and licenses$173,340$140$173,480$169,406$22$169,428
Cost of services84,427(101)84,32696,677696,683
Total cost of revenues$257,767$39$257,806$266,083$28$266,111

Constant Currency Change 2022 to 2023:

Year Ended December 31, 2023Year Ended December 31, 2022
ActualImpact of Foreign Exchange at 2022 RatesConstant CurrencyActualImpact of Foreign Exchange at 2022 RatesConstant Currency
Cost of subscriptions and licenses$169,406$382$169,788$147,578$(45)$147,533
Cost of services96,67777297,44989,435(53)89,382
Total cost of revenues$266,083$1,154$267,237$237,013$(98)$236,915

Reconciliation of operating expenses to operating expenses in constant currency:

Constant Currency Change 2023 to 2024:

Year Ended December 31, 2024Year Ended December 31, 2023
ActualImpact of Foreign Exchange at 2023 RatesConstant CurrencyActualImpact of Foreign Exchange at 2023 RatesConstant Currency
Research and development$281,247$817$282,064$274,619$17$274,636
Selling and marketing255,177505255,682224,336(212)224,124
General and administrative210,374(106)210,268180,738(308)180,430
Deferred compensation plan12,38212,38213,58013,580
Amortization of purchased intangibles33,998(39)33,95938,515(2)38,513
Total operating expenses$793,178$1,177$794,355$731,788$(505)$731,283

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Constant Currency Change 2022 to 2023:

Year Ended December 31, 2023Year Ended December 31, 2022
ActualImpact of Foreign Exchange at 2022 RatesConstant CurrencyActualImpact of Foreign Exchange at 2022 RatesConstant Currency
Research and development$274,619$2,592$277,211$257,856$(36)$257,820
Selling and marketing224,336427224,763195,622(48)195,574
General and administrative180,738182180,920174,647(6)174,641
Deferred compensation plan13,58013,580(15,782)(15,782)
Amortization of purchased intangibles38,5158838,60341,1146841,182
Total operating expenses$731,788$3,289$735,077$653,457$(22)$653,435

Liquidity and Capital Resources:

Cash and Cash Equivalents

December 31,
20242023
Cash and cash equivalents held domestically$2,845$3,693
Cash and cash equivalents held by foreign subsidiaries61,16464,719
Total cash and cash equivalents$64,009$68,412

Our primary source of operating cash is from the sale of our subscriptions, perpetual licenses, and services. Our primary use of cash is payment of our operating costs, which consist mainly of headcount‑related costs. In addition to operating expenses, we also use cash to service our debt obligations, to pay quarterly dividends, to repurchase our Class B common stock and convertible debt, and for capital expenditures in support of our operations. We also use cash to fund our acquisitions of software assets and businesses, and other investment activities.

During the years ended December 31, 2024 and 2023, we made cash repatriations to the U.S. of approximately $138,000 and $93,000, respectively, from earnings generated by our foreign subsidiaries. In 2024 and 2023, the repatriations were primarily used to pay down our credit facility borrowings and to supplement our domestic working capital needs.

We believe that cash generated from operations, together with existing cash and cash equivalent balances, and external borrowings including available liquidity under the Credit Facility, will be sufficient to meet our domestic and international working capital and capital expenditure requirements. We regularly review our capital structure and consider a variety of potential financing alternatives and planning strategies to ensure that we have the proper liquidity available in the locations in which it is needed and to fund our operations and growth investments with cash that has not been permanently reinvested outside the U.S. Our future capital requirements may be materially different than those currently planned in our budgeting and forecasting activities and depend on many factors, including our strategy of regularly acquiring and integrating specialized infrastructure engineering software businesses, our rate of revenue growth, the timing and extent of spending on research and development, the expansion of our sales and marketing activities, the timing of new product introductions, market acceptance of our products, competitive factors, our discretionary payments of dividends or repurchases of our Class B common stock and convertible debt, funding of our purchase commitments, currency fluctuations, and overall economic conditions, globally. To the extent that current and anticipated future sources of liquidity are insufficient to fund our future business activities and requirements, we may be required to seek additional equity or debt financing. The sale of additional equity would result in additional dilution to our stockholders, while the incurrence of additional debt financing, including convertible debt, would result in additional debt service obligations. Such debt instruments also could introduce new or modified covenants that might restrict our operations and/or our ability to pay dividends,

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consummate acquisitions, or otherwise pursue our business strategies. We cannot provide assurance that we could obtain additional financing on favorable terms or at all.

Cash Flows Activity

Year Ended December 31,
202420232022
Net cash provided by (used in):
Operating activities$435,292$416,696$274,324
Investing activities(143,267)(60,504)(770,127)
Financing activities(289,850)(359,074)243,034

Operating Activities

For the year ended December 31, 2024, compared to the prior year, net cash provided by operating activities was higher by $18,596 due to a net increase in non‑cash adjustments of $185,856, partially offset by a decrease in net income of $92,354 and a decrease in net cash flows from the change in operating assets and liabilities of $74,906. Both the decrease in net income and the net increase in non‑cash adjustments were impacted by the fourth quarter of 2023 internal legal entity restructuring and related intra-entity transactions as part of our continuing efforts to align intellectual property ownership with our business operating model. The net impact of the internal legal entity restructuring was a net discrete tax benefit of $170,784 for the year ended December 31, 2023. See Note 16 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information. The decrease in net cash flows from the change in operating assets and liabilities was primarily due to the timing of collections on our receivables, the overall timing of tax payments year over year, and a decrease in deferred revenues.

Investing Activities

Net cash used in investing activities was higher by $82,763 for the year ended December 31, 2024, compared to the prior year, primarily due to higher acquisition related payments of $104,384, partially offset by lower purchases of property and equipment and investment in capitalized software of $10,956 and lower purchases of investments of $10,167. We used available cash and borrowings under our 2017 Credit Facility to fund an acquisition in September 2024.

Financing Activities

Net cash used in financing activities was lower by $69,224 for the year ended December 31, 2024, compared to the prior year, primarily due to lower net paydowns of the credit facilities of $111,856, partially offset by higher payments for shares acquired of $17,926, including shares repurchased under the BSY Stock Repurchase Program (the “Repurchase Program”), and higher dividend payments of $13,359, primarily due to an increase in our quarterly dividend per share to $0.06 in 2024 from $0.05 in 2023.

Long-Term Debt

December 31,
20242023
Current portion of long-term debt$$10,000
Long-term debt1,388,0881,518,403
Total debt$1,388,088$1,528,403

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On October 18, 2024, we entered into the Credit Facility, which provides us with a $1,300,000 revolving credit facility, including a $125,000 swingline loan and $125,000 in letters of credit. The Credit Facility also provides us with a $500,000 “accordion” feature to increase the facility in the form of both revolving indebtedness and/or incremental term loans. On October 18, 2024, we used borrowings under the Credit Facility to repay all indebtedness outstanding under the 2017 Credit Facility, including the outstanding senior secured term loan.

As of December 31, 2024, we had $1,164,535 available under the Credit Facility, and we were in compliance with all covenants under the Credit Facility, the 2026 Notes, and the 2027 Notes. Any failure to comply with such covenants under the Credit Facility would prevent us from being able to borrow additional funds under the Credit Facility, and, as with any failure to comply with such covenants under the 2026 Notes and the 2027 Notes, could constitute a default that may cause all amounts outstanding to become due and immediately payable in full.

Our credit facilities, 2026 Notes, and 2027 Notes are described in Note 10 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K.

Stock Repurchases

BSY Stock Repurchase Program

Our Board of Directors had authorized us to repurchase up to $200,000 of our Class B common stock and/or outstanding convertible senior notes through June 30, 2024 under the Repurchase Program. This authorization under the Repurchase Program expired on June 30, 2024. In March 2024, our Board of Directors approved an extension to the Repurchase Program authorizing us to repurchase up to $200,000 of our Class B common stock and/or outstanding convertible senior notes from June 30, 2024 through June 30, 2026. We may use available working capital, cash provided by operating activities, and/or external borrowings including available liquidity under our Credit Facility to make repurchases.

During the year ended December 31, 2024, we repurchased 1,292,733 shares for $64,359 under the Repurchase Program. During the year ended December 31, 2023, we did not make repurchases under the Repurchase Program.

The timing, as well as the number and value of shares and/or outstanding convertible senior notes repurchased under the Repurchase Program, will be determined at our discretion and will depend on a variety of factors, including our assessment of the intrinsic value of our shares, the market price of our Class B common stock and outstanding convertible senior notes, general market and economic conditions, available liquidity, compliance with our debt and other agreements, and applicable legal requirements.

Withholding Taxes on Certain Equity Awards

We have the right to require that certain equity awardees receive gross or net quantities of shares of our Class B common stock, including distributions from the DCP and share issuances under the amended and restated Bentley Systems, Incorporated Bonus Pool Plan (the “Bonus Plan”). In the case of a gross issuance or distribution, an awardee is required to reimburse promptly to us the cash required for his or her tax withholding amounts. Conversely, under a net issuance or distribution, shares are withheld in consideration of remitting withholding taxes on behalf of an equity awardee, thereby requiring us to remit cash for the tax withholdings. During the year ended December 31, 2024, we exercised our right to require that impacted equity awardees receive gross quantities of our Class B common stock. During the year ended December 31, 2023, we allowed impacted equity awardees the option to receive net quantities of shares of our Class B common stock during the first, second, and third quarters, but exercised our right to require that these awardees receive gross quantities of our Class B common stock during the fourth quarter. We will continue to evaluate whether share awards will be required to be received by awardees on a gross basis, or if net settlement may be elected by awardees.

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Dividend Payments

The declaration and payment of dividends is within the discretion of our Board of Directors. We paid quarterly dividends of $0.06 per share of common stock during the year ended December 31, 2024 and $0.05 per share of common stock during the year ended December 31, 2023. While we intend to continue paying quarterly dividends, any future determination will be subject to the discretion of our Board of Directors and will be dependent on a number of factors, including our results of operations, capital requirements, restrictions under Delaware law, and overall financial condition, as well as any other factors our Board of Directors considers relevant. In addition, the terms of the agreement governing the Credit Facility limit the amount of dividends we can pay.

Contractual Obligations and Other Commitments:

The following table summarizes our most significant contractual obligations as of December 31, 2024:

TotalShort-TermLong-Term
Debt Obligations (1)$1,398,145$$1,398,145
Purchase Obligations113,70059,20054,500
DCP Obligations100,4823,79896,684

(1)Amounts represent the face value of debt and exclude interest payments.

Our largest contractual obligations relate to our outstanding debt, which include convertible notes due in 2026 and 2027. Our Credit Facility matures on October 18, 2029, subject to a “revolving maturity date” on the date that is 91 days prior to the maturity date of our outstanding convertible debt, unless on such date we meet certain liquidity requirements. We typically fund and expect to continue to fund debt maturities and interest payments with cash flows generated from operations, existing cash and cash equivalents, or proceeds from additional financing. If an early conversion notice is received, we have the option to pay cash, deliver shares of our Class B common stock, or a combination thereof. See Note 10 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our debt obligations.

We have non‑cancelable future cash purchase commitments for services related to cloud provisioning of our software solutions and for internal‑use software costs. Our purchase obligations are in addition to amounts included in our consolidated balance sheets. We have funded and expect to continue to be able to fund our purchase obligations with cash flows generated from operations, existing cash and cash equivalents or revolving loan borrowings under the Credit Facility. See Note 18 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our purchase obligations.

Our DCP obligations represent DCP participants’ holdings in phantom investment funds, which are classified as liabilities as they will be settled in cash upon eventual distribution. We have funded and expect to continue to be able to fund our DCP obligations with cash flows generated from operations, existing cash and cash equivalents, or revolving loan borrowings under the Credit Facility. See Note 12 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our DCP obligations.

Our other future contractual obligations are related to leases. See Note 8 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our lease obligations.

Critical Accounting Estimates:

The preparation of our consolidated financial statements in conformity with GAAP requires us to make estimates that affect the reported amounts of assets, liabilities, revenue and expenses, and the related disclosure of contingent assets and contingent liabilities. We base our judgments on our historical experience and on various other assumptions that we believe are reasonable under the circumstances, the results of which form the basis for making estimates about the carrying value of assets and liabilities that are not readily apparent from other sources. Actual results may differ from these estimates under different assumptions or conditions.

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Revenue Recognition

Our contracts with customers may include promises to transfer licenses (perpetual or term‑based), maintenance, and services to a user. Judgment is required to determine if the promises are separate performance obligations, and if so, the allocation of the transaction price to each performance obligation. When an arrangement includes multiple performance obligations which are concurrently delivered and have the same pattern of transfer to the customer, we account for those performance obligations as a single performance obligation. For contracts with more than one performance obligation, the transaction price is allocated among the performance obligations in an amount that depicts the relative standalone selling price (“SSP”) of each obligation. Judgment is required to determine the SSP for each distinct performance obligation. In instances where SSP is not directly observable, such as when we do not sell the product or service separately, we determine the SSP using information that may include market conditions and other observable inputs. We use a range of amounts to estimate SSP when we sell each of the products and services separately and need to determine whether there is a discount that should be allocated based on the relative SSP of the various products and services.

Our SELECT agreement provides users with perpetual licenses a right to exchange software for other eligible perpetual licenses on an annual basis upon renewal. We refer to this option as portfolio balancing and concluded that the portfolio balancing feature represents a material right resulting in the deferral of the associated revenue. Judgment is required to estimate the percentage of users who may elect to portfolio balance and considers inputs such as historical user elections. This feature is available once per term and must be exercised prior to the respective renewal term. We recognize the associated revenue upon election or when the portfolio balancing right expires. This right is included in the initial and subsequent renewal terms and we reestablish the revenue deferral for the material right upon the beginning of the renewal term. Portfolio balancing exchange rights are included in Deferred revenues in the consolidated balance sheets.

Goodwill and Other Intangible Assets

Intangible assets arise from acquisitions and principally consist of goodwill, trademarks, customer relationships, in‑process research and development, and acquired software and technology. Intangible assets, other than goodwill and in‑process research and development, are amortized on a straight‑line basis over their estimated useful lives.

Goodwill

Goodwill consists of the excess of cost over the fair value of net assets acquired in business combinations. Goodwill is not amortized but instead is tested annually for impairment on October 1, or more frequently if events occur or circumstances change that would more likely than not reduce its fair value below its carrying amount. We allocate goodwill to reporting units on a relative fair value basis.

In testing for goodwill impairment, we may first qualitatively assess whether it is more likely than not (a likelihood of more than 50 percent) that a goodwill impairment exists. If it is determined that a quantitative assessment is required and the carrying amount exceeds its fair value, we will recognize goodwill impairment in the amount in which the carrying amount of the reporting unit exceeds its fair value, but not to exceed the carrying amount of goodwill within the reporting unit. The process of evaluating the potential impairment of goodwill is subjective and requires significant judgment at many points in the process. The value of our goodwill could also be impacted by future adverse changes including declines in our stock price, market capitalization, or cash flows, and slower growth rates in our industry. There was no impairment of goodwill as a result of our annual impairment assessments conducted for the years ended December 31, 2024, 2023, or 2022.

Other Intangible Assets

Intangible assets other than goodwill are tested annually for impairment on October 1, or more frequently if events occur or circumstances change that would more likely than not reduce its fair value below its carrying amount.

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In testing intangible assets other than goodwill for impairment, we may first qualitatively assess whether it is more likely than not (a likelihood of more than 50 percent) that an intangible asset impairment exists. If it is determined that a quantitative assessment is required, we will evaluate the cash flows generated by the underlying asset, including estimated future operation results, trends, or other determinants of fair value. If the total of the expected future undiscounted cash flows were less than the carrying amount of the asset, we would recognize an impairment charge to the extent the carrying amount of the asset exceeded its estimated fair value. There was no impairment of intangible assets for the years ended December 31, 2024, 2023, or 2022.

Income Taxes

We account for income taxes under the asset and liability method, which requires the recognition of deferred tax assets and liabilities for the expected future tax consequences of events that have been included in the consolidated financial statements. Under this method, deferred tax assets and liabilities are determined based on net operating loss (“NOL”) carryforwards, credit carryforwards, and temporary differences between the financial statement and tax basis of assets and liabilities using enacted tax rates in effect for the year in which the items are expected to reverse. The effect of a change in tax rates on deferred tax assets and liabilities is recognized in income in the period of the enactment date.

We perform a quarterly assessment of the recoverability of the net deferred tax assets. We consider all available evidence, both positive and negative, in determining whether all or a portion of a deferred tax asset is more likely than not to be realized. In the event we determine that all or a portion of the deferred tax assets is not more likely than not to be realized, an adjustment to the valuation allowance would be recorded that would increase the provision for income taxes. To the extent that the realization of a deferred tax asset is based upon forecasted future earnings, our judgment regarding future profitability may change due to future market conditions and other factors. Assumptions about future taxable income require significant judgment and, while these assumptions rely heavily on estimates, such estimates are consistent with the plans we are using to manage the underlying business. Any change in future profitability may require material adjustments to these net deferred tax assets, resulting in a reduction in net income in the period when such determination is made. Additionally, future changes in tax laws and rates, including administrative or regulatory guidance, could affect recorded deferred tax assets and liabilities. Any adjustments to these estimates will generally be recorded as an income tax expense or benefit in the period the adjustment is determined.

We are subject to income taxes in the U.S. and in numerous foreign jurisdictions. The calculation of our tax liabilities often involves dealing with uncertainties in the application of complex tax laws and regulations in a multitude of jurisdictions across our global operations. There are many transactions and calculations about which the ultimate tax outcome is uncertain. A benefit from an uncertain tax position may be recognized when it is more likely than not that the position will be sustained based upon the technical merits of the position. This may include expected resolutions upon examination, any related appeals, or through a litigation processes. As a result, our calculations involve estimates by management. Due to the complexity of some of these uncertainties, the ultimate resolution may result in a payment, potentially including interest and penalties, that is materially different from our current estimates of the unrecognized tax benefit liabilities. These differences, along with any related interest and penalties, will generally be reflected as increases or decreases to income tax expense in the period in which new information becomes available. We review the tax reserves as circumstances warrant and adjust the reserves as events occur that affect our potential liability for additional taxes. We follow the applicable guidance on derecognition, classification, interest and penalties, accounting in interim periods, disclosure, and transition with respect to uncertain tax positions. We recognize interest and penalties related to income taxes within the (Provision) benefit for income taxes line in the consolidated statements of operations. Accrued interest and penalties are included within the related tax liability line in the consolidated balance sheets.

FY 2023 10-K MD&A

SEC filing source: 0001031308-24-000002.

Extracted structurally from real Item 7 body heading to real Item 7A/8 boundary. Confidence: high. Filing date: 2024-02-27. Report date: 2023-12-31.

Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations

The following discussion should be read in conjunction with our audited consolidated financial statements and notes thereto included in Part II, Item 8 of this Annual Report on Form 10‑K. In addition to historical information, this discussion contains forward‑looking statements that involve risks, uncertainties, and assumptions that could cause actual results to differ materially from management’s expectations. Factors that could cause such differences are set forth in Part I, Item 1A. Risk Factors of this Annual Report on Form 10‑K. Refer to Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations in our 2022 Annual Report on Form 10‑K for management’s discussion and analysis of financial condition and results of operations for the year ended December 31, 2022 compared to the year ended December 31, 2021.

During the fourth quarter of 2023, we changed our definitions of constant currency and constant currency growth rates. In reporting period‑over‑period results, we calculate the effects of foreign currency fluctuations and constant currency information by translating current period results on a transactional basis to our reporting currency using prior period average foreign currency exchange rates in which the transactions occurred. Our prior definition of constant currency calculated the effects of foreign currency fluctuations and constant currency information by translating current period results of our subsidiaries from their functional currencies to our reporting currency by using prior period average foreign currency exchange rates in reporting period‑over‑period results.

Prior period amounts have been revised to conform to the current period presentation using the updated constant currency and constant currency growth rates definitions. We are providing what our constant currency and constant currency growth rates results would have been pursuant to the prior definition for the applicable periods so that investors and potential investors that have analyzed these non-GAAP financial measures historically using our prior definitions can compare our historical results to our current results with respect to these non-GAAP financial measures using the prior definitions. Refer to the section titled “Non‑GAAP Financial measures” for reconciliations of constant currency non‑GAAP financial measures and their most directly comparable GAAP financial measures under the current and prior definitions.

All amounts presented in this Management’s Discussion and Analysis of Financial Condition and Results of Operations, except share and per share amounts, are presented in thousands. Additionally, many of the amounts and percentages have been rounded for convenience of presentation. Minor differences in totals and percentage calculations may exist due to rounding.

Overview:

Bentley Systems is the infrastructure engineering software company. Our purpose is to advance the world’s infrastructure for better quality of life. We empower people to design, build, and operate better and more resilient infrastructure through the adoption of our intelligent digital twin solutions. We manage our business globally within one reportable segment, the development and marketing of computer software and related services, which is consistent with how our chief operating decision maker (“CODM”) reviews and manages our business.

Executive Summary:

•Total revenues were $1,228,413 for the year ended December 31, 2023, up 11.8% or 11.9% on a constant currency basis(1) compared to the prior year;

•Subscriptions revenues were $1,080,307 for the year ended December 31, 2023, up 12.5% or 12.5% on a constant currency basis(1) compared to the prior year;

•ARR(2) was $1,174,774 as of December 31, 2023, compared to $1,036,548 as of December 31, 2022, representing a constant currency ARR growth rate(2) of 12.5%;

•Last twelve-month recurring revenues dollar-based net retention rate(2) was 109% as of the year ended December 31, 2023, compared to 110% as of December 31, 2022;

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•Operating income was $230,542 for the year ended December 31, 2023, compared to $208,612 for the prior year;

•Adjusted operating income inclusive of stock-based compensation expense (“Adjusted OI w/SBC”)(1) was $324,677 for the year ended December 31, 2023, compared to $273,929 for the prior year; and

•Cash flow from operations was $416,696 for the year ended December 31, 2023, compared to $274,324 for the prior year.

(1)Constant currency and Adjusted OI w/SBC are non‑GAAP financial measures. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our definitions and our uses of constant currency and Adjusted OI w/SBC.

(2)Refer to the “Key Business Metrics” section for additional information, including our definitions and our uses of ARR, ARR growth rate, and recurring revenues dollar-based net retention rate.

(3)Adjusted OI w/SBC is a non‑GAAP financial measure. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our definition and our use of Adjusted OI w/SBC.

Results of Operations:

Impact of Foreign Currency

Our results of operations have been, and in the future will be, affected by changes in foreign currency exchange rates. For the years ended December 31, 2023, 2022, and 2021, approximately 35%, 36%, and 47%, respectively, of our total revenues and 45%, 46%, and 42%, respectively, of our total operating expenses were denominated in foreign currencies from outside the U.S. including most significantly: euros, British pounds, Canadian dollars, Australian dollars, Chinese yuan renminbi, and New Zealand dollars. Other than the natural hedge attributable to matching revenues and expenses in the same currencies, we do not currently hedge foreign currency exposure.

We identify the effects of foreign currency on our operations and present constant currency growth rates and fluctuations because we believe exchange rates are an important factor in understanding period‑over‑period comparisons and enhance the understanding of our results and evaluation of our performance. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our definition and our use of constant currency.

Revenues

We generate revenues from subscriptions, perpetual licenses, and services. Our total revenues are diversified by account type, size, and geography. Our sources of revenue growth, excluding the impact from acquisitions, come from additional subscriptions revenues from existing accounts using the same products and represent the majority of our revenue growth, additional subscriptions revenues from existing accounts using new products, and subscriptions revenues from new accounts. We believe that we have a loyal account base, with over 70% of our total revenues for the years ended December 31, 2023, 2022, and 2021 generated from organizations that have been our accounts for over ten years.

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In addition to our results of operations discussed below, the following is supplemental data of our revenues:

Year Ended December 31,
(as a percentage of total revenues)202320222021
Revenues from:
Direct sales channels92%92%92%
Indirect channel partners8%8%8%
Revenues from:
Subscriptions88%87%84%
Recurring services1%2%2%
Total recurring revenues89%89%86%
Perpetual licenses and other services11%11%14%
Largest account represents no more than2.0%2.0%2.5%

The volume, mix, and duration of contract types starting or renewing in any given period may have a material impact on revenue in the period, and as a result can impact the comparability of reported revenue period-over-period. Our subscriptions, perpetual licenses, and services offerings are recognized pursuant to applicable GAAP guidance. See Note 3 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our revenues. We believe that subscription revenues will continue to comprise a majority of our total revenues.

Consolidated Revenues

Current Definition of Constant Currency:

% Change% Change
2022 to 20232021 to 2022
ConstantConstant
Year Ended December 31,CurrencyCurrency
202320222021%%(1)%%(1)
Subscriptions$1,080,307$960,220$812,80712.5%12.5%18.1%22.0%
Perpetual licenses46,03843,37753,0806.1%7.3%(18.3%)(14.1%)
Subscriptions and licenses1,126,3451,003,597865,88712.2%12.3%15.9%19.8%
Services102,06895,48599,1596.9%7.5%(3.7%)(0.1%)
Total revenues$1,228,413$1,099,082$965,04611.8%11.9%13.9%17.7%

(1)Constant currency is a non‑GAAP financial measure. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our current definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

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Prior Definition of Constant Currency:

% Change% Change
2022 to 20232021 to 2022
ConstantConstant
Year Ended December 31,CurrencyCurrency
202320222021%%(1)%%(1)
Subscriptions$1,080,307$960,220$812,80712.5%11.7%18.1%24.3%
Perpetual licenses46,03843,37753,0806.1%5.9%(18.3%)(12.1%)
Subscriptions and licenses1,126,3451,003,597865,88712.2%11.4%15.9%22.1%
Services102,06895,48599,1596.9%7.5%(3.7%)0.4%
Total revenues$1,228,413$1,099,082$965,04611.8%11.1%13.9%19.8%

(1)Constant currency is a non‑GAAP financial measure. Refer to the “Non‑GAAP Financial Measures” section for additional information, including our prior definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

The increase in total revenues for the year ended December 31, 2023 was primarily driven by increases in subscriptions revenues, and to a lesser extent, services and perpetual licenses revenues.

Subscriptions. For the year ended December 31, 2023, the increase in subscriptions revenues was primarily driven by improvements in our business performance of approximately $115,786 ($116,406 on a constant currency basis) and the impact of our platform acquisition of approximately $4,301 ($4,111 on a constant currency basis). Our business performance excludes the impact of our platform acquisitions and includes the impact from programmatic acquisitions, which generally are immaterial, individually and in the aggregate. The platform acquisition impact relates to our acquisition of PLS and is inclusive of PLS’ organic performance.

The improvements in business performance were primarily driven by expansion from accounts with revenues in the prior period (“existing accounts”), and growth of 3% attributable to new accounts, most notably small- and medium-sized accounts. Improvements in business performance for the year ended December 31, 2023 were led by our engineering applications, geoprofessional applications, and our Bentley Infrastructure Cloud for project delivery.

Perpetual licenses. For the year ended December 31, 2023, the increase in perpetual licenses revenues was primarily driven by improvements in business performance of approximately $2,661 ($3,181 on a constant currency basis).

Services. For the year ended December 31, 2023, the increase in services revenues was primarily driven by improvements in our business performance of approximately $6,583 ($7,138 on a constant currency basis).

For the year ended December 31, 2023, the improvements in business performance were primarily driven by contributions from Cohesive digital integrator services of approximately $8,684 ($8,834 on a constant currency basis).

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Revenues by Geographic Region

Revenue from external customers is attributed to individual countries based upon the location of the customer.

Current Definition of Constant Currency:

% Change% Change
2022 to 20232021 to 2022
ConstantConstant
Year Ended December 31,CurrencyCurrency
202320222021%%(1)%%(1)
Americas$650,926$584,794$483,08711.3%11.4%21.1%21.2%
EMEA353,550312,804300,12313.0%12.1%4.2%12.9%
APAC223,937201,484181,83611.1%13.0%10.8%16.3%
Total revenues$1,228,413$1,099,082$965,04611.8%11.9%13.9%17.7%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our current definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

Prior Definition of Constant Currency:

% Change% Change
2022 to 20232021 to 2022
ConstantConstant
Year Ended December 31,CurrencyCurrency
202320222021%%(1)%%(1)
Americas$650,926$584,794$483,08711.3%11.0%21.1%22.1%
EMEA353,550312,804300,12313.0%11.1%4.2%15.4%
APAC223,937201,484181,83611.1%11.2%10.8%21.1%
Total revenues$1,228,413$1,099,082$965,04611.8%11.1%13.9%19.8%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our prior definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

Americas. For the year ended December 31, 2023, the increase in revenues from the Americas was primarily driven by improvements in our business performance of approximately $62,442 ($63,450 on a constant currency basis) and the impact from our platform acquisition of approximately $3,690 ($3,237 on a constant currency basis).

The improvements in business performance for the year ended December 31, 2023 were primarily due to expansion of our subscriptions revenues from existing accounts in the U.S.

EMEA. For the year ended December 31, 2023, the increase in revenues from EMEA was primarily driven by improvements in our business performance of approximately $40,297 ($37,345 on a constant currency basis).

The improvements in business performance for the year ended December 31, 2023 were primarily due to expansion of our subscriptions revenues from existing accounts in the United Kingdom (“U.K.”), and the Middle East and Africa, partially offset by reductions in Russia due to exiting our operations beginning in the second quarter of 2022.

APAC. For the year ended December 31, 2023, the increase in revenues from APAC was primarily driven by improvements in our business performance of approximately $22,291 ($25,930 on a constant currency basis).

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The improvements in business performance for the year ended December 31, 2023 were primarily due to expansion of our subscriptions revenues from existing accounts in India, Australia, and Southeast Asia, partially offset by declines in China.

Total revenues in China for the year ended December 31, 2023 increased as compared to the same period in the prior year, primarily due to expansion of our perpetual licenses revenues. The future results in China remain uncertain as a result of continued geopolitical challenges, the obstacles there to cloud‑deployed software, and the financial timing impact of the preference there for license sales, rather than subscriptions.

Cost of Revenues and Operating Expense (Income)

Headcount-Related Costs

For the years ended December 31, 2023, 2022, and 2021, approximately 80% of our aggregate cost of revenues, research and development, selling and marketing, and general and administrative expenses were represented by what we refer to herein as “headcount‑related” costs. These costs primarily include salaries, benefits, bonuses, stock‑based compensation expense, employment taxes, travel, training, and realignment of our colleagues, and third‑party personnel expenses and related overhead. Our headcount‑related costs are variable in nature. We actively manage these costs to align to our trending run rate of revenue performance, with the objective of enhancing visibility and predictability of resulting operating profit margins.

During the fourth quarter of 2023, the Company approved a strategic realignment program to better serve our accounts and to better align resources with the strategy of the business, including reinvestment in go-to-market functions, as well as in AI product development. The realignment program resulted in realignment costs of $12,579, which represent termination benefits for colleagues whose roles were impacted (less than five percent of total headcount). See Note 21 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information. The realignment program activities have been broadly implemented across our various businesses with the intention that substantially all actions, including payment of the termination benefits, will be fully completed by mid‑2024. The impact of the realignment program on headcount-related costs for the year ended December 31, 2023 is included in our discussion below.

Cost of Revenues

Current Definition of Constant Currency:

% Change% Change
2022 to 20232021 to 2022
ConstantConstant
Year Ended December 31,CurrencyCurrency
202320222021%%(1)%%(1)
Cost of subscriptions and licenses$169,406$147,578$124,32114.8%15.1%18.7%22.2%
Cost of services96,67789,43592,2188.1%9.0%(3.0%)2.0%
Total cost of revenues$266,083$237,013$216,53912.3%12.8%9.5%13.6%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our current definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

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Prior Definition of Constant Currency:

% Change% Change
2022 to 20232021 to 2022
ConstantConstant
Year Ended December 31,CurrencyCurrency
202320222021%%(1)%%(1)
Cost of subscriptions and licenses$169,406$147,578$124,32114.8%14.7%18.7%24.5%
Cost of services96,67789,43592,2188.1%9.0%(3.0%)2.3%
Total cost of revenues$266,083$237,013$216,53912.3%12.5%9.5%15.1%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our prior definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

Cost of subscriptions and licenses. Cost of subscriptions and licenses expenses primarily include headcount‑related costs, as well as depreciation of property and equipment and amortization of capitalized software costs associated with servicing software subscriptions, amortization of intangible assets associated with acquired software and technology, channel partner compensation for providing sales coverage to users, as well as cloud‑related costs incurred for servicing our accounts using cloud provisioned solutions and our license administration platform.

For the year ended December 31, 2023, on a constant currency basis, cost of subscriptions and licenses increased primarily due to an increase in headcount‑related costs of approximately $14,407, mainly due to an increase in headcount and annual compensation costs, and an increase in cloud‑related costs of approximately $4,949.

Cost of services. Cost of services expenses primarily include headcount‑related costs, as well as depreciation of property and equipment and amortization of capitalized software costs, used for providing training, implementation, configuration, and customization services to accounts.

For the year ended December 31, 2023, on a constant currency basis, cost of services increased primarily due to an increase in headcount‑related costs of approximately $7,991, mainly due to third‑party personnel costs, and to a lesser extent, increases in headcount and annual compensation costs, partially offset by lower acquisition-related retention incentives.

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Operating Expense (Income)

Current Definition of Constant Currency:

% Change% Change
2022 to 20232021 to 2022
ConstantConstant
Year Ended December 31,CurrencyCurrency
202320222021%%(1)%%(1)
Research and development$274,619$257,856$220,9156.5%7.5%16.7%21.8%
Selling and marketing224,336195,622162,24014.7%14.9%20.6%25.8%
General and administrative180,738174,647150,1163.5%3.6%16.3%19.1%
Deferred compensation plan13,580(15,782)95,046NMNMNMNM
Amortization of purchased intangibles38,51541,11425,601(6.3%)(6.3%)60.6%67.5%
Total operating expenses$731,788$653,457$653,91812.0%12.5%(0.1%)3.8%

Percentage changes that are considered not meaningful are denoted with NM.

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our current definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

Prior Definition of Constant Currency:

% Change% Change
2022 to 20232021 to 2022
ConstantConstant
Year Ended December 31,CurrencyCurrency
202320222021%%(1)%%(1)
Research and development$274,619$257,856$220,9156.5%7.5%16.7%22.1%
Selling and marketing224,336195,622162,24014.7%15.0%20.6%26.3%
General and administrative180,738174,647150,1163.5%3.5%16.3%19.7%
Deferred compensation plan13,580(15,782)95,046NMNMNMNM
Amortization of purchased intangibles38,51541,11425,601(6.3%)(6.1%)60.6%67.2%
Total operating expenses$731,788$653,457$653,91812.0%12.5%(0.1%)4.2%

Percentage changes that are considered not meaningful are denoted with NM.

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our prior definition and our use of constant currency, and for a reconciliation of constant currency growth rates.

Research and development. Research and development expenses primarily include headcount‑related costs, as well as costs to develop software products or the software component of products to be sold, leased, or marketed to external accounts, before technological feasibility is reached, which is generally shortly before the release of such products. Our research and development roadmap balances technology advances and new offerings with continuous enhancements to existing offerings. Our allocation of research and development resources is based on a cost‑benefit analysis of acquiring available technology in the marketplace versus developing our own solutions. We anticipate that we will continue to make substantial investments in research and development because we believe the infrastructure engineering software market presents compelling opportunities for the application of new technologies that advance our current solutions.

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For the year ended December 31, 2023, on a constant currency basis, research and development expenses increased primarily due to an increase in headcount‑related costs of approximately $18,730, mainly due to an increase in annual compensation costs and headcount, and to a lesser extent, realignment expenses, partially offset by a decrease in stock‑based compensation expense primarily related to the April 2023 retirement of founder and former Chief Technology Officer, Keith Bentley. The retirement of Mr. Bentley contributed to a deceleration of research and development expenses growth during 2023.

Selling and marketing. Selling and marketing expenses primarily include headcount‑related costs, as well as the expense of online marketing, product marketing and other brand‑building activities, such as advertising, trade shows, and expositions, and various sales and promotional programs. We anticipate that we will continue to make strategic investments in our global business systems and methods to enhance major account sales activities and to support our worldwide sales and marketing strategies, and the business in general.

For the year ended December 31, 2023, on a constant currency basis, selling and marketing expenses increased primarily due to an increase in headcount‑related costs of approximately $27,584, mainly due to an increase in headcount and annual compensation costs, and to a lesser extent, realignment expenses.

General and administrative. General and administrative expenses primarily include headcount‑related costs for our finance, human resources, and legal functions, as well as professional fees for legal and accounting services. General and administrative expenses also include acquisition costs, which consist of costs related to legal, accounting, valuation, insurance, and other consulting and transaction fees. Additionally, acquisition costs will drive fluctuations in general and administrative expenses depending on the timing of business combinations.

For the year ended December 31, 2023, on a constant currency basis, general and administrative expenses increased primarily due to an increase in headcount‑related costs of approximately $18,248, mainly due to an increase in headcount and annual compensation costs, and to a lesser extent, third‑party personnel costs. Partially offsetting these increases were lower non‑income related taxes of approximately $6,001 and lower acquisition expenses of approximately $5,777.

Deferred compensation plan. Deferred compensation plan reflects the expense (income) recorded related to changes in deferred compensation plan liabilities, which are marked to market at the end of each reporting period.

For the year ended December 31, 2023, deferred compensation plan expense (income) was attributable to the marked to market impact on deferred compensation plan liability balances period over period.

Amortization of purchased intangibles. Amortization of purchased intangibles includes the amortization of acquired non‑product related intangible assets, primarily customer relationships, trademarks, and non‑compete agreements recorded in connection with completed acquisitions.

For the year ended December 31, 2023, on a constant currency basis, amortization of purchased intangibles decreased primarily due to previously acquired intangible assets that continue to become fully amortized and lower acquisition activity as compared to the prior year.

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Interest Expense, Net

% Change
Year Ended December 31,20222021
202320222021to 2023to 2022
Interest expense$(41,331)$(35,056)$(11,527)17.9%NM
Interest income1,538421306NM37.6%
Interest expense, net$(39,793)$(34,635)$(11,221)14.9%NM

Percentage changes that are considered not meaningful are denoted with NM.

Interest expense, net primarily represents interest associated with the Credit Facility, the 2026 Notes, the 2027 Notes, amortization and write‑off of deferred debt issuance costs, and interest income from our investments in money market funds. The majority of our debt is protected from rising interest rates, through either very low fixed coupon interest on our convertible notes or our $200,000 interest rate swap, which expires in 2030.

For the year ended December 31, 2023, interest expense, net increased primarily due to a higher weighted average interest rate on borrowings under the Credit Facility, partially offset by lower weighted average debt outstanding.

Other (Expense) Income, Net

Year Ended December 31,
202320222021
(Loss) gain from:
Change in fair value of interest rate swap$(5,038)$27,083$9,770
Foreign exchange (1)2,497(9,901)827
Sale of aircraft2,029
Change in fair value of acquisition contingent consideration1,427(550)
Receipts (payments) related to interest rate swap8,8031,947(1,270)
Other (expense) income, net (2)(13,484)1,7131,184
Total other (expense) income, net$(7,222)$24,298$9,961

(1)Foreign exchange gain (loss) is primarily attributable to foreign currency translation derived mainly from U.S. dollar denominated cash and cash equivalents, account receivables, customer deposits, and intercompany balances held by foreign subsidiaries. Intercompany finance transactions primarily denominated in U.S. dollars resulted in unrealized foreign exchange gains (losses) of $3,163, $(7,369), and $(779) for the years ended December 31, 2023, 2022, and 2021, respectively.

(2)Other (expense) income, net includes investment impairment and other charges of $(16,988), partially offset by gains on investments of $2,360 for the year ended December 31, 2023.

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(Benefit) Provision for Income Taxes

Year Ended December 31,
202320222021
Income before income taxes$183,527$198,275$93,329
(Benefit) provision for income taxes$(143,241)$21,283$(3,448)
Effective tax rate(78.0)%10.7%(3.7)%

(Benefit) provision for income taxes includes the aggregate consolidated income tax expense for U.S. domestic and foreign income taxes.

For the year ended December 31, 2023, the effective tax rate was lower as compared to the year ended December 31, 2022 primarily due to the discrete tax benefit recognized as a result of the internal legal entity restructuring described below. The benefit of the internal legal entity restructuring was partially offset by an increase in the effective tax rate impact of the Global Intangible Low‑Taxed Income (“GILTI”) inclusion due to the mandatory capitalization of research and development expenses for U.S. tax purposes and a decrease in discrete tax benefits related to stock-based compensation, net of the impact from officer compensation limitation provisions, recognized during the current year. For the years ended December 31, 2023 and 2022, we recorded discrete tax benefits of $14,648 and $20,501, respectively, associated with windfall tax benefits from stock‑based compensation, net of the impact from officer compensation limitation provisions.

During the fourth quarter of 2023, we recognized a net discrete income tax benefit of $170,784 attributable to internal legal entity restructuring and related intra-entity transactions as part of our continuing efforts to align intellectual property ownership with our business operating model. These transactions resulted in the recognition of deferred tax benefits arising from the net increase in deferred tax assets related to intangibles and goodwill of $171,622. The deferred tax assets represent the undiscounted future anticipated cash tax impacts of basis differences, which are expected to be realized through tax amortization over the next 13 years. See Note 16 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information.

Key Business Metrics:

In addition to our results of operations discussed above, we believe the following presentation of key business metrics provides additional useful information to investors regarding our results of operations. To the extent material, we disclose below the additional purposes, if any, for which our management uses these key business metrics. Our key business metrics may vary significantly from period to period for reasons unrelated to our operating performance and may differ from similarly titled measures presented by other companies.

December 31,
202320222021
ARR$1,174,774$1,036,548$921,218
Last twelve-months recurring revenues$1,096,677$978,024$834,150
Twelve-months ended constant currency (1):
ARR growth rate12.5%15%26%
Account retention rate98%98%98%
Recurring revenues dollar-based net retention rate109%110%109%

(1)Constant currency is a non-GAAP financial measure. Refer to the “Non-GAAP Financial Measures” section for additional information, including our definition and our use of constant currency.

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Recurring Revenues

Recurring revenues are the basis for our other revenue-related key business metrics. We believe this measure is useful in evaluating our ability to consistently retain and grow our revenues within our existing accounts.

Recurring revenues are subscriptions revenues that recur monthly, quarterly, or annually with specific or automatic renewal clauses and professional services revenues in which the underlying contract is based on a fixed fee and contains automatic annual renewal provisions.

ARR

ARR is a key business metric that we believe is useful in evaluating the scale and growth of our business as well as to assist in the evaluation of underlying trends in our business. Furthermore, we believe ARR, considered in connection with our last twelve‑month recurring revenues dollar‑based net retention rate, is a leading indicator of revenue growth.

ARR is defined as the sum of the annualized value of our portfolio of contracts that produce recurring revenues as of the last day of the reporting period, and the annualized value of the last three months of recognized revenues for our contractually recurring consumption‑based software subscriptions with consumption measurement durations of less than one year, calculated using the spot foreign currency exchange rates. We believe that the last three months of recognized revenues, on an annualized basis, for our recurring software subscriptions with consumption measurement period durations of less than one year is a reasonable estimate of the annual revenues, given our consistently high retention rate and stability of usage under such subscriptions.

ARR resulting from the annualization of recurring contracts with consumption measurement durations of less than one year, as a percentage of total ARR, was 47%, 43%, and 38% as of December 31, 2023, 2022, and 2021, respectively, with our E365 subscription offering representing 41%, 35%, and 29% of total ARR as of December 31, 2023, 2022, and 2021, respectively.

In March 2022, in response to the Russia‑Ukraine war, we announced a pause of sales in Russia and Belarus, in addition to our strict compliance with applicable sanctions, regimes, and other regulatory restrictions on business activities in those countries. As a result of the conflict, we deemed our overall business recurrence in the affected countries to have been reduced by approximately 50%, and accordingly, reduced our related ARR by $5,190 as of March 31, 2022. During the second quarter of 2022, the marked shifts in the Russian business environment and economic outlook led us to conclude it was no longer viable for us to continue operations in Russia. Accordingly, we made the decision to wind down business and exit the Russian market, which resulted in a further reduction in our ARR by $6,000.

Constant currency ARR growth rate is the growth rate of ARR measured on a constant currency basis. We believe that ARR growth is an important metric indicating the scale and growth of our business.

Our ARR growth rate was favorably impacted by the ARR onboarding from our platform acquisition of PLS by 2.5% for the year ended December 31, 2022.

Last Twelve‑Months Recurring Revenues

Last twelve‑month recurring revenues is a key business metric that we believe is useful in evaluating our ability to consistently retain and grow our recurring revenues. We believe that we will continue to experience favorable growth in recurring revenues primarily due to our strong account retention and recurring revenues dollar‑based net retention rates, as well as the addition of new accounts with recurring revenues.

Last twelve‑months recurring revenues is calculated as recurring revenues recognized over the preceding twelve‑month period.

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The last twelve‑months recurring revenues for the periods ended December 31, 2023, 2022, and 2021 compared to the last twelve‑months of the comparative twelve‑month period increased by $118,653, $143,874, and $137,488, respectively. This increase was primarily due to growth in ARR, which is primarily the result of growing our recurring revenues within our existing accounts as expressed in our recurring revenues dollar‑based net retention rate, as well as additional recurring revenues resulting from new accounts and acquisitions, including the favorable impact from our platform acquisitions of PLS and Seequent. For the twelve months ended December 31, 2023, 2022, and 2021, 89%, 89%, and 86%, respectively, of our revenues were recurring revenues.

Account Retention Rate

Account retention rate is a key business metric that we believe is useful in evaluating the long‑term value of our account relationships and our ability to retain our account base. We believe that our consistent and high account retention rates illustrate our ability to retain and cultivate long‑term relationships with our accounts.

Account retention rate for any given twelve-month period is calculated using the average foreign currency exchange rates for the prior period, as follows: the prior period recurring revenues from all accounts with recurring revenues in the current and prior period, divided by total recurring revenues from all accounts during the prior period.

Recurring Revenues Dollar‑Based Net Retention Rate

Recurring revenues dollar‑based net retention rate is a key business metric that we believe is useful in evaluating our ability to consistently retain and grow our recurring revenues.

Recurring revenues dollar‑based net retention rate is calculated, using the average exchange rates for the prior period, as follows: the recurring revenues for the current period, including any growth or reductions from existing accounts, but excluding recurring revenues from any new accounts added during the current period, divided by the total recurring revenues from all accounts during the prior period. A period is defined as any trailing twelve months. Related to our platform acquisitions, recurring revenues into new accounts will be captured as existing accounts starting with the second anniversary of the acquisition when such data conforms to the calculation methodology. This may cause variability in the comparison.

Given that recurring revenues represented 89%, 89%, and 86% of our total revenues for the twelve months ended December 31, 2023, 2022, and 2021, respectively, this metric helps explain our revenue performance as primarily growth from existing accounts.

Non-GAAP Financial Measures:

In addition to our results determined in accordance with GAAP discussed above, we believe the following presentation of financial measures not in accordance with GAAP provides useful information to investors regarding our results of operations. To the extent material, we disclose below the additional purposes, if any, for which our management uses these non‑GAAP financial measures and provide reconciliations between these non‑GAAP financial measures and their most directly comparable GAAP financial measures. Non‑GAAP financial information should be considered in addition to, not as a substitute for, or in isolation from, the financial information prepared in accordance with GAAP, including operating income, or other measures of performance. Our non‑GAAP financial measures may vary significantly from period to period for reasons unrelated to our operating performance and may differ from similarly titled measures presented by other companies.

Adjusted OI w/SBC

Adjusted OI w/SBC is a non-GAAP financial measure and is used to measure the operational strength and performance of our business, as well as to assist in the evaluation of underlying trends in our business.

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Adjusted OI w/SBC is our primary performance measure, which excludes certain expenses and charges, including the non-cash amortization expense resulting from the acquisition of intangible assets, as we believe these may not be indicative of our core business operating results. We intentionally include stock-based compensation expense in this measure as we believe it better captures the economic costs of our business.

Management uses this non-GAAP financial measure to understand and compare operating results across accounting periods, for internal budgeting and forecasting purposes, to evaluate financial performance, and in our comparison of our financial results to those of other companies. It is also a significant performance measure in certain of our executive incentive compensation programs.

Adjusted OI w/SBC is defined as operating income adjusted for the following: amortization of purchased intangibles, expense (income) relating to deferred compensation plan liabilities, acquisition expenses, and realignment expenses (income), for the respective periods.

Adjusted Operating Income

Adjusted operating income is a non-GAAP financial measure that we believe is useful to investors in making comparisons to other companies, although this measure may not be directly comparable to similar measures used by other companies.

Adjusted operating income is defined as operating income adjusted for the following: amortization of purchased intangibles, expense (income) relating to deferred compensation plan liabilities, acquisition expenses, realignment expenses (income), and stock‑based compensation expense, for the respective periods.

Reconciliation of operating income to Adjusted OI w/SBC and to Adjusted operating income:

Year Ended December 31,
202320222021
Operating income$230,542$208,612$94,589
Amortization of purchased intangibles (1)51,21953,59234,001
Deferred compensation plan (2)13,580(15,782)95,046
Acquisition expenses (3)17,86625,39834,368
Realignment expenses (4)11,4702,109
Adjusted OI w/SBC324,677273,929258,004
Stock-based compensation expense (5)71,47074,56648,152
Adjusted operating income$396,147$348,495$306,156

Further explanation of certain of our adjustments in arriving at Adjusted OI w/SBC and Adjusted operating income are as follows:

(1)Amortization of purchased intangibles. Amortization of purchased intangibles varies in amount and frequency and is significantly impacted by the timing and size of our acquisitions. Management finds it useful to exclude these non‑cash charges from our operating expenses to assist in budgeting, planning, and forecasting future periods. The use of intangible assets contributed to our revenues earned during the periods presented and will also contribute to our revenues in future periods. Amortization of purchased intangible assets will recur in future periods.

(2)Deferred compensation plan. We exclude Deferred compensation plan expense (income) when we evaluate our continuing operational performance because it is not reflective of our ongoing business and results of operation. We believe it is useful for investors to understand the effects of this item on our total operating expenses. Deferred compensation plan liabilities are marked to market at the end of each reporting period, with changes in the liabilities recorded as an expense (income) to Deferred compensation plan in the consolidated statements of operations.

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(3)Acquisition expenses. We incur expenses for professional services rendered in connection with business combinations, which are included in our GAAP presentation of general and administrative expense (see Note 4 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K). Also included in our acquisition expenses are retention incentives paid to executives of the acquired companies. We exclude these acquisition expenses when we evaluate our continuing operational performance as we would not have otherwise incurred these expenses in the periods presented as part of our continuing operations. For the year ended December 31, 2022, $9,804 of our acquisition expenses related to our platform acquisition of PLS. For the year ended December 31, 2021, $16,557 and $1,644 of our acquisition expenses related to our platform acquisitions of Seequent and PLS, respectively.

(4)Realignment expenses. We exclude these charges and subsequent adjustments to our estimates when we evaluate our continuing operational performance because they are not reflective of our ongoing business and results of operations. We believe it is useful for investors to understand the effects of these items on our total operating expenses. For the year ended December 31, 2023, Realignment expenses were primarily associated with a strategic realignment program to better serve our accounts and to better align resources with the strategy of the business during the fourth quarter of 2023. In connection with these actions, we recognized $12,579 of realignment costs related to termination benefits for colleagues whose roles were impacted (see Note 21 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K). Partially offsetting these costs was income associated with the continued wind down of our Russian entities. For the year ended December 31, 2022, Realignment expenses were comprised of asset impairments and termination benefits as a result of our decision to wind down business and exit the Russian market beginning in the second quarter of 2022.

(5)Stock‑based compensation expense. We exclude non-cash stock‑based compensation expenses from certain of our non‑GAAP measures because we believe this is useful to investors in making comparisons to other companies.

Constant Currency

Constant currency and constant currency growth rates are non-GAAP financial measures that present our results of operations excluding the estimated effects of foreign currency exchange rate fluctuations. A significant amount of our operations is conducted in foreign currencies. As a result, the comparability of the financial results reported in U.S. dollars is affected by changes in foreign currency exchange rates. We use constant currency and constant currency growth rates to evaluate the underlying performance of the business, and we believe it is helpful for investors to present operating results on a comparable basis period over period to evaluate its underlying performance.

During the fourth quarter of 2023, we changed our definitions of constant currency and constant currency growth rates. In reporting period‑over‑period results, we calculate the effects of foreign currency fluctuations and constant currency information by translating current period results on a transactional basis to our reporting currency using prior period average foreign currency exchange rates in which the transactions occurred. Our prior definition of constant currency calculated the effects of foreign currency fluctuations and constant currency information by translating current period results of our subsidiaries from their functional currencies to our reporting currency by using prior period average foreign currency exchange rates in reporting period‑over‑period results.

We made this modification in order to better align with how we manage the business, to better reflect our performance during a reporting period, and to make the effects of foreign currency fluctuations and constant currency information more easily comparable on a period‑over‑period basis. Prior period amounts have been revised to conform to the current period presentation using the updated constant currency and constant currency growth rates definition. We are providing what our constant currency and constant currency growth rates results would have been pursuant to the prior definition for the applicable periods so that investors and potential investors that have analyzed these non-GAAP financial measures historically using our prior definitions can compare our historical results to our current results with respect to these non-GAAP financial measures using the prior definitions. Reconciliations of constant currency non‑GAAP financial measures and their most directly comparable GAAP financial measures under the current and prior definitions are included below.

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Reconciliation of consolidated revenues to consolidated revenues in constant currency:

Current definition:

Constant Currency % Change 2022 to 2023:

Year Ended December 31, 2023Year Ended December 31, 2022
ActualImpact of Foreign Exchange at 2022 RatesConstant CurrencyActualImpact of Foreign Exchange at 2022 RatesConstant Currency
Subscriptions$1,080,307$1,239$1,081,546$960,220$809$961,029
Perpetual licenses46,03856346,60143,3774343,420
Subscriptions and licenses1,126,3451,8021,128,1471,003,5978521,004,449
Services102,068684102,75295,48512995,614
Total revenues$1,228,413$2,486$1,230,899$1,099,082$981$1,100,063

Constant Currency % Change 2021 to 2022:

Year Ended December 31, 2022Year Ended December 31, 2021
ActualImpact of Foreign Exchange at 2021 RatesConstant CurrencyActualImpact of Foreign Exchange at 2021 RatesConstant Currency
Subscriptions$960,220$31,064$991,284$812,807$(19)$812,788
Perpetual licenses43,3772,22045,59753,080(2)53,078
Subscriptions and licenses1,003,59733,2841,036,881865,887(21)865,866
Services95,4853,54599,03099,159(11)99,148
Total revenues$1,099,082$36,829$1,135,911$965,046$(32)$965,014

Prior definition:

Year Ended December 31, 2023Year Ended December 31, 2022
ActualImpact of Foreign ExchangeConstant CurrencyActualImpact of Foreign ExchangeConstant Currency
Subscriptions$1,080,307$(8,095)$1,072,212$960,220$50,030$1,010,250
Perpetual licenses46,038(107)45,93143,3773,26946,646
Subscriptions and licenses1,126,345(8,202)1,118,1431,003,59753,2991,056,896
Services102,068538102,60695,4854,10299,587
Total revenues$1,228,413$(7,664)$1,220,749$1,099,082$57,401$1,156,483

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Reconciliation of revenues by geographic region to revenues by geographic region in constant currency:

Current definition:

Constant Currency % Change 2022 to 2023:

Year Ended December 31, 2023Year Ended December 31, 2022
ActualImpact of Foreign Exchange at 2022 RatesConstant CurrencyActualImpact of Foreign Exchange at 2022 RatesConstant Currency
Americas$650,926$242$651,168$584,794$(313)$584,481
EMEA353,550(2,841)350,709312,804151312,955
APAC223,9375,085229,022201,4841,143202,627
Total revenues$1,228,413$2,486$1,230,899$1,099,082$981$1,100,063

Constant Currency % Change 2021 to 2022:

Year Ended December 31, 2022Year Ended December 31, 2021
ActualImpact of Foreign Exchange at 2021 RatesConstant CurrencyActualImpact of Foreign Exchange at 2021 RatesConstant Currency
Americas$584,794$860$585,654$483,087$115$483,202
EMEA312,80425,696338,500300,123(348)299,775
APAC201,48410,273211,757181,836201182,037
Total revenues$1,099,082$36,829$1,135,911$965,046$(32)$965,014

Prior definition:

Year Ended December 31, 2023Year Ended December 31, 2022
ActualImpact of Foreign ExchangeConstant CurrencyActualImpact of Foreign ExchangeConstant Currency
Americas$650,926$(1,594)$649,332$584,794$5,218$590,012
EMEA353,550(6,099)347,451312,80433,524346,328
APAC223,93729223,966201,48418,659220,143
Total revenues$1,228,413$(7,664)$1,220,749$1,099,082$57,401$1,156,483

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Reconciliation of cost of revenues to cost of revenues in constant currency:

Current definition:

Constant Currency % Change 2022 to 2023:

Year Ended December 31, 2023Year Ended December 31, 2022
ActualImpact of Foreign Exchange at 2022 RatesConstant CurrencyActualImpact of Foreign Exchange at 2022 RatesConstant Currency
Cost of subscriptions and licenses$169,406$382$169,788$147,578$(45)$147,533
Cost of services96,67777297,44989,435(53)89,382
Total cost of revenues$266,083$1,154$267,237$237,013$(98)$236,915

Constant Currency % Change 2021 to 2022:

Year Ended December 31, 2022Year Ended December 31, 2021
ActualImpact of Foreign Exchange at 2021 RatesConstant CurrencyActualImpact of Foreign Exchange at 2021 RatesConstant Currency
Cost of subscriptions and licenses$147,578$4,246$151,824$124,321$(47)$124,274
Cost of services89,4354,63594,07092,218(9)92,209
Total cost of revenues$237,013$8,881$245,894$216,539$(56)$216,483

Prior definition:

Year Ended December 31, 2023Year Ended December 31, 2022
ActualImpact of Foreign ExchangeConstant CurrencyActualImpact of Foreign ExchangeConstant Currency
Cost of subscriptions and licenses$169,406$(149)$169,257$147,578$7,253$154,831
Cost of services96,67782397,50089,4354,93294,367
Total cost of revenues$266,083$674$266,757$237,013$12,185$249,198

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Reconciliation of operating expense (income) to operating expense (income) in constant currency:

Current definition:

Constant Currency % Change 2022 to 2023:

Year Ended December 31, 2023Year Ended December 31, 2022
ActualImpact of Foreign Exchange at 2022 RatesConstant CurrencyActualImpact of Foreign Exchange at 2022 RatesConstant Currency
Research and development$274,619$2,592$277,211$257,856$(36)$257,820
Selling and marketing224,336427224,763195,622(48)195,574
General and administrative180,738182180,920174,647(6)174,641
Deferred compensation plan13,58013,580(15,782)(15,782)
Amortization of purchased intangibles38,5158838,60341,1146841,182
Total operating expenses$731,788$3,289$735,077$653,457$(22)$653,435

Constant Currency % Change 2021 to 2022:

Year Ended December 31, 2022Year Ended December 31, 2021
ActualImpact of Foreign Exchange at 2021 RatesConstant CurrencyActualImpact of Foreign Exchange at 2021 RatesConstant Currency
Research and development$257,856$11,118$268,974$220,915$(15)$220,900
Selling and marketing195,6228,407204,029162,240(9)162,231
General and administrative174,6474,190178,837150,116(8)150,108
Deferred compensation plan(15,782)(15,782)95,04695,046
Amortization of purchased intangibles41,1141,75842,87225,60125,601
Total operating expenses$653,457$25,473$678,930$653,918$(32)$653,886

Prior definition:

Year Ended December 31, 2023Year Ended December 31, 2022
ActualImpact of Foreign ExchangeConstant CurrencyActualImpact of Foreign ExchangeConstant Currency
Research and development$274,619$2,491$277,110$257,856$11,791$269,647
Selling and marketing224,336615224,951195,6229,274204,896
General and administrative180,738(11)180,727174,6474,979179,626
Deferred compensation plan13,58013,580(15,782)(15,782)
Amortization of purchased intangibles38,5159538,61041,1141,68042,794
Total operating expenses$731,788$3,190$734,978$653,457$27,724$681,181

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Liquidity and Capital Resources:

Cash and Cash Equivalents

December 31,
20232022
Cash and cash equivalents held domestically$3,693$3,883
Cash and cash equivalents held by foreign subsidiaries64,71967,801
Total cash and cash equivalents$68,412$71,684

Our primary source of operating cash is from the sale of our subscriptions, perpetual licenses, and services. Our primary use of cash is payment of our operating costs, which consist mainly of headcount‑related costs. In addition to operating expenses, we also use cash to service our debt obligations, to pay quarterly dividends, to repurchase our Class B common stock and convertible debt, and for capital expenditures in support of our operations. We also use cash to fund our acquisitions of software assets and businesses, and other investment activities, including our iTwin Ventures initiative which makes seed, early, and growth stage investments in technology companies with promising and emerging opportunities for infrastructure digital twin solutions potentially relevant to our business.

During the years ended December 31, 2023 and 2022, we made cash repatriations to the U.S. of approximately $93,000 and $150,000, respectively, from earnings generated by our foreign subsidiaries. In 2023, the repatriations were used to supplement our domestic working capital requirements and to pay down our Credit Facility. In 2022, the repatriations, along with available cash and borrowings under our Credit Facility, were used to fund the acquisition of PLS in January 2022.

We believe that cash generated from operations, together with existing cash and cash equivalent balances, and external borrowings including available liquidity under the Credit Facility, will be sufficient to meet our domestic and international working capital and capital expenditure requirements. We regularly review our capital structure and consider a variety of potential financing alternatives and planning strategies to ensure that we have the proper liquidity available in the locations in which it is needed and to fund our operations and growth investments with cash that has not been permanently reinvested outside the U.S. Our future capital requirements may be materially different than those currently planned in our budgeting and forecasting activities and depend on many factors, including our strategy of regularly acquiring and integrating specialized infrastructure engineering software businesses, our rate of revenue growth, the timing and extent of spending on research and development, the expansion of our sales and marketing activities, the timing of new product introductions, market acceptance of our products, competitive factors, our discretionary payments of dividends or repurchases of our Class B common stock and convertible debt, fund of our purchase commitments, currency fluctuations, and overall economic conditions, globally. To the extent that current and anticipated future sources of liquidity are insufficient to fund our future business activities and requirements, we may be required to seek additional equity or debt financing. The sale of additional equity would result in additional dilution to our stockholders, while the incurrence of additional debt financing, including convertible debt, would result in additional debt service obligations. Such debt instruments also could introduce new or modified covenants that might restrict our operations and/or our ability to pay dividends, consummate acquisitions, or otherwise pursue our business strategies. We cannot provide assurance that we could obtain additional financing on favorable terms or at all.

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Cash Flow Activity

Year Ended December 31,
202320222021
Net cash provided by (used in):
Operating activities$416,696$274,324$288,024
Investing activities(60,504)(770,127)(1,056,603)
Financing activities(359,074)243,034982,582

Operating Activities

For the year ended December 31, 2023, compared to the prior year, net cash provided by operating activities was higher by $142,372 due to an increase in net income of $152,007 and an increase in net cash flows from the change in operating assets and liabilities of $112,542, partially offset by a net decrease in non‑cash adjustments of $122,177. Both the increase in net income and the net decrease in non‑cash adjustments were impacted by the fourth quarter of 2023 internal legal entity restructuring and related intra-entity transactions as part of our continuing efforts to align intellectual property ownership with our business operating model. The net impact of the internal legal entity restructuring was a net discrete tax benefit of $170,784. See Note 16 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information. The increase in cash flows from the change in operating assets and liabilities was primarily due to changes in accounts receivable period over period due to timing of collections from customers, higher CSS deposits, and an increase in deferred revenues period over period.

In addition, we expect cash payments of approximately $12,500 for termination benefits to colleagues in connection with our fourth quarter of 2023 strategic realignment program by mid-2024. See Note 21 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information related to realignment costs.

Investing Activities

Net cash used in investing activities was lower by $709,623 for the year ended December 31, 2023, compared to the prior year, primarily due to lower acquisition related payments, as three acquisitions were completed in 2023 compared to six acquisitions, including our platform acquisition of PLS for $695,968 in 2022.

Financing Activities

Net cash used in financing activities was $359,074 for the year ended December 31, 2023, as compared to net cash provided by financing activities of $243,034 for the year ended December 31, 2022, primarily due to the net paydown of the Credit Facility of $258,569 in 2023 as compared to an increase in net borrowings under the Credit Facility of $340,598 in 2022. Payments for shares acquired were lower during the year ended December 31, 2023 by $12,874, as compared to the prior year. The year ended December 31, 2022 payments for shares acquired includes $28,250 of share repurchases under the BSY Stock Repurchase Program (the “Repurchase Program”), whereas no repurchases were made under the Repurchase Program during 2023. Refer to the section titled “Stock Repurchases” below for further detail. Payments of dividends were higher during the year ended December 31, 2023 by $24,263 as compared to the prior year, primarily due to an increase in our quarterly dividend per share to $0.05 from $0.03.

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Long-Term Debt

December 31,
20232022
Current portion of long-term debt$10,000$5,000
Long-term debt1,518,4031,775,696
Total debt$1,528,403$1,780,696

As of December 31, 2023, we had $757,822 available under the Credit Facility. We were in compliance with all covenants in its Credit Facility, the 2026 Notes, and the 2027 Notes as of December 31, 2023. Any failure to comply with such covenants under the Credit Facility would prevent us from being able to borrow additional funds under the Credit Facility, and, as with any failure to comply with such covenants under the 2026 Notes and the 2027 Notes, could constitute a default that may cause all amounts outstanding to become due and immediately payable in full.

Our Credit Facility, 2026 Notes, and 2027 Notes are described in Note 10 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K.

Stock Repurchases

BSY Stock Repurchase Program

Our Board of Directors has authorized us to repurchase up to $200,000 of our Class B common stock and/or outstanding convertible senior notes through June 30, 2024 under the Repurchase Program. We may use available working capital and cash provided by operations to make repurchases.

For the year ended December 31, 2023, we did not repurchase shares under the Repurchase Program. For the year ended December 31, 2022, we repurchased 896,126 shares for $28,250, and $2,170 aggregate principal amount of our outstanding 2026 Notes for $1,998.

The timing, as well as the number and value of shares and/or notes repurchased under the Repurchase Program, will be determined at our discretion and will depend on a variety of factors, including our assessment of the intrinsic value of our shares, the market price of our Class B common stock and outstanding notes, general market and economic conditions, available liquidity, compliance with our debt and other agreements, and applicable legal requirements.

Withholding Taxes on Certain Equity Awards

We have the right to require that certain equity awardees receive gross or net quantities of shares of our Class B Common Stock, including in connection with share issuances under the amended and restated Bentley Systems, Incorporated Bonus Pool Plan (the “Bonus Plan”) and distributions from the DCP. In the case of a gross issuance or distribution, an awardee is required to reimburse promptly to us the cash required for his or her tax withholding amounts. Conversely, under a net issuance or distribution, shares are withheld in consideration of remitting withholding taxes on behalf of an equity awardee, thereby requiring us to remit cash for the tax withholdings. During the year ended December 31, 2023, we allowed impacted equity awardees the option to receive net quantities of shares of our Class B common stock during the first, second, and third quarters, but exercised our right to require that these awardees receive gross quantities of our Class B common stock during the fourth quarter. During the year ended December 31, 2022, we permitted impacted awardees to elect to receive net quantities of shares of our Class B common stock in the first quarter, but exercised our right to require that these awardees receive gross quantities of our Class B common stock during the second, third, and fourth quarters. We will continue to evaluate whether share awards will be required to be received by awardees on a gross basis, or if net settlement may be elected by awardees.

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Dividend Payments

The declaration and payment of dividends is within the discretion of our Board of Directors. We paid quarterly dividends of $0.05 per share of common stock during the year ended December 31, 2023 and $0.03 per share of common stock during the year ended December 31, 2022. While we intend to continue paying quarterly dividends, any future determination will be subject to the discretion of our Board of Directors and will be dependent on a number of factors, including our results of operations, capital requirements, restrictions under Delaware law, and overall financial condition, as well as any other factors our Board of Directors considers relevant. In addition, the terms of the agreement governing the Credit Facility limit the amount of dividends we can pay.

Contractual Obligations and Other Commitments:

The following table summarizes our most significant contractual obligations as of December 31, 2023:

TotalShort-TermLong-Term
Debt Obligations (1)$1,544,858$10,000$1,534,858
Purchase Obligations127,00050,00077,000
DCP Obligations90,5362,35588,181

(1)Amounts represent the face value of debt and exclude interest payments.

Our largest contractual obligations relate to our outstanding debt, which include convertible notes due in 2026 and 2027. We typically fund and expect to continue to fund debt maturities and interest payments with cash flows generated from operations, existing cash and cash equivalents, or proceeds from additional financing. If an early conversion notice is received, we have the option to pay cash, deliver shares of our Class B common stock, or a combination thereof. See Note 10 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our debt obligations.

We have non‑cancelable future cash purchase commitments for services related to the provisioning of our hosted software solutions and for other software costs. Our purchase obligations are in addition to amounts included in our consolidated balance sheets. We have funded and expect to continue to be able to fund our purchase obligations with cash flows generated from operations or existing cash and cash equivalents. See Note 18 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our purchase obligations.

Our DCP obligations represent DCP participants’ holdings in phantom investment funds, which are classified as liabilities as they will be settled in cash upon eventual distribution. We have funded and expect to continue to be able to fund our DCP obligations with cash flows generated from operations or existing cash and cash equivalents. See Note 12 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K for additional information on our DCP obligations.

Our other future contractual obligations were related to leases (see Note 8), and contingent and non‑contingent consideration from acquisitions (see Note 4). For information about those obligations, see the above referenced notes to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K.

Critical Accounting Estimates:

The preparation of our consolidated financial statements in conformity with GAAP requires us to make estimates that affect the reported amounts of assets, liabilities, revenue and expenses, and the related disclosure of contingent assets and contingent liabilities. We base our judgments on our historical experience and on various other assumptions that we believe are reasonable under the circumstances, the results of which form the basis for making estimates about the carrying value of assets and liabilities that are not readily apparent from other sources. Actual results may differ from these estimates under different assumptions or conditions.

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Revenue Recognition

Our contracts with customers may include promises to transfer licenses (perpetual or term‑based), maintenance, and services to a user. Judgment is required to determine if the promises are separate performance obligations, and if so, the allocation of the transaction price to each performance obligation. When an arrangement includes multiple performance obligations which are concurrently delivered and have the same pattern of transfer to the customer, we account for those performance obligations as a single performance obligation. For contracts with more than one performance obligation, the transaction price is allocated among the performance obligations in an amount that depicts the relative standalone selling price (“SSP”) of each obligation. Judgment is required to determine the SSP for each distinct performance obligation. In instances where SSP is not directly observable, such as when we do not sell the product or service separately, we determine the SSP using information that may include market conditions and other observable inputs. We use a range of amounts to estimate SSP when we sell each of the products and services separately and need to determine whether there is a discount that should be allocated based on the relative SSP of the various products and services.

Our SELECT agreement provides users with perpetual licenses a right to exchange software for other eligible perpetual licenses on an annual basis upon renewal. We refer to this option as portfolio balancing and concluded that the portfolio balancing feature represents a material right resulting in the deferral of the associated revenue. Judgment is required to estimate the percentage of users who may elect to portfolio balance and considers inputs such as historical user elections. This feature is available once per term and must be exercised prior to the respective renewal term. We recognize the associated revenue upon election or when the portfolio balancing right expires. This right is included in the initial and subsequent renewal terms and we reestablish the revenue deferral for the material right upon the beginning of the renewal term. Portfolio balancing exchange rights are included in Deferred revenues in the consolidated balance sheets.

Business Combinations

We allocate the fair value of the consideration transferred to the assets acquired and liabilities assumed, including trademarks, customer relationships, in‑process research and development, and acquired software and technology, based on their estimated fair values at the acquisition date. Any residual purchase price is recorded as goodwill. The purchase price allocation requires us to make significant estimates and assumptions, especially at the acquisition date, with respect to intangible assets.

Although we believe the assumptions and estimates we have made are reasonable, they are based in part on historical experience and information obtained from the management of the acquired companies and are inherently uncertain. Examples of critical estimates used in valuing certain of the intangible assets we have acquired or may acquire in the future include but are not limited to:

•future expected cash flows from total revenues and acquired developed technologies;

•the acquired company’s trade name and customer relationships as well as assumptions about the period of time the acquired trade name and customer relationships will continue to be used in our product portfolio;

•expected costs to develop the in-process research and development into commercially viable software and estimated cash flows from the projects when completed; and

•discount rates used to determine the present value of estimated future cash flows.

These estimates are inherently uncertain and unpredictable, and if different estimates were used the purchase price for the acquisition could be allocated to the acquired assets and liabilities differently from the allocation that we have made. In addition, unanticipated events and circumstances may occur, which may affect the accuracy or validity of such estimates, and, if such events occur, we may be required to record a charge against the value ascribed to an acquired asset or an increase in the amounts recorded for assumed liabilities.

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Goodwill and Other Intangible Assets

Intangible assets arise from acquisitions and principally consist of goodwill, trademarks, customer relationships, in‑process research and development, and acquired software and technology. Intangible assets, other than goodwill and in‑process research and development, are amortized on a straight‑line basis over their estimated useful lives, which range from three to ten years.

Goodwill consists of the excess of cost over the fair value of net assets acquired in business combinations. Goodwill is not amortized but instead is tested annually for impairment on October 1, or more frequently if events occur or circumstances change that would more likely than not reduce its fair value below its carrying amount. We allocate goodwill to reporting units on a relative fair value basis.

In testing for goodwill impairment, we may first qualitatively assess whether it is more likely than not (a likelihood of more than 50 percent) that a goodwill impairment exists. If it is determined that a quantitative assessment is required and the carrying amount exceeds its fair value, we will recognize goodwill impairment in the amount in which the carrying amount of the reporting unit exceeds its fair value, but not to exceed the carrying amount of goodwill within the reporting unit. There was no impairment of goodwill as a result of our annual impairment assessments conducted for the years ended December 31, 2023, 2022, or 2021.

Income Taxes

We account for income taxes under the asset and liability method, which requires the recognition of deferred tax assets and liabilities for the expected future tax consequences of events that have been included in the consolidated financial statements. Under this method, deferred tax assets and liabilities are determined based on net operating loss (“NOL”) carryforwards, credit carryforwards, and temporary differences between the financial statement and tax basis of assets and liabilities using enacted tax rates in effect for the year in which the items are expected to reverse. The effect of a change in tax rates on deferred tax assets and liabilities is recognized in income in the period of the enactment date.

We perform a quarterly assessment of the recoverability of the net deferred tax assets. We consider all available evidence, both positive and negative, in determining whether all or a portion of a deferred tax asset is more likely than not to be realized. In the event we determine that all or a portion of the deferred tax assets is not more likely than not to be realized, an adjustment to the valuation allowance would be recorded that would increase the provision for income taxes. To the extent that the realization of a deferred tax asset is based upon forecasted future earnings, our judgment regarding future profitability may change due to future market conditions and other factors. Assumptions about future taxable income require significant judgment and, while these assumptions rely heavily on estimates, such estimates are consistent with the plans we are using to manage the underlying business. Any change in future profitability may require material adjustments to these net deferred tax assets, resulting in a reduction in net income in the period when such determination is made. Additionally, future changes in tax laws and rates, including administrative or regulatory guidance, could affect recorded deferred tax assets and liabilities. Any adjustments to these estimates will generally be recorded as an income tax expense or benefit in the period the adjustment is determined.

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We are subject to income taxes in the U.S. and in numerous foreign jurisdictions. The calculation of our tax liabilities often involves dealing with uncertainties in the application of complex tax laws and regulations in a multitude of jurisdictions across our global operations. There are many transactions and calculations about which the ultimate tax outcome is uncertain. A benefit from an uncertain tax position may be recognized when it is more likely than not that the position will be sustained based upon the technical merits of the position. This may include expected resolutions upon examination, any related appeals, or through a litigation processes. As a result, our calculations involve estimates by management. Due to the complexity of some of these uncertainties, the ultimate resolution may result in a payment, potentially including interest and penalties, that is materially different from our current estimates of the unrecognized tax benefit liabilities. These differences, along with any related interest and penalties, will generally be reflected as increases or decreases to income tax expense in the period in which new information becomes available. We review the tax reserves as circumstances warrant and adjust the reserves as events occur that affect our potential liability for additional taxes. We follow the applicable guidance on derecognition, classification, interest and penalties, accounting in interim periods, disclosure, and transition with respect to uncertain tax positions. We recognize interest and penalties related to income taxes within the (Provision) benefit for income taxes line in the consolidated statements of operations. Accrued interest and penalties are included within the related tax liability line in the consolidated balance sheets.

FY 2022 10-K MD&A

SEC filing source: 0001628280-23-005568.

Extracted structurally from real Item 7 body heading to real Item 7A/8 boundary. Confidence: high. Filing date: 2023-02-28. Report date: 2022-12-31.

Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations

The following discussion should be read in conjunction with our audited consolidated financial statements and notes thereto appearing in Part II, Item 8 of this Annual Report on Form 10‑K. In addition to historical information, this discussion contains forward‑looking statements that involve risks, uncertainties, and assumptions that could cause actual results to differ materially from management’s expectations. Factors that could cause such differences are set forth in Part I, Item 1A. Risk Factors of this Annual Report on Form 10‑K. Refer to Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations in our 2021 Annual Report on Form 10‑K for management’s discussion and analysis of financial condition and results of operations for the year ended December 31, 2021 compared to the year ended December 31, 2020.

All amounts presented in this Management’s Discussion and Analysis of Financial Condition and Results of Operations, except share and per share amounts, are presented in thousands. Additionally, many of the amounts and percentages have been rounded for convenience of presentation.

Overview:

We enable infrastructure professionals and their organizations, by “going digital” through our software and cloud services offerings, to better design, build, and operate better infrastructure. We were founded in 1984 by the Bentley brothers and on September 25, 2020, we completed our IPO.

Our enduring commitment is to develop and support the most comprehensive portfolio of integrated software offerings across professional disciplines, project and asset lifecycles, infrastructure sectors, and geographies. Our software enables digital workflows across engineering disciplines, across distributed project teams, and from offices to the field. Moreover, we believe that our offerings, in particular our infrastructure digital twin solutions, empower the achievement of sustainable development goals by helping our users – infrastructure professionals – realize outcomes that are more sustainable and resilient.

We deliver our solutions via on‑premises, cloud, and hybrid environments. Our users engineer, construct, and operate projects and assets across the following infrastructure sectors:

•public works (including roads, rail, bridges, tunnels, airports, ports, and federal, state, and municipal agencies)/utilities (including networks for electricity, gas, communications, and water, wastewater, and drainage). We estimate that this sector represents 49% of the net infrastructure asset value of the global top 500 infrastructure owners based on the 2022 edition of the Bentley Infrastructure 500 Top Owners, our annual compilation of the world’s largest infrastructure owners ranked by net depreciated value of their tangible fixed assets;

•resources (including mining, oil and gas “upstream,” offshore, pipelines, environmental management, and renewable energy). We estimate that this sector represents 21% of the global top 500 infrastructure owners’ net infrastructure asset value;

•industrial (including discrete and process manufacturing, oil and gas “downstream,” and power generation). We estimate that this sector represents 18% of the global top 500 infrastructure owners’ net infrastructure asset value; and

•commercial/facilities (including office buildings, retail facilities, hospitals, and campuses). We estimate that this sector represents 12% of the global top 500 infrastructure owners’ net infrastructure asset value.

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We offer solutions for enterprises and professionals across the infrastructure lifecycle. Our engineering applications and geoprofessional applications support the breadth of engineering and geoprofessional disciplines and are primarily desktop applications for professional practitioners. Our project delivery and asset performance Enterprise Systems are provided via cloud and hybrid environments, developed respectively to extend enterprise collaboration during project delivery, and to manage and leverage engineering information during operations and maintenance. Our Industry Solutions solve domain‑specific problems for owners of infrastructure assets, and the project delivery ecosystems that support these owners. Our cloud-native iTwin Platform solutions enable digital twin workflows, which can span project and asset lifecycles.

We continue to make substantial investments in research and development because we believe the infrastructure engineering software market presents compelling opportunities for the application of new technologies that advance our current solutions. Our research and development roadmap balances technology advances and new offerings with continuous enhancements to existing offerings. Our allocation of research and development resources is guided by management‑established priorities, input from product managers, and user and sales force feedback.

We bring our offerings to market primarily through direct sales channels that generated approximately 92% of our 2022 total revenues.

Since its founding, Bentley Systems has remained focused on our mission to provide software in support of the professional needs of those responsible for creating and managing the world’s infrastructure. We have methodically grown through periods of global expansion, periods of expansion in our portfolio of solutions, and periods of rapid technological change. The following provides key corporate milestones over our 38‑year history:

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Our sources of revenue growth, excluding the impact from acquisitions, come from additional subscriptions revenues from existing accounts using the same products and represent the majority of our revenue growth, additional subscriptions revenues from existing accounts using new products, and subscriptions revenues from new accounts. For the year ended December 31, 2022, subscriptions represented 87% of our total revenues, and together with certain services revenues that are recurring in nature and represented 2% of our total revenues, brought the proportion of our recurring revenues to 89% of our total revenues. The remaining 11% of our revenues were generated from the sale of perpetual licenses and the delivery of non‑recurring services. We have a highly‑diversified account base, with our largest account representing no more than 2% of our total revenues in 2022. Our 2022 total revenues were also diversified by account type, size, and geography. Additionally, we believe that we have a loyal account base, with over 70% of our 2022 total revenues from organizations that have been our accounts for over ten years.

Our Commercial Offerings:

Our solutions are made available to our accounts in a broad range of commercial offerings designed to accommodate the diverse preferences of our accounts, which range from owned versus subscribed, short‑term subscriptions versus annual subscriptions, and fee‑certain arrangements versus variable or consumption‑based arrangements with consumption measurement durations of less than one year. We contract our commercial offerings under a single form of standard contract, which includes liability and other risk protections in our favor, and appropriate standard addendums to the primary contract, which specifically address the commercial offerings provided. Our standard commercial offerings are summarized in the table below, with further descriptions following the table:

Enterprise Subscriptions. Our enterprise subscription offerings provide our enterprise accounts with complete and unlimited global access to our comprehensive portfolio of solutions.

•Enterprise 365 (“E365”) Subscriptions. Under our E365 subscription, accounts are charged primarily based upon daily usage. E365 subscriptions can contain quarterly usage floors or collars. The daily usage fee includes a term license component, SELECT maintenance and support, hosting, and Success Blueprints, which are designed to achieve business outcomes through more efficient and effective use of our software.

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•Enterprise License Subscriptions (“ELS”). Under our ELS offering, accounts are charged based upon a fixed annual fee. Subsequent annual renewals are based on the account’s usage of software in the preceding year, effectively resulting in a fee‑certain annual consumption‑based arrangement. We are completing efforts to transition ELS subscribers to E365 subscriptions, primarily to simplify pricing, more closely align consumption to monetization, and to establish Success Blueprints as recurring to ensure better business outcomes for our users. In transitioning subscribers to E365, we recognize a greater proportion of our revenues on a quarterly basis rather than substantially upfront.

SELECT Subscriptions. Our SELECT subscription is a prepaid annual recurring subscription that accompanies a new or previously purchased perpetual license. We believe that the SELECT benefits summarized below support our favorable rates of account retention and growth:

•Software upgrades;

•Comprehensive technical support;

•License pooling providing accounts with efficiency advantages;

•Portfolio balancing providing accounts the opportunity to exchange unused or under used licenses with other of our license offerings;

•Learning benefits, Azure‑based cloud collaboration services, and mobility advantages; and

•Access to our entire application portfolio with usage of licenses not previously purchased monetized quarterly in arrears based on consumption. See the section titled “—Term License Subscriptions” below.

Term License Subscriptions

Annual Term Licenses (“ATL”) Subscription. Annual term licenses are generally prepaid annually for named user access to specific products and include our Virtuoso subscriptions sold via our Virtuosity eStore for practitioner licenses. Virtuoso subscriptions are bundles with customizable training and expert consultation administered through “keys” or credits. ATL are also used to monetize site or enterprise wide access for certain of our AssetWise solutions within given usage bands.

Quarterly Term License (“QTL”) Subscription. Through quarterly term licenses, accounts pay quarterly in arrears for licenses they have used representing usage beyond their contracted quantities. Much like our enterprise subscription programs, a QTL allows smaller- and medium‑sized accounts to match usage to ongoing project requirements.

Monthly Term License (“MTL”) Subscription. Monthly term licenses are identical to QTL subscriptions, except for the term of the license, and the manner in which they are monetized. MTL subscriptions require a Cloud Services Subscription, which is discussed below.

Visas. Visas are quarterly or annual term licenses enabling users to access specific project or enterprise information and entitles our users to certain functionality of our ProjectWise and AssetWise systems. Generally, a Visa provides desktop, web, and mobile application access to project information and certain functions, plus added functionality depending upon the product to which the Visa is aligned.

While certain legacy arrangements are supported, our standard offering requires Visas to be fulfilled and contracted via a CSS, which is discussed below.

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Cloud Services Subscription (“CSS”). CSS is designed to streamline the procurement, administration, and payment process for us and our accounts. A CSS requires an upfront annual estimation of MTL, Visa consumption, and any Success Services expected for the upcoming year. A deposit for the annual estimated consumption is submitted in advance. Actual consumption is monitored and invoiced against the deposit on a calendar quarter basis. Accounts are charged only for what gets used and deposited amounts never expire.

Perpetual Licenses

We historically have sold perpetual licenses and continue to offer them to our accounts as an available option for most of our applications. Perpetual licenses are available for accounts that prefer to own their software licenses and may be sold with or without attaching a SELECT subscription. Historically, attachment and retention of the SELECT subscription has been high given the benefits of the SELECT subscription.

Services

We provide professional services, including training, implementation, configuration, customization, and strategic consulting services. We perform projects on both a time and materials and a fixed fee basis. Certain of our fixed‑fee arrangements, including our Success Services offerings, are structured as subscription‑like, packaged offerings that are annually recurring in nature. Success Services are standard service offerings that provide a level of dedicated professional services above the standard technical support offered to all accounts as part of their SELECT or enterprise agreement.

Key Business Metrics:

We regularly review the following key metrics to evaluate our business, measure our performance, identify trends in our business, prepare financial projections, and make strategic decisions.

December 31,
202220212020
Annualized recurring revenues (“ARR”)$1,036,548$921,218$752,697
Last twelve-months recurring revenues$978,024$834,150$696,662
Twelve-months ended constant currency:
ARR growth rate15%26%8%
Account retention rate98%98%98%
Recurring revenues dollar-based net retention rate110%109%107%

ARR. Our ARR is defined as the sum of the annualized value of our portfolio of contracts that produce recurring revenues as of the last day of the reporting period, and the annualized value of the last three months of recognized revenues for our contractually recurring consumption‑based software subscriptions with consumption measurement durations of less than one year, calculated using the spot foreign exchange rates. We believe that the last three months of recognized revenues, on an annualized basis, for our recurring software subscriptions with consumption measurement period durations of less than one year is a reasonable estimate of the annual revenues, given our consistently high retention rate and stability of usage under such subscriptions. ARR resulting from the annualization of recurring contracts with consumption measurement durations of less than one year, as a percentage of total ARR, was 43%, 38%, and 36% as of December 31, 2022, 2021, and 2020, respectively. Within our consumption‑measured ARR, the continuous uptake of our E365 subscription offering has increased daily consumption‑measured ARR, representing 35% of total ARR as of December 31, 2022. We believe that ARR is an important metric indicating the scale and growth of our business. Furthermore, we believe ARR, considered in connection with our recurring revenues dollar‑based net retention rate, is a leading indicator of revenue growth.

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In March 2022, in response to the Russia‑Ukraine war, we announced a pause of sales in Russia and Belarus, in addition to our strict compliance with applicable sanctions, regimes, and other regulatory restrictions on business activities in those countries. As a result of the conflict, we deemed our overall business recurrence in the affected countries to have been reduced by approximately 50%, and accordingly, reduced our related ARR by $5,190 as of March 31, 2022. During the second quarter of 2022, the marked shifts in the Russian business environment and economic outlook led us to conclude it was no longer viable for us to continue operations in Russia. Accordingly, we made the decision to wind down business and exit the Russian market, which resulted in a further reduction in our ARR by $6,000.

Last twelve‑months recurring revenues. Last twelve‑months recurring revenues is calculated as recurring revenues recognized over the preceding twelve‑month period. We define recurring revenues as subscriptions revenues that recur monthly, quarterly, or annually with specific or automatic renewal clauses and services revenues in which the underlying contract is based on a fixed fee and contains automatic annual renewal provisions.

We believe that last twelve‑months recurring revenues is an important indicator of our performance during the immediately preceding twelve‑month time period. We believe that we will continue to experience favorable growth in recurring revenues primarily due to our strong account retention and recurring revenues dollar‑based net retention rates, as well as the addition of new accounts with recurring revenues. The last twelve‑months recurring revenues for the periods ended December 31, 2022, 2021, and 2020 compared to the last twelve‑months of the preceding twelve‑month period increased by $143,874, $137,488, and $65,565, respectively. This increase was primarily due to growth in ARR, which is primarily the result of growing our recurring revenues within our existing accounts as expressed in our recurring revenues dollar‑based net retention rate, as well as additional recurring revenues resulting from new accounts and acquisitions, including the favorable impact from our platform acquisitions of Power Line Systems and Seequent. For the twelve months ended December 31, 2022, 2021, and 2020, 89%, 86%, and 87%, respectively, of our revenues were recurring revenues.

Constant currency metrics. In reporting period‑over‑period results, we calculate the effects of foreign currency fluctuations and constant currency information by translating current period results using prior period average foreign currency exchange rates. Our definition of constant currency may differ from other companies reporting similarly named measures, and these constant currency performance measures should be viewed in addition to, and not as a substitute for, our operating performance measures calculated in accordance with U.S. GAAP.

ARR growth rate. Our ARR growth rate is the growth rate of our ARR, measured on a constant currency basis. Our ARR growth rate was favorably impacted by the ARR onboarding from our platform acquisition of Power Line Systems by 2.5% for the year ended December 31, 2022 and by 13% for the year ended December 31, 2021 due to the ARR onboarding from our platform acquisition of Seequent. We believe that ARR growth is an important metric indicating the scale and growth of our business.

Account retention rate. Our account retention rate for any given twelve-month period is calculated using the average currency exchange rates for the prior period, as follows: the prior period recurring revenues from all accounts with recurring revenues in the current and prior period, divided by total recurring revenues from all accounts during the prior period. Our account retention rate is an important indicator that provides insight into the long‑term value of our account relationships and our ability to retain our account base. We believe that our consistent and high account retention rates illustrate our ability to retain and cultivate long‑term relationships with our accounts.

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Recurring revenues dollar‑based net retention rate. Our recurring revenues dollar‑based net retention rate is calculated using the average exchange rates for the prior period, as follows: the recurring revenues for the current period, including any growth or reductions from existing accounts, but excluding recurring revenues from any new accounts added during the current period, divided by the total recurring revenues from all accounts during the prior period. A period is defined as any trailing twelve months. Related to our platform acquisitions, recurring revenues into new accounts will be captured as existing accounts starting with the second anniversary of the acquisition when such data conforms to the calculation methodology. This may cause variability in the comparison. We believe our recurring revenues dollar‑based net retention rate is a key indicator of our success in growing our revenues within our existing accounts. Given that recurring revenues represented 89% of our total revenues for the twelve months ended December 31, 2022, this metric helps explain our revenue performance, excluding the impact from acquisitions, as primarily growth into existing accounts. We believe that our consistent and high recurring revenues dollar‑based net retention rate illustrates our ability to consistently retain accounts and grow them.

Our calculation of these metrics may not be comparable to other companies with similarly‑titled metrics.

Non-GAAP Financial Measures:

In addition to our results determined in accordance with U.S. GAAP, we also use the below non‑GAAP financial information to evaluate our ongoing operations and for internal planning and forecasting purposes.

Year Ended December 31,
202220212020
Adjusted EBITDA$366,440$324,948$266,376
Adjusted Net Income274,518267,892193,334

Adjusted EBITDA. We define Adjusted EBITDA as net income adjusted for interest expense, net, provision (benefit) for income taxes, depreciation and amortization, stock‑based compensation, expense (income) relating to deferred compensation plan liabilities, acquisition expenses, realignment expenses, expenses associated with IPO, other non‑operating (income) expense, net, and (income) loss from investments accounted for using the equity method, net of tax.

Adjusted Net Income. We define Adjusted Net Income as net income adjusted for the following: amortization of purchased intangibles, stock‑based compensation, expense (income) relating to deferred compensation plan liabilities, acquisition expenses, realignment expenses, expenses associated with IPO, other non‑operating (income) expense, net, the tax effect of the above adjustments to net income, and (income) loss from investments accounted for using the equity method, net of tax. The income tax effect of non‑GAAP adjustments was determined using the applicable rates in the taxing jurisdictions in which income or expense occurred, and represent both current and deferred income tax expense or benefit based on the nature of the non‑GAAP adjustments, including the tax effects of non‑cash stock‑based compensation expense.

Adjusted EBITDA and Adjusted Net Income are not presentations made in accordance with U.S. GAAP, and our use of the terms Adjusted EBITDA and Adjusted Net Income may vary from the use of similarly titled measures by others in our industry due to the potential inconsistencies in the method of calculation and differences due to items subject to interpretation. We believe the presentation of Adjusted EBITDA and Adjusted Net Income provides useful information to management and investors regarding financial and business trends related to our results of operations and that when non‑GAAP financial information is viewed with U.S. GAAP financial information, investors are provided with a more meaningful understanding of our ongoing operating performance. We also use Adjusted EBITDA and Adjusted Net Income to compare our results to those of our competitors and to consistently measure our performance from period to period.

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Adjusted EBITDA and Adjusted Net Income should not be considered as alternatives to net income, operating income, or any other performance measures derived in accordance with U.S. GAAP as measures of operating performance. Adjusted EBITDA and Adjusted Net Income have important limitations as analytical tools and should not be considered in isolation or as a substitute for analysis of our results as reported under U.S. GAAP.

Reconciliation of net income to Adjusted EBITDA:

Year Ended December 31,
202220212020
Net income$174,780$93,192$126,521
Interest expense, net34,63511,2216,780
Provision (benefit) for income taxes21,283(3,448)38,625
Depreciation and amortization71,53752,79336,117
Stock-based compensation (2)74,56648,15232,114
Deferred compensation plan (3)(15,782)95,046177
Acquisition expenses (4)25,39834,36811,666
Realignment expenses (5)2,10910,022
Expenses associated with IPO (6)26,130
Other income, net (7)(24,298)(9,961)(24,250)
Loss from investments accounted for using the equity method, net of tax2,2123,5852,474
Adjusted EBITDA$366,440$324,948$266,376

Reconciliation of net income to Adjusted Net Income:

Year Ended December 31,
202220212020
Net income$174,780$93,192$126,521
Non-GAAP adjustments, prior to income taxes:
Amortization of purchased intangibles (1)53,59234,00120,721
Stock-based compensation (2)74,56648,15232,114
Deferred compensation plan (3)(15,782)95,046177
Acquisition expenses (4)25,39834,36811,666
Realignment expenses (5)2,10910,022
Expenses associated with IPO (6)26,130
Other income, net (7)(24,298)(9,961)(24,250)
Total non-GAAP adjustments, prior to income taxes115,585201,60676,580
Income tax effect of non-GAAP adjustments(18,059)(30,491)(12,241)
Loss from investments accounted for using the equity method, net of tax2,2123,5852,474
Adjusted Net Income$274,518$267,892$193,334

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Further explanation of certain of our adjustments in arriving at Adjusted EBITDA and Adjusted Net Income are as follows:

(1)Amortization of purchased intangibles. Amortization of purchased intangibles varies in amount and frequency and is significantly impacted by the timing and size of our acquisitions. Management finds it useful to exclude these non‑cash charges from our operating expenses to assist in budgeting, planning, and forecasting future periods. The use of intangible assets contributed to our revenues earned during the periods presented and will also contribute to our revenues in future periods. Amortization of purchased intangible assets will recur in future periods.

(2)Stock‑based compensation. We exclude certain stock‑based compensation expenses from our non‑GAAP measures primarily because they are non‑cash expenses and management finds it useful to exclude certain non‑cash charges to assess the appropriate level of various operating expenses to assist in budgeting, planning, and forecasting future periods. Moreover, because of the variety of award types and subjective assumptions made in recognizing stock‑based compensation expense, we believe excluding stock‑based compensation expenses allows investors to make meaningful comparisons between our recurring core business results of operations and those of other companies.

(3)Deferred compensation plan. In August 2021, our board of directors approved an amendment to the amended and restated Bentley Systems, Incorporated Nonqualified Deferred Compensation Plan (the “DCP”), which offered to certain active executives in the DCP a one‑time, short‑term election to reallocate a limited portion of their DCP holdings from phantom shares of the Company’s Class B Common Stock into other phantom investment funds. The offer to reallocate was subject to a proration mechanism which adjusted the aggregate elections to a maximum of 1,500,000 phantom shares of the Company’s Class B Common Stock. This one‑time reallocation opportunity was offered only to certain active executives (but not to Directors or Bentley family members) in order to encourage retention, as otherwise these executives could only have materially diversified their investments in Company equity (primarily held in the DCP) by voluntarily terminating employment to trigger DCP distributions. These executives in aggregate accordingly diversified 24% of their phantom shares of the Company’s Class B Common Stock. While DCP participants’ investments in phantom shares remain equity classified, as they will be settled in shares of Class B Common Stock upon eventual distribution, the amendment and elections resulted in a change to liability classification for the reallocated phantom investments, as they will be settled in cash upon eventual distribution. As a result, during the year ended December 31, 2021, we recognized a one‑time compensation charge of $90,721 to Deferred compensation plan expenses in the consolidated statement of operations to record the reallocated deferred compensation plan liabilities at their fair value. Deferred compensation plan liabilities are marked to market at the end of each reporting period, with changes in the liabilities recorded as an expense (income) to Deferred compensation plan in the consolidated statements of operations. We exclude Deferred compensation plan expense (income) when we evaluate our continuing operational performance because it is not reflective of our ongoing business and results of operation. We believe it is useful for investors to understand the effects of this item on our total operating expenses.

(4)Acquisition expenses. We incur expenses for professional services rendered in connection with business combinations, which are included in our U.S. GAAP presentation of general and administrative expense (See Note 4 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K). Also included in our acquisition expenses are retention incentives paid to executives of the acquired companies. For the year ended December 31, 2022, $9,804 of our acquisition expenses related to our platform acquisition of Power Line Systems. For the year ended December 31, 2021, $16,557 and $1,644 of our acquisition expenses related to our platform acquisitions of Seequent and Power Line Systems, respectively. We exclude these acquisition expenses when we evaluate our continuing operational performance as we would not have otherwise incurred these expenses in the periods presented as part of our continuing operations.

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(5)Realignment expenses. During 2022, the marked shifts in the Russian business environment and economic outlook led us to conclude it was no longer viable for us to continue operations in Russia. Accordingly, we made the decision to wind down business and exit the Russian market. As a result, we incurred exit costs, which were comprised of termination benefits for colleagues whose positions were eliminated and asset impairments. During 2020, these expenses were associated with realigning our business strategies to better serve our accounts and to better align resources with the evolving needs of the business. In connection with these actions, we recognized costs related to termination benefits for colleagues whose positions were eliminated. We exclude these charges and subsequent adjustments to our estimates when we evaluate our continuing operational performance because they are not reflective of our ongoing business and results of operations. We believe it is useful for investors to understand the effects of these items on our total operating expenses. In the ordinary course of operating our business, we incur severance expenses that are not included in this adjustment.

(6)Expenses associated with IPO. These expenses include certain non-recurring costs relating to our IPO, consisting of the payment of underwriting discounts and commissions applicable to the sale of shares by the selling stockholders, professional fees, and other expenses. We exclude these charges because they are not reflective of our ongoing business and results of operation. We believe it is useful for investors to understand the effects of these items on our total operating expenses.

(7)Other income, net. The table below contains the details of Other income, net. We exclude these items because they are not reflective of our ongoing business and results of operations. We believe it is useful for investors to understand the effects of these items on our results of operations.

Year Ended December 31,
202220212020
(Gain) loss from:
Change in fair value of interest rate swap$(27,083)$(9,770)$(347)
Foreign exchange (a)9,901(827)(22,919)
Sale of aircraft(2,029)
Change in fair value of acquisition contingent consideration(1,427)550(1,340)
Payments related to interest rate swap(1,947)1,270696
Other income, net(1,713)(1,184)(340)
Total other income, net$(24,298)$(9,961)$(24,250)

(a)Foreign exchange loss (gain) is primarily attributable to foreign currency translation derived mainly from U.S. Dollar denominated cash and cash equivalents, account receivables, customer deposits, and intercompany balances held by foreign subsidiaries. Intercompany finance transactions primarily denominated in U.S. Dollars resulted in unrealized foreign exchange losses (gains) of $7,369, $779, and $(22,310) for the years ended December 31, 2022, 2021, and 2020, respectively.

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Key Factors Impacting Comparability and Performance:

In addition to our performance previously discussed in “—Key Business Metrics” and “—Non-GAAP Financial Measures,” and as discussed further below in “—Results of Operations” and “—Liquidity and Capital Resources,” our consolidated financial statements were impacted by the following:

Acquisitions. Since our founding, we have purposefully pursued a strategy of regularly acquiring and integrating specialized infrastructure engineering software businesses. As a public company, we have been able to make platform acquisitions which appreciably increase our scale and/or the scope of our platform capabilities. Our relatively numerous and frequent programmatic acquisitions, which most often “fill white space” within our ecosystem and add their particular value principally by virtue of our existing platform comprehensiveness, and accordingly we consider this programmatic aspect of our growth as characteristically within our mainstream business performance (unlike platform acquisitions).

We completed 6, 13, and 6 acquisitions for the years ended December 31, 2022, 2021, and 2020, respectively. Our year ended December 31, 2022 consolidated financial statements were meaningfully impacted by our platform acquisition of Power Line Systems, which was completed on January 31, 2022 for $695,968 in cash, net of cash acquired. Our year ended December 31, 2022 and 2021 consolidated financial statements were meaningfully impacted by our platform acquisition of Seequent, which was completed on June 17, 2021 for $883,336 in cash, net of cash acquired, plus 3,141,342 shares of our Class B Common Stock. For the year ended December 31, 2022, $9,804 of our acquisition expenses related to the acquisition of Power Line Systems. For the year ended December 31, 2021, $16,557 and $1,644 of our acquisition expenses related to the acquisitions of Seequent and Power Line Systems, respectively.

DCP Amendment. In August 2021, our board of directors approved an amendment to the DCP, which offered to certain active executives in the DCP a one‑time, short‑term election to reallocate a limited portion of their DCP holdings from phantom shares of our Class B Common Stock into other phantom investment funds. The offer to reallocate was subject to a proration mechanism which adjusted the aggregate elections to a maximum of 1,500,000 phantom shares of the Company’s Class B Common Stock. This one‑time reallocation opportunity was offered only to certain active executives (but not to Directors or Bentley family members) in order to encourage retention, as otherwise these executives could only have materially diversified their investments in Company equity (primarily held in the DCP) by voluntarily terminating employment to trigger DCP distributions. These executives in aggregate accordingly diversified 24% of their phantom shares of the Company’s Class B Common Stock. While DCP participants’ investments in phantom shares remain equity classified, as they will be settled in shares of Class B Common Stock upon eventual distribution, the amendment and elections resulted in a change to liability classification for the reallocated phantom investments, as they will be settled in cash upon eventual distribution. As a result, during the year ended December 31, 2021, we recognized a one‑time compensation charge of $90,721 to Deferred compensation plan expenses in the consolidated statement of operations to record the reallocated deferred compensation plan liabilities at their fair value. Subsequent to the one‑time reallocation, these diversified deferred compensation plan liabilities are marked to market at the end of each reporting period, with changes in the liabilities recorded as an expense (income) to Deferred compensation plan in the consolidated statements of operations.

BSY Stock Repurchase Program. On May 11, 2022, we announced that our board of directors approved the BSY Stock Repurchase Program (the “Repurchase Program”) authorizing us to repurchase up to $200,000 of our Class B Common Stock through June 30, 2024. On December 14, 2022, our board of directors amended the Repurchase Program to allow us also to repurchase its outstanding convertible senior notes. This additional authorization did not increase the overall dollar limit of the Repurchase Program. For the year ended December 31, 2022, we repurchased 896,126 shares for $28,250, and $2,170 aggregate principal amount of our outstanding 2026 Notes for $1,998.

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Impact of foreign currency. A portion of our total revenues and operating expenses were derived from outside the U.S. and, as such, were denominated in various foreign currencies, including most significantly: Euros, British Pounds, Canadian Dollars, Australian Dollars, Chinese Yuan Renminbi, and New Zealand Dollars. Our financial results are therefore affected by changes in foreign currency rates. For the years ended December 31, 2022, 2021, and 2020, 36%, 47%, and 43%, respectively, of our total revenues were denominated in various foreign currencies. Correspondingly, for the years ended December 31, 2022, 2021, and 2020, 46%, 42%, and 46%, respectively, of our total operating expenses were denominated in various foreign currencies. Other than the natural hedge attributable to matching revenues and expenses in the same currencies, we do not currently hedge foreign currency exposure. Accordingly, our results of operations have been, and in the future will be, affected by changes in foreign exchange rates.

We identify the effects of foreign currency on our operations and present constant currency growth rates and fluctuations because we believe exchange rates are an important factor in understanding period‑over‑period comparisons and enhance the understanding of our results and evaluation of our performance. In reporting period-over-period results, we calculate the effects of foreign currency fluctuations and constant currency information by translating current period results using prior period average foreign currency exchange rates. Our definition of constant currency may differ from other companies reporting similarly named measures, and these constant currency performance measures should be viewed in addition to, and not as a substitute for, our operating performance measures calculated in accordance with U.S. GAAP.

Components of Results of Operations:

We manage our business globally within one operating segment, the development and marketing of computer software and related services, which is consistent with how our chief operating decision maker reviews and manages our business.

Revenues

We generate revenues from subscriptions, perpetual licenses, and services.

Subscriptions

Enterprise subscriptions. We provide enterprise subscription offerings, which provide our enterprise accounts with complete and unlimited global access to our comprehensive portfolio of solutions. Our E365 subscriptions are charged to accounts primarily based upon daily usage. The daily usage fee includes a term license component, SELECT maintenance and support, hosting, and Success Blueprints, which are designed to achieve business outcomes through more efficient and effective use of our software. E365 subscriptions can contain quarterly usage floors or collars. Alternatively, ELS provides access for a prepaid fee, which is based on the account’s usage of software in the preceding year, to effectively create a fee‑certain consumption‑based arrangement. ELS contain a term license component, SELECT maintenance and support, and performance consulting days. The E365 and ELS offerings both contain a distinct term license component. E365 revenues are recognized based upon usage incurred by the account. ELS revenues are recognized as the distinct performance obligations are satisfied.

SELECT subscriptions. We provide prepaid annual recurring subscriptions that accompanies a new or previously purchased perpetual license. SELECT provides accounts with benefits, including upgrades, comprehensive technical support, pooled licensing benefits, annual portfolio balancing exchange rights, learning benefits, certain Azure‑based cloud collaboration services, mobility advantages, and access to other available benefits. SELECT subscriptions revenues are recognized as distinct performance obligations are satisfied.

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Term license subscriptions. We provide annual, quarterly, and monthly term licenses for our software products. ATL subscriptions are generally prepaid annually for named user access to specific products and include our Virtuoso subscriptions sold via our Virtuosity eStore for practitioner licenses. Virtuoso subscriptions are bundles with customizable training and expert consultation administered through “keys” or credits. QTL subscriptions allow accounts to pay quarterly in arrears for license usage that is beyond their contracted quantities. MTL subscriptions are identical to QTL subscriptions, except for the term of the license, and the manner in which they are monetized. MTL subscriptions require a CSS, which is described below.

Visas are quarterly or annual term licenses enabling users to access specific project or enterprise information and entitles users to certain functionality of our ProjectWise and AssetWise systems. Our standard offerings are usage based with monetization through our CSS program as described below. Annual, quarterly, and monthly term licenses revenues are recognized as the distinct performance obligations for each are satisfied. Billings in advance are recorded as Deferred revenues in the consolidated balance sheets. QTL, MTL, and Visas subscriptions are recognized based upon usage incurred by the account.

CSS is a program designed to streamline the procurement, administration, and payment process. The program requires an estimation of annual usage for CSS eligible offerings and a deposit of funds in advance Actual consumption is monitored and invoiced against the deposit on a calendar quarter basis. CSS balances not utilized for eligible products or services may roll over to future periods or are refundable. Paid and unconsumed CSS balances are recorded in Accruals and other current liabilities in the consolidated balance sheets. Software and services consumed under CSS are recognized pursuant to the applicable revenue recognition guidance for the respective software or service and classified as subscriptions or services based on their respective nature.

Perpetual licenses

Perpetual licenses may be sold with or without attaching a SELECT subscription. Historically, attachment and retention of the SELECT subscription has been high given the benefits of the SELECT subscription discussed above. Perpetual licenses revenues are recognized upon delivery of the license to the user.

Services

We provide professional services, including training, implementation, configuration, customization, and strategic consulting services. We perform projects on both a time and materials and a fixed fee basis. Certain of our fixed‑fee arrangements, including our Success Services offerings, are structured as subscription‑like, packaged offerings that are annually recurring in nature. Success Services are standard service offerings that provide a level of dedicated professional services above the standard technical support offered to all accounts as part of their SELECT or enterprise agreement. Revenues are recognized as services are performed.

Headcount-related costs

For the years ended December 31, 2022, 2021, and 2020, approximately 80% of our aggregate cost of revenues, research and development, selling and marketing, and general and administrative expenses were represented by what we refer to herein as “headcount-related” costs. These costs primarily include salaries, incentives, benefits, employment taxes, travel, and realignment of our colleagues, and third‑party personnel and related overhead. Our headcount‑related costs are variable in nature. We actively manage these costs to align to our trending run rate of revenue performance, with the objective of enhancing visibility and predictability of resulting operating profit margins.

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Cost of subscriptions, licenses, and services

Cost of subscriptions and licenses. Cost of subscriptions and licenses includes salaries and other related costs, including the depreciation of property and equipment and the amortization of capitalized software costs associated with servicing software subscriptions, the amortization of intangible assets associated with acquired software and technology, channel partner compensation for providing sales coverage to subscribers, as well as cloud‑related costs incurred for servicing our accounts using cloud provisioned solutions and our license administration platform.

Cost of services. Cost of services includes salaries for internal and third‑party personnel and related overhead costs, including depreciation of property and equipment and amortization of capitalized software costs, for providing training, implementation, configuration, and customization services to accounts.

Operating expense (income)

Research and development. Research and development expenses, which are generally expensed as incurred, primarily consist of personnel and related costs of our research and development staff, including salaries, incentives, and benefits, and costs of certain third‑party contractors, as well as allocated overhead costs. We expense software development costs, including costs to develop software products or the software component of products to be sold, leased, or marketed to external accounts, before technological feasibility is reached. In general, technological feasibility is reached shortly before the release of such products.

Under our Accelerated Commercial Development Program (“ACDP”) (our structured approach to an in‑house business incubator function), we capitalize certain development costs related to certain projects once technological feasibility is established. Technological feasibility is established when a detailed program design has been completed and documented; we have established that the necessary skills, hardware, and software technology are available to produce the product; and there are no unresolved high‑risk development issues. Once the software is ready for its intended use, amortization is recorded over the software’s estimated useful life (generally three years). Total costs capitalized under the ACDP were $7,060, $6,608, and $7,809 for the years ended December 31, 2022, 2021, and 2020, respectively. Additionally, total ACDP related amortization recorded in Costs of subscriptions and licenses was $6,626, $7,020, and $4,699 for the years ended December 31, 2022, 2021, and 2020, respectively.

Selling and marketing. Selling and marketing expenses include salaries, benefits, bonuses, and stock‑based compensation expense for our selling and marketing colleagues, the expense of travel, entertainment, and training for such personnel, online marketing, product marketing and other brand‑building activities, such as advertising, trade shows, and expositions, various sales and promotional programs, and costs of computer equipment and facilities used in selling and marketing activities. We anticipate that we will continue to make strategic investments in our global business systems and methods to enhance major account sales activities and to support our worldwide sales and marketing strategies, and the business in general. We capitalize certain incremental costs of obtaining a contract and recognize these expenses over the period of benefit associated with these costs, resulting in a deferral of certain contract costs each period. The contract costs are amortized based on the economic life of the goods and services to which the contract costs relate. We apply a practical expedient to expense costs as incurred for costs to obtain a contract with a customer when the amortization period would have been one year or less. These costs include our internal sales force compensation program and certain channel partner sales incentive programs for which the annual compensation is commensurate with annual sales activities.

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General and administrative. General and administrative expenses include salaries, bonuses, benefits, and stock‑based compensation expense for our finance, human resources, and legal colleagues, the expense of travel, entertainment, and training for such personnel, professional fees for legal and accounting services, and costs of computer equipment and facilities used in general and administrative activities. Following the completion of the IPO, we continued to incur additional expenses as a result of operating as a public company, including costs to comply with the rules and regulations applicable to companies listed on a U.S. securities exchange and costs related to compliance and reporting obligations pursuant to the rules and regulations of the SEC. In addition, as a public company, we incur increased expenses in the areas of insurance, investor relations, and professional services. As a result, we expect the dollar amount of our general and administrative expenses to increase for the foreseeable future. We expect, however, that our general and administrative expenses will decrease as a percentage of our total revenues over time, although the percentage may fluctuate from period to period depending on fluctuations in our revenue and the timing and extent of our general and administrative expenses.

Deferred compensation plan. In August 2021, our board of directors approved an amendment to the DCP, which offered to certain active executives in the DCP a one‑time, short‑term election to reallocate a limited portion of their DCP holdings from phantom shares of the Company’s Class B Common Stock into other phantom investment funds. The offer to reallocate was subject to a proration mechanism which adjusted the aggregate elections to a maximum of 1,500,000 phantom shares of the Company’s Class B Common Stock. This one‑time reallocation opportunity was offered only to certain active executives (but not to Directors or Bentley family members) in order to encourage retention, as otherwise these executives could only have materially diversified their investments in Company equity (primarily held in the DCP) by voluntarily terminating employment to trigger DCP distributions. These executives in aggregate accordingly diversified 24% of their phantom shares of the Company’s Class B Common Stock. While DCP participants’ investments in phantom shares remain equity classified, as they will be settled in shares of Class B Common Stock upon eventual distribution, the amendment and elections resulted in a change to liability classification for the reallocated phantom investments, as they will be settled in cash upon eventual distribution. As a result, during the year ended December 31, 2021, we recognized a one‑time compensation charge of $90,721 to Deferred compensation plan expenses in the consolidated statement of operations to record the reallocated deferred compensation plan liabilities at their fair value. Deferred compensation plan liabilities are marked to market at the end of each reporting period, with changes in the liabilities recorded as an expense (income) to Deferred compensation plan in the consolidated statements of operations.

Amortization of purchased intangibles. Amortization of purchased intangibles includes the amortization of acquired non‑product related intangible assets, primarily customer relationships, trademarks, and non‑compete agreements recorded in connection with completed acquisitions.

Expenses associated with initial public offering. Expenses associated with IPO include certain non-recurring costs relating to our IPO, consisting of the payment of underwriting discounts and commissions applicable to the sale of shares by the selling stockholders, professional fees, and other expenses. We completed our IPO on September 25, 2020. These fees were expensed in the period incurred.

Interest expense, net

Interest expense, net primarily represents interest associated with the Credit Facility, the 2026 Notes, the 2027 Notes, amortization and write‑off of deferred debt issuance costs, and interest income from our investments in money market funds.

Other income (expense), net

Other income (expense), net primarily consists of foreign currency translation results derived primarily from U.S. Dollar denominated cash and cash equivalents, accounts receivable, and intercompany balances held by foreign subsidiaries with non‑U.S. Dollar functional currencies. Other income (expense), net also includes the fair value valuation result of our interest rate swap, payments related to our interest rate swap, the gain on the sale of 50% of our interest in our aircraft recorded during the year ended December 31, 2022, gain on extinguishment of debt, and changes in fair value of acquisition contingent consideration.

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(Provision) benefit for income taxes

(Provision) benefit for income taxes includes the aggregate consolidated income tax expense for U.S. domestic and foreign income taxes.

Loss from investments accounted for using the equity method, net of tax

Loss from investments accounted for using the equity method includes our proportional share of loss in our joint ventures.

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Results of Operations:

Our selected consolidated statements of operations data for each of the periods indicated are as follows:

Year Ended December 31,
202220212020
Revenues:
Subscriptions$960,220$812,807$679,273
Perpetual licenses43,37753,08057,382
Subscriptions and licenses1,003,597865,887736,655
Services95,48599,15964,889
Total revenues1,099,082965,046801,544
Cost of revenues:
Cost of subscriptions and licenses147,578124,32195,803
Cost of services89,43592,21871,352
Total cost of revenues237,013216,539167,155
Gross profit862,069748,507634,389
Operating expense (income):
Research and development257,856220,915185,515
Selling and marketing195,622162,240143,791
General and administrative174,647150,116113,274
Deferred compensation plan(15,782)95,046177
Amortization of purchased intangibles41,11425,60115,352
Expenses associated with initial public offering26,130
Total operating expenses653,457653,918484,239
Income from operations208,61294,589150,150
Interest expense, net(34,635)(11,221)(6,780)
Other income, net24,2989,96124,250
Income before income taxes198,27593,329167,620
(Provision) benefit for income taxes(21,283)3,448(38,625)
Loss from investments accounted for using the equity method, net of tax(2,212)(3,585)(2,474)
Net income174,78093,192126,521
Less: Net income attributable to participating securities(42)(9)(234)
Net income attributable to Class A and Class B common stockholders$174,738$93,183$126,287
Per share information:
Net income per share, basic$0.57$0.30$0.44
Net income per share, diluted$0.55$0.30$0.42
Weighted average shares, basic309,226,677305,711,345289,863,272
Weighted average shares, diluted331,765,158314,610,814299,371,129

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In reporting period‑over‑period results, we calculate the effects of foreign currency fluctuations and constant currency information by translating current period results using prior period average foreign currency exchange rates. Our definition of constant currency may differ from other companies reporting similarly named measures, and these constant currency performance measures should be viewed in addition to, and not as a substitute for, our operating performance measures calculated in accordance with U.S. GAAP.

Comparison of the Years Ended December 31, 2022 and 2021

Revenues

Comparison
Year EndedConstant
December 31,Currency
20222021Amount%%
Subscriptions$960,220$812,807$147,41318.1%24.3%
Perpetual licenses43,37753,080(9,703)(18.3%)(12.1%)
Subscriptions and licenses1,003,597865,887137,71015.9%22.1%
Services95,48599,159(3,674)(3.7%)0.4%
Total revenues$1,099,082$965,046$134,03613.9%19.8%

The increase in total revenues for the year ended December 31, 2022 was primarily driven by improvements in our business performance and the impact from our platform acquisitions in subscriptions revenues, partially offset by the overall negative foreign currency effects due to a stronger U.S. Dollar relative to our other currencies. Our business performance excludes the impact of our platform acquisitions and includes the impact from programmatic acquisitions, which generally are immaterial, individually and in the aggregate.

•Subscriptions. For the year ended December 31, 2022, the increase in subscriptions revenues was primarily driven by improvements in our business performance of approximately $54,500, or approximately $101,700 on a constant currency basis, and the impact from our platform acquisitions of approximately $92,900, or approximately $95,800 on a constant currency basis.

For the year ended December 31, 2022, the acquisition impact relates to our platform acquisitions of Seequent and Power Line Systems and is inclusive of their respective organic performance.

The improvements in business performance, on a constant currency basis, were primarily driven by expansion within our existing accounts, and growth of 2% attributable to new accounts exclusive of platform acquisitions, most notability smaller- and medium-sized accounts. Improvements in business performance for the year ended December 31, 2022 were led by our structural and civil engineering applications and our Enterprise Systems for project delivery.

•Perpetual licenses. For the year ended December 31, 2022, perpetual licenses revenues were impacted by a reduction in business performance of approximately $11,500, or approximately $8,300 on a constant currency basis, partially offset by our Seequent platform acquisition of approximately $1,800, or approximately $1,900 on a constant currency basis.

•Services. For the year ended December 31, 2022, services revenues were impacted by our Seequent and Power Line Systems platform acquisitions by approximately $1,300, or approximately $1,400 on a constant currency basis, partially offset by a reduction in business performance of approximately $5,000, or approximately $1,000 on a constant currency basis.

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For the year ended December 31, 2022, the reduction in business performance, on a constant currency basis, was impacted by the ongoing transition of historically classified services revenues into subscriptions revenues for accounts converting to our E365 subscription offering with embedded Success Services, partially offset by favorable contributions from Cohesive digital integrator services of approximately $3,800, or approximately $6,300 on a constant currency basis.

Revenues by Geographic Region

Revenue to external customers is attributed to individual countries based upon the location of the customer. Revenues by geographic region are as follows:

Comparison
Year EndedConstant
December 31,Currency
20222021Amount%%
Americas$584,794$483,087$101,70721.1%22.1%
EMEA312,804300,12312,6814.2%15.4%
APAC201,484181,83619,64810.8%21.1%
Total revenues$1,099,082$965,046$134,03613.9%19.8%

•Americas. For the year ended December 31, 2022, the increase in revenues from the Americas was primarily driven by an increase in subscriptions revenues from our Seequent and Power Line Systems platform acquisitions of approximately $56,700, or approximately $57,200 on a constant currency basis, and improvements in our business performance of approximately $43,300, or approximately $48,000 on a constant currency basis.

The improvements in business performance, on a constant currency basis, for the year ended December 31, 2022 were primarily due to expansion of our subscriptions revenues from existing accounts in the U.S.

•EMEA. For the year ended December 31, 2022, the increase in revenues from EMEA was primarily driven by the impact of our acquisitions of approximately $20,700, partially offset by a reduction in business performance of approximately $8,700. On a constant currency basis, revenues from EMEA increased due to improvements in our business performance of approximately $23,700 and the impact of our acquisitions of approximately $21,800. The increase from acquisitions was primarily due to an increase in subscriptions revenues from our Seequent and Power Line Systems platform acquisitions.

The improvements in business performance, on a constant currency basis, for the year ended December 31, 2022 were primarily due to expansion of our subscriptions revenues from existing accounts in Central Europe, the U.K., the Middle East, and Africa, partially offset by reductions in Russia.

•APAC. For the year ended December 31, 2022, the increase in revenues from APAC was primarily driven by improvements in our business performance of approximately $3,400, or approximately $20,700 on a constant currency basis, and an increase in subscriptions revenues from our Seequent and Power Line Systems platform acquisitions of approximately $15,500, or approximately $16,800 on a constant currency basis.

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The improvements in business performance for the year ended December 31, 2022 were primarily due to expansion of our recurring subscriptions revenues of approximately $13,600, or approximately $22,200 on a constant currency basis, in India, Australia, and Southeast Asia, partially offset by reductions of approximately $4,700, or approximately $3,700 on a constant currency basis, in China resulting from a confluence of events comprised of continued geopolitical challenges, the ongoing preference for locally developed, on premise software versus cloud-deployed, and additional impacts from COVID‑19, which may continue for the foreseeable future.

Cost of Revenues

Comparison
Year EndedConstant
December 31,Currency
20222021Amount%%
Cost of subscriptions and licenses$147,578$124,321$23,25718.7%24.5%
Cost of services89,43592,218(2,783)(3.0%)2.3%
Total cost of revenues$237,013$216,539$20,4749.5%15.1%

Cost of subscriptions and licenses. For the year ended December 31, 2022, on a constant currency basis, cost of subscriptions and licenses increased primarily due to an increase in headcount‑related costs of approximately $13,100, mainly due to our platform acquisition of Seequent and annual salary adjustments, an increase in channel partner compensation and royalties of approximately $5,500, an increase in cloud‑related costs of approximately $4,900, and an increase in amortization expense for software and technology of approximately $4,700.

Cost of services. For the year ended December 31, 2022, on a constant currency basis, cost of services increased primarily due to an increase in headcount-related costs of approximately $3,600, mainly due to digital integrator business acquisitions and annual salary adjustments, partially offset by a decrease in facilities costs of approximately $1,100.

Operating Expense (Income)

Comparison
Year EndedConstant
December 31,Currency
20222021Amount%%
Research and development$257,856$220,915$36,94116.7%22.1%
Selling and marketing195,622162,24033,38220.6%26.3%
General and administrative174,647150,11624,53116.3%19.7%
Deferred compensation plan(15,782)95,046(110,828)**
Amortization of purchased intangibles41,11425,60115,51360.6%67.2%
Total operating expenses$653,457$653,918$(461)(0.1%)4.2%

*Not meaningful

Research and development. For the year ended December 31, 2022, on a constant currency basis, research and development expenses increased primarily due to an increase in headcount-related costs of approximately $46,400. The increase in headcount-related costs was primarily comprised of approximately $33,600 of increases in salaries, mainly due to our platform acquisition of Seequent and annual salary adjustments, as well as an increase in stock-based compensation expense of approximately $8,100.

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Selling and marketing. For the year ended December 31, 2022, on a constant currency basis, selling and marketing expenses increased primarily due to an increase in headcount-related costs of approximately $34,200 and an increase in promotional costs of approximately $6,700. The increase in headcount-related costs was primarily comprised of an increase in salaries and variable compensation costs of approximately $25,800, mainly due to our platform acquisition of Seequent and annual salary adjustments, an increase in travel-related costs of approximately $5,100, and an increase in stock-based compensation expense of approximately $3,300.

General and administrative. For the year ended December 31, 2022, on a constant currency basis, general and administrative expenses increased primarily due to an increase in headcount-related costs of approximately $31,000 and an increase in facilities costs of approximately $3,300. The increase in headcount-related costs was primarily comprised of an increase in salaries costs of approximately $17,400, mainly due to our platform acquisition of Seequent and annual salary adjustments, and an increase in stock‑based compensation expense of approximately $14,300. Partially offsetting these increases were lower acquisition expenses of approximately $8,600, primarily due to expenses of $9,804 related to the acquisition of Power Line Systems for the year ended December 31, 2022 as compared to expenses of $16,557 related to the acquisition of Seequent for the year ended December 31, 2021.

Deferred compensation plan. For the year ended December 31, 2022, deferred compensation plan income was $15,782, which was attributable to the marked to market impact on deferred compensation plan liability balances period-over-period. For the year ended December 31, 2021, deferred compensation plan expense was $95,046. This amount was primarily attributable to a one‑time compensation charge of $90,721 as discussed in “—Key Factors Impacting Comparability and Performance,” and the marked to market impact on deferred compensation plan liability balances period-over-period.

Amortization of purchased intangibles. For the year ended December 31, 2022, on a constant currency basis, amortization of purchased intangibles increased primarily due to amortization from recently acquired purchased intangibles.

Interest Expense, Net

Year Ended
December 31,
20222021
Interest expense$(35,056)$(11,527)
Interest income421306
Interest expense, net$(34,635)$(11,221)
Year Ended
December 31,
20222021
Revolving loan facility$(15,798)$(3,448)
Term loans(7,413)(117)
Convertible senior notes, coupon interest(3,064)(1,899)
Amortization and write-off of deferred debt issuance costs(7,291)(5,955)
Other, net(1,069)198
Interest expense, net$(34,635)$(11,221)

For the year ended December 31, 2022, interest expense, net increased primarily due to a higher outstanding average balance combined with a higher average interest rate under the revolving loan facility, and interest expense on the term loan, which we entered into on December 22, 2021.

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Other Income, Net

Year Ended
December 31,
20222021
Gain (loss) from:
Change in fair value of interest rate swap$27,083$9,770
Foreign exchange (1)(9,901)827
Sale of aircraft2,029
Change in fair value of acquisition contingent consideration1,427(550)
Payments related to interest rate swap1,947(1,270)
Other income, net1,7131,184
Total other income, net$24,298$9,961

(1)Foreign exchange (loss) gain is primarily attributable to foreign currency translation derived mainly from U.S. Dollar denominated cash and cash equivalents, account receivables, customer deposits, and intercompany balances held by foreign subsidiaries. Intercompany finance transactions primarily denominated in U.S. Dollars resulted in unrealized foreign exchange losses of $7,369 and $779 for the years ended December 31, 2022 and 2021, respectively.

Provision (Benefit) for Income Taxes

Year Ended
December 31,
20222021
Income before income taxes$198,275$93,329
Provision (benefit) for income taxes$21,283$(3,448)
Effective tax rate10.7%(3.7)%

For the year ended December 31, 2022, the effective tax rate was higher as compared to the year ended December 31, 2021, primarily due to the 2021 effective tax rate impact, net of officer compensation limitation provisions, related to the 2021 compensation charge of $90,721 to Deferred compensation plan expenses to record reallocated deferred compensation plan liabilities at fair value. For the years ended December 31, 2022 and 2021, we recognized tax benefits of $20,501 and $14,890, respectively, associated with windfall tax benefits from stock‑based compensation, net of the impact from officer compensation limitation provisions.

Net Income

Year Ended
December 31,
20222021
Net income$174,780$93,192

For the year ended December 31, 2022, net income increased by $81,588, or 87.5%, compared to the year ended December 31, 2021. Net income as a percentage of total revenues was 15.9% and 9.7% for the year ended December 31, 2022 and 2021, respectively. The changes are due to the factors described above.

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Adjusted EBITDA and Adjusted Net Income

Year Ended
December 31,
20222021
Adjusted EBITDA$366,440$324,948
Adjusted Net Income$274,518$267,892

For the year ended December 31, 2022, Adjusted EBITDA increased by $41,492 compared to the year ended December 31, 2021. For the years ended December 31, 2022 and 2021, Adjusted EBITDA as a percentage of total revenues was 33.3% and 33.7%, respectively.

For the year ended December 31, 2022, Adjusted Net Income increased by $6,626 compared to the year ended December 31, 2021. For the years ended December 31, 2022 and 2021, Adjusted Net Income as a percentage of total revenues was 25.0% and 27.8%, respectively.

For additional information, including the limitations of using non‑GAAP financial measures, and reconciliations of the non‑GAAP financial measures to the most directly comparable financial measures stated in accordance with U.S. GAAP, see the section titled “—Non‑GAAP Financial Measures.”

Comparison of the Years Ended December 31, 2021 and 2020

Refer to Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations in our 2021 Annual Report on Form 10‑K.

Revenues

Comparison
Year EndedConstant
December 31,Currency
20212020Amount%%
Subscriptions$812,807$679,273$133,53419.7%17.6%
Perpetual licenses53,08057,382(4,302)(7.5%)(8.9%)
Subscriptions and licenses865,887736,655129,23217.5%15.6%
Services99,15964,88934,27052.8%48.6%
Total revenues$965,046$801,544$163,50220.4%18.2%

Revenues by Geographic Region

Revenue from external customers is attributed to individual countries based upon the location of the customer. Revenues by geographic region are as follows:

Comparison
Year EndedConstant
December 31,Currency
20212020Amount%%
Americas$483,087$395,746$87,34122.1%21.4%
EMEA300,123254,03646,08718.1%14.2%
APAC181,836151,76230,07419.8%16.8%
Total revenues$965,046$801,544$163,50220.4%18.2%

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Cost of Revenues

Comparison
Year EndedConstant
December 31,Currency
20212020Amount%%
Cost of subscriptions and licenses$124,321$95,803$28,51829.8%27.3%
Cost of services92,21871,35220,86629.2%24.4%
Total cost of revenues$216,539$167,155$49,38429.5%26.1%

Operating Expenses

Comparison
Year EndedConstant
December 31,Currency
20212020Amount%%
Research and development$220,915$185,515$35,40019.1%16.5%
Selling and marketing162,240143,79118,44912.8%10.1%
General and administrative150,116113,27436,84232.5%31.1%
Deferred compensation plan95,04617794,869**
Amortization of purchased intangibles25,60115,35210,24966.8%61.3%
Expenses associated with initial public offering26,130(26,130)**
Total operating expenses$653,918$484,239$169,67935.0%32.8%

*Not meaningful

Interest Expense, Net

Year Ended
December 31,
20212020
Interest expense$(11,527)$(7,217)
Interest income306437
Interest expense, net$(11,221)$(6,780)
Year Ended
December 31,
20212020
Revolving loan facility$(3,448)$(5,680)
Term loans(117)(502)
Convertible senior notes, coupon interest(1,899)
Amortization and write-off of deferred debt issuance costs(5,955)(985)
Other, net198387
Interest expense, net$(11,221)$(6,780)

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Other Income, Net

Year Ended
December 31,
20212020
Gain (loss) from:
Change in fair value of interest rate swap$9,770$347
Foreign exchange (1)82722,919
Change in fair value of acquisition contingent consideration(550)1,340
Payments related to interest rate swap(1,270)(696)
Other income, net1,184340
Total other income, net$9,961$24,250

(1)Foreign exchange gain is primarily attributable to foreign currency translation derived mainly from U.S. Dollar denominated cash and cash equivalents, account receivables, customer deposits, and intercompany balances held by foreign subsidiaries. Intercompany finance transactions primarily denominated in U.S. Dollars resulted in unrealized foreign exchange (losses) gains of $(779) and $22,310 for the years ended December 31, 2021 and 2020, respectively.

(Benefit) Provision for Income Taxes

Year Ended
December 31,
20212020
Income before income taxes$93,329$167,620
(Benefit) provision for income taxes$(3,448)$38,625
Effective tax rate(3.7)%23.0%

Net Income

Year Ended
December 31,
20212020
Net income$93,192$126,521

Adjusted EBITDA and Adjusted Net Income

Year Ended
December 31,
20212020
Adjusted EBITDA$324,948$266,376
Adjusted Net Income$267,892$193,334

For additional information, including the limitations of using non‑GAAP financial measures, and reconciliations of the non‑GAAP financial measures to the most directly comparable financial measures stated in accordance with U.S. GAAP, see the section titled “—Non‑GAAP Financial Measures.”

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Liquidity and Capital Resources:

Our primary source of operating cash is from the sale of subscriptions, perpetual licenses, and services. Our primary use of cash is payment of our operating costs, which consist primarily of headcount‑related costs. In addition to operating expenses, we also use cash to service our debt obligations, to pay quarterly dividends, to repurchase our Class B Common Stock and subordinated indebtedness (discussed further below), and for capital expenditures in support of our operations. We also use cash to fund our acquisitions of software assets and businesses, and other investment activities, including our iTwin Ventures initiative for which, over a period of approximately 5 years, we expect to invest up to $100 million of corporate venture capital funding for seed, early, and growth stage technology companies with promising and emerging opportunities for infrastructure digital twin solutions strategically relevant to our business. In connection with the acquisition of Power Line Systems in January 2022, we used available cash and borrowings under our Credit Facility to fund the transaction. In connection with the acquisition of Seequent in June 2021, we used available cash, including a portion of the net proceeds from the 2026 Notes, and borrowings under our Credit Facility to fund the cash component of the transaction. As described further below, we used $25,875 of the net proceeds from the sale of the 2027 Notes to pay the premiums of the capped call options, and $536,062 to repay outstanding indebtedness under the Credit Facility and to pay related fees and expenses. We used $25,530 of the net proceeds from the sale of the 2026 Notes to pay the premiums of the capped call options, and approximately $250,500 to repay outstanding indebtedness under the Credit Facility and to pay related fees and expenses. We used the remainder of the net proceeds from the sale of the 2026 Notes for general corporate purposes and towards funding certain acquisitions, including Seequent.

On May 11, 2022, we announced that our board of directors approved the Repurchase Program authorizing us to repurchase up to $200,000 of our Class B Common Stock through June 30, 2024. On December 14, 2022, our board of directors amended the Repurchase Program to allow us also to repurchase its outstanding convertible senior notes. This additional authorization did not increase the overall dollar limit of the Repurchase Program. The shares and notes proposed to be acquired in the Repurchase Program may be repurchased from time to time in open market transactions, through privately negotiated transactions, or by other means in accordance with federal securities laws. We intend to fund repurchases from available working capital and cash provided by operating activities. The timing, as well as the number and value of shares and/or notes repurchased under the Repurchase Program, will be determined at our discretion and will depend on a variety of factors, including management’s assessment of the intrinsic value of our shares, the market price of our Class B Common Stock and outstanding notes, general market and economic conditions, available liquidity, compliance with our debt and other agreements, and applicable legal requirements. The exact number of shares and/or notes to be repurchased by us is not guaranteed, and the Repurchase Program may be suspended, modified, or discontinued at any time without prior notice. For the year ended December 31, 2022, we repurchased 896,126 shares for $28,250, and $2,170 aggregate principal amount of our outstanding 2026 Notes for $1,998.

Additionally, during the second, third, and fourth quarters of 2022, we exercised our right to require that certain equity awardees receive gross quantities of shares of our Class B Common Stock, most meaningfully for the issuance of shares in connection with our Executive Bonus Plan incentive compensation and distributions from the DCP, and promptly reimburse to us the cash required for their tax withholding amounts. Historically, these shares were issuable on a net basis, holding back shares in consideration of remitting withholding taxes on behalf of equity awardees, thereby requiring us to remit cash for the tax withholdings. We will continue to evaluate whether share awards will be required to be received by awardees on a gross basis, or if net settlement may be elected by awardees.

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Our cash and cash equivalent balances are concentrated in a few locations around the world, with substantial amounts held outside of the U.S. As of December 31, 2022 and 2021, 95% and 48%, respectively, of our total cash and cash equivalents were located outside of the U.S. During the year ended December 31, 2022, we repatriated $150,000 of undistributed previously taxed earnings generated by our foreign subsidiaries to the U.S. The repatriations were used to fund the acquisition of Power Line Systems. We have provided for any applicable income taxes associated with current year distributions, as well as any earnings that are expected to be distributed in the future, in the calculation of the income tax provision. No additional provision has been made for U.S. and non-U.S. income taxes on the undistributed earnings of subsidiaries as that cash is expected to be indefinitely reinvested. We expect to meet our U.S. liquidity needs through ongoing cash flows or external borrowings including available liquidity under the Credit Facility. We regularly review our capital structure and consider a variety of potential financing alternatives and planning strategies to ensure that we have the proper liquidity available in the locations in which it is needed and to fund our operations and growth investments with cash that has not been permanently reinvested outside the U.S.

We believe that existing cash and cash equivalent balances, together with cash generated from operations, and liquidity under the Credit Facility, will be sufficient to meet our domestic and international working capital and capital expenditure requirements through the next twelve months. However, our future capital requirements may be materially different than those currently planned in our budgeting and forecasting activities and depend on many factors, including our strategy of regularly acquiring and integrating specialized infrastructure engineering software businesses, our rate of revenue growth, the timing and extent of spending on research and development, the expansion of our sales and marketing activities, the timing of new product introductions, market acceptance of our products, competitive factors, our discretionary payments of dividends or repurchases of our Class B Common Stock, currency fluctuations, and overall economic conditions, globally. To the extent that current and anticipated future sources of liquidity are insufficient to fund our future business activities and requirements, we may be required to seek additional equity or debt financing. The sale of additional equity would result in additional dilution to our stockholders, while the incurrence of debt financing, including convertible debt, would result in debt service obligations. Such debt instruments also could introduce covenants that might restrict our operations. We cannot provide assurance that we could obtain additional financing on favorable terms or at all.

Cash and cash equivalents

We consider all highly liquid investments with an original maturity of three months or less at the date of purchase to be cash equivalents. Our cash and cash equivalents consisted of cash held in checking accounts and money market funds maintained at various financial institutions. Our domestic and foreign holdings of cash and cash equivalents are as follows:

December 31,
20222021
Cash and cash equivalents held domestically$3,883$170,267
Cash and cash equivalents held by foreign subsidiaries67,801159,070
Total cash and cash equivalents$71,684$329,337

The amount of cash and cash equivalents held by foreign subsidiaries is subject to translation adjustments caused by changes in foreign currency exchange rates as of the end of each respective reporting period, the offset to which is recorded in Accumulated other comprehensive loss on our consolidated balance sheets.

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Bank Credit Facility

We are party to a Credit Agreement dated December 19, 2017, (as amended from time to time) which provides for an $850,000 senior secured revolving loan facility that matures on November 15, 2025. Debt issuance costs are amortized to interest expense through the maturity date.

When we amended the Credit Facility on January 25, 2021, to increase the senior secured revolving loan facility and extend the maturity date, we performed an extinguishment versus modification assessment on a lender‑by‑lender basis resulting in the write‑off of unamortized debt issuance costs of $353 and the capitalization of fees paid to lenders and third parties of $3,577.

The Credit Facility also provides up to $50,000 of letters of credit and other borrowings subject to availability, including an $85,000 U.S. Dollar swingline sub‑facility and a $200,000 incremental “accordion” sub‑facility. We had $150 of letters of credit and surety bonds outstanding as of December 31, 2022 and 2021. As of December 31, 2022 and 2021, we had $504,253 and $849,850, respectively, available under the Credit Facility.

Under the Credit Facility, we may make either Euro currency or non‑Euro currency interest rate elections. Interest on the Euro currency borrowings bear a base interest rate of LIBOR plus a spread ranging from 125 basis points (“bps”) to 225 bps as determined by our net leverage ratio. Under the non‑Euro currency elections, Credit Facility borrowings bear a base interest rate of the highest of (i) the prime rate, (ii) the overnight bank funding effective rate plus 50 bps, or (iii) LIBOR plus 100 bps, plus a spread ranging from 25 bps to 125 bps as determined by our net leverage ratio. In addition, a commitment fee for the unused Credit Facility ranges from 20 bps to 30 bps as determined by our net leverage ratio.

Borrowings under the Credit Facility are guaranteed by all of our material first tier domestic subsidiaries and are secured by a first priority security interest in substantially all of our and the guarantors’ U.S. assets and 65% of the stock of their directly owned foreign subsidiaries.

The agreement governing the Credit Facility contains customary positive and negative covenants, including restrictions on our ability to pay dividends and make other restricted payments, as well as events of default, including, without limitation, payment defaults, breaches of representations and warranties, covenants defaults, cross-defaults to certain other indebtedness in excess of $50,000, certain events of bankruptcy and insolvency, judgment defaults in excess of $10,000, failure of any security document supporting the Credit Facility to be in full force and effect, and a change of control. The Credit Facility also contains customary financial covenants, including maximum net leverage ratios. As of December 31, 2022 and 2021, we were in compliance with all covenants in our Credit Facility.

Voluntary prepayments of amounts outstanding under the Credit Facility, in whole or in part, are permitted at any time, so long as we give notice as required by the Credit Facility. However, if prepayment is made with respect to a LIBOR‑based loan and the prepayment is made on a date other than an interest payment date, we must pay customary breakage costs.

Term Loans. On December 22, 2021, we amended the Credit Facility to provide for a $200,000 senior secured term loan with a maturity of November 15, 2025 (the “2021 Term Loan”) and included certain other conforming amendments. The 2021 Term Loan requires principal repayment at the end of each calendar quarter. Beginning with March 31, 2022 and ending with December 31, 2023, we are required to repay $1,250 per quarter. Beginning with March 31, 2024 and ending with the last such date prior to the maturity date, we are required to repay $2,500 per quarter. We incurred $540 of debt issuance costs related to the 2021 Term Loan. We used borrowings under the 2021 Term Loan to pay down borrowings under the swingline sub‑facility and revolving loan facility under the Credit Facility.

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Under the 2021 Term Loan, we may make either Euro currency or non-Euro currency interest rate elections. Interest on the Euro currency borrowings bear a base interest rate of LIBOR, plus a spread ranging from 100 bps to 200 bps as determined by our net leverage ratio. Under the non-Euro currency elections, the 2021 Term Loan bears a base interest rate of the highest of (i) the prime rate, (ii) the overnight bank funding effective rate plus 50 bps, or (iii) LIBOR plus 100 bps, plus a spread ranging from 0 bps to 100 bps as determined by our net leverage ratio.

Prior to the IPO, on September 2, 2020, we amended the Credit Facility to incur a term loan of $125,000 (the “2020 Term Loan”) with a maturity of December 18, 2022. We used the proceeds from the 2020 Term Loan and borrowings under the revolving loan facility under the Credit Facility to pay a special dividend declared by our board of directors on August 28, 2020. We incurred $432 of debt issuance costs related to the 2020 Term Loan. In November 2020, we used a portion of the net proceeds from our follow‑on public offering to repay the 2020 Term Loan. See Notes 10 and 13 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K.

Bank Credit Facility Interest. The revolving loan facility and term loans weighted average interest rate was 3.84%, 2.03%, and 1.92% for the years ended December 31, 2022, 2021, and 2020, respectively.

Interest rate risk associated with the Credit Facility is managed through an interest rate swap which we executed on March 31, 2020. The interest rate swap has an effective date of April 2, 2020 and a termination date of April 2, 2030. Under the terms of the interest rate swap, we fixed our LIBOR borrowing rate at 0.73% on a notional amount of $200,000.

Convertible Senior Notes

2027 Notes. On June 28, 2021, we completed a private offering of $575,000 of 0.375% convertible senior notes due 2027. The 2027 Notes were issued pursuant to an indenture, dated as of June 28, 2021, between the Company and Wilmington Trust, National Association, as trustee (the “2027 Trustee”) (the “2027 Indenture”). Interest will accrue from June 28, 2021 and will be payable semi‑annually in arrears in cash on January 1 and July 1 of each year, with the first payment due on January 1, 2022. The 2027 Notes will mature on July 1, 2027, unless earlier converted, redeemed or repurchased. We incurred $15,065 of expenses in connection with the 2027 Notes offering consisting of the payment of initial purchasers’ discounts and commissions, professional fees, and other expenses (“transaction costs”). We used $25,875 of the net proceeds from the sale of the 2027 Notes to pay the premiums of the capped call options described further below, and $536,062 to repay outstanding indebtedness under the Credit Facility and to pay related fees and expenses.

Prior to April 1, 2027, the 2027 Notes will be convertible at the option of the holder only under the following circumstances: (1) during any calendar quarter (and only during such quarter) commencing after the calendar quarter ending on September 30, 2021, if the last reported sale price per share of our Class B Common Stock exceeds 130% of the conversion price for each of at least 20 trading days, whether or not consecutive, during the 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding calendar quarter; (2) during the five consecutive business days immediately after any ten consecutive trading day period (such ten consecutive trading day period, the “measurement period”) in which the trading price per $1 principal amount of 2027 Notes for each trading day of the measurement period was less than 98% of the product of the last reported sale price per share of our Class B Common Stock on such trading day and the conversion rate on such trading day; (3) upon the occurrence of certain corporate events or distributions on our Class B Common Stock, as described in the 2027 Indenture; and (4) if we call the 2027 Notes for redemption. On or after April 1, 2027 until 5:00 p.m., New York City time, on the second scheduled trading day immediately before the maturity date, the 2027 Notes will be convertible at the option of the holder at any time.

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We will settle conversions by paying or delivering, as applicable, cash, shares of our Class B Common Stock or a combination of cash and shares of our Class B Common Stock, at our election, based on the applicable conversion rate. The initial conversion rate is 12.0153 shares of our Class B Common Stock per $1 principal amount of 2027 Notes, which represents an initial conversion price of approximately $83.23 per share, and is subject to adjustment as described in the 2027 Indenture. If a “make-whole fundamental change” (as defined in the 2027 Indenture) occurs, then we will, in certain circumstances, increase the conversion rate for a specified period of time.

We will have the option to redeem the 2027 Notes in whole or in part at any time on or after July 5, 2024 and on or before the 40th scheduled trading day immediately before the maturity date if the last reported sale price per share of our Class B common stock exceeds 130% of the conversion price on (1) each of at least 20 trading days, whether or not consecutive, during any 30 consecutive trading days ending on, and including, the trading day immediately before the date we send the related redemption notice; and (2) the trading day immediately before the date we send such notice. The redemption price will be equal to the principal amount of the 2027 Notes to be redeemed, plus accrued and unpaid interest, if any, to, but excluding, the redemption date.

Upon a fundamental change (as defined in the 2027 Indenture), holders may, subject to certain exceptions, require us to purchase their 2027 Notes in whole or in part for cash at a price equal to the principal amount of the 2027 Notes to be purchased, plus accrued and unpaid interest, if any, to, but excluding, the fundamental change repurchase date (as defined in the 2027 Indenture). In addition, upon a Make‑Whole Fundamental Change (as defined in the 2027 Indenture), we will, under certain circumstances, increase the applicable conversion rate for a holder that elects to convert its 2027 Notes in connection with such Make‑Whole Fundamental Change. No adjustment to the conversion rate will be made if the stock price in such Make‑Whole Fundamental Change is either less than $61.65 per share or greater than $325.00 per share. We will not increase the conversion rate to an amount that exceeds 16.2206 shares per $1 principal amount of 2027 Notes, subject to adjustment. The 2027 Indenture also contains a customary merger covenant.

Under the 2027 Indenture, the 2027 Notes may be accelerated upon the occurrence of certain customary events of default. If certain bankruptcy and insolvency‑related events of default with respect to us occur, the principal of, and accrued and unpaid interest on, all of the then outstanding 2027 Notes shall automatically become due and payable. If any other event of default occurs and is continuing, the 2027 Trustee by notice to us, or the holders of the 2027 Notes of at least 25% in principal amount of the outstanding 2027 Notes by notice to us and the 2027 Trustee, may declare the principal of, and accrued and unpaid interest on, all of the then outstanding 2027 Notes to be due and payable. Notwithstanding the foregoing, the 2027 Indenture provides that, to the extent we elect, the sole remedy for an event of default relating to certain failures by us to comply with reporting covenant in the 2027 Indenture consists exclusively of the right to receive additional interest on the 2027 Notes.

The 2027 Notes were accounted for as debt, with no bifurcation of the embedded conversion feature. Transaction costs were recorded as a direct deduction from the related debt liability in the consolidated balance sheets and are amortized to interest expense over the term of the 2027 Notes. The effective interest rate for the 2027 Notes is 0.864%.

As of December 31, 2022, none of the conditions of the 2027 Notes to early convert has been met.

The 2027 Notes are our senior, unsecured obligations that rank senior in right of payment to our future indebtedness that is expressly subordinated to the 2027 Notes, rank equally in right of payment with our existing and future senior unsecured indebtedness that is not so subordinated (including our 2026 Notes), effectively subordinated to our existing and future secured indebtedness (including obligations under our senior secured credit facilities), to the extent of the value of the collateral securing such indebtedness, and structurally subordinated to all existing and future indebtedness and other liabilities (including trade payables and preferred equity (to the extent we are not a holder thereof)) of our subsidiaries. The 2027 Notes contain both affirmative and negative covenants. As of December 31, 2022 and 2021, we were in compliance with all covenants in the 2027 Notes.

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Capped Call Options. In connection with the pricing of the 2027 Notes, we entered into capped call options with certain of the initial purchasers or their respective affiliates and certain other financial institutions. We incurred $50 of expenses in connection with the capped call options. The capped call options are expected to reduce potential dilution to our Class B Common Stock upon any conversion of 2027 Notes and/or offset any cash payments we are required to make in excess of the principal amount of converted notes, as the case may be, with such reduction and/or offset subject to a cap. The cap price of the capped call options is initially $95.5575 per share, which represents a premium of 55% above the last reported sale price per share of our Class B Common Stock on the Nasdaq Global Select Market on June 23, 2021 and is subject to customary adjustments under the terms of the capped call options.

The capped call options were entered into in conjunction with the issuance of the 2027 Notes, however, they are legally separate agreements that can be separately exercised, with the receipt of shares under the capped call options having no effect on the 2027 Notes, and are legally detachable. As the capped call options are both legally detachable and separately exercisable from the 2027 Notes, we account for the capped call options separately from the 2027 Notes. The capped call options are indexed to our own common stock and classified in stockholders’ equity. As such, the premiums paid for the capped call options have been included as a net reduction to Additional paid-in capital in the consolidated balance sheet.

2026 Notes. On January 26, 2021, we completed a private offering of $690,000 of 0.125% convertible senior notes due 2026. The 2026 Notes were issued pursuant to an indenture, dated as of January 26, 2021, between the Company and Wilmington Trust, National Association, as trustee (the “2026 Trustee”) (the “2026 Indenture”). Interest will accrue from January 26, 2021 and will be payable semi‑annually in arrears in cash on January 15 and July 15 of each year, with the first payment due on July 15, 2021. The 2026 Notes will mature on January 15, 2026, unless earlier converted, redeemed or repurchased. We incurred $18,055 of expenses in connection with the 2026 Notes offering consisting of transaction costs. We used $25,530 of the net proceeds from the sale of the 2026 Notes to pay the premiums of the capped call options described further below, and approximately $250,500 to repay outstanding indebtedness under the Credit Facility and to pay related fees and expenses. We used the remainder of the net proceeds from the sale of the 2026 Notes for general corporate purposes and towards funding certain acquisitions, including Seequent.

During the fourth quarter of 2022, we paid $1,998 in cash to repurchase $2,170 aggregate principal amount of our outstanding 2026 Notes through open market transactions resulting in an insignificant gain, which was recorded in Other income, net in the consolidated statement of operations for the year ended December 31, 2022. The 2026 Notes were repurchased under our Repurchase Program authorization.

Prior to October 15, 2025, the 2026 Notes will be convertible at the option of the holder only under the following circumstances: (1) during any calendar quarter (and only during such quarter) commencing after the calendar quarter ending on June 30, 2021, if the last reported sale price per share of our Class B Common Stock exceeds 130% of the conversion price for each of at least 20 trading days, whether or not consecutive, during the 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding calendar quarter; (2) during the five consecutive business days immediately after any ten consecutive trading day period (such ten consecutive trading day period, the “measurement period”) in which the trading price per $1 principal amount of 2026 Notes for each trading day of the measurement period was less than 98% of the product of the last reported sale price per share of our Class B Common Stock on such trading day and the conversion rate on such trading day; (3) upon the occurrence of certain corporate events or distributions on our Class B Common Stock, as described in the 2026 Indenture; and (4) if we call the 2026 Notes for redemption. On or after October 15, 2025 until 5:00 p.m., New York City time, on the second scheduled trading day immediately before the maturity date, the 2026 Notes will be convertible at the option of the holder at any time.

We will settle conversions by paying or delivering, as applicable, cash, shares of our Class B Common Stock or a combination of cash and shares of our Class B Common Stock, at our election, based on the applicable conversion rate. The initial conversion rate is 15.5925 shares of our Class B Common Stock per $1 principal amount of 2026 Notes, which represents an initial conversion price of approximately $64.13 per share, and is subject to adjustment as described in the 2026 Indenture. If a “make-whole fundamental change” (as defined in the 2026 Indenture) occurs, then we will, in certain circumstances, increase the conversion rate for a specified period of time.

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We will have the option to redeem the 2026 Notes in whole or in part at any time on or after January 20, 2024 and on or before the 40th scheduled trading day immediately before the maturity date if the last reported sale price per share of our Class B common stock exceeds 130% of the conversion price on (1) each of at least 20 trading days, whether or not consecutive, during any 30 consecutive trading days ending on, and including, the trading day immediately before the date we send the related redemption notice; and (2) the trading day immediately before the date we send such notice. The redemption price will be equal to the principal amount of the 2026 Notes to be redeemed, plus accrued and unpaid interest, if any, to, but excluding, the redemption date.

Upon a fundamental change (as defined in the 2026 Indenture), holders may, subject to certain exceptions, require us to purchase their 2026 Notes in whole or in part for cash at a price equal to the principal amount of the 2026 Notes to be purchased, plus accrued and unpaid interest, if any, to, but excluding, the fundamental change repurchase date (as defined in the 2026 Indenture). In addition, upon a Make‑Whole Fundamental Change (as defined in the 2026 Indenture), we will, under certain circumstances, increase the applicable conversion rate for a holder that elects to convert its 2026 Notes in connection with such Make‑Whole Fundamental Change. No adjustment to the conversion rate will be made if the stock price in such Make‑Whole Fundamental Change is either less than $44.23 per share or greater than $210.00 per share. We will not increase the conversion rate to an amount that exceeds 22.6090 shares per $1 principal amount of 2026 Notes, subject to adjustment. The 2026 Indenture also contains a customary merger covenant.

Under the 2026 Indenture, the 2026 Notes may be accelerated upon the occurrence of certain customary events of default. If certain bankruptcy and insolvency‑related events of default with respect to us occur, the principal of, and accrued and unpaid interest on, all of the then outstanding 2026 Notes shall automatically become due and payable. If any other event of default occurs and is continuing, the 2026 Trustee by notice to us, or the holders of the 2026 Notes of at least 25% in principal amount of the outstanding 2026 Notes by notice to us and the 2026 Trustee, may declare the principal of, and accrued and unpaid interest on, all of the then outstanding 2026 Notes to be due and payable. Notwithstanding the foregoing, the 2026 Indenture provides that, to the extent we elect, the sole remedy for an event of default relating to certain failures by us to comply with reporting covenant in the 2026 Indenture consists exclusively of the right to receive additional interest on the 2026 Notes.

The 2026 Notes were accounted for as debt, with no bifurcation of the embedded conversion feature. Transaction costs were recorded as a direct deduction from the related debt liability in the consolidated balance sheets and are amortized to interest expense over the term of the 2026 Notes. The effective interest rate for the 2026 Notes is 0.658%.

As of December 31, 2022, none of the conditions of the 2026 Notes to early convert has been met.

The 2026 Notes are our senior, unsecured obligations that rank senior in right of payment to our future indebtedness that is expressly subordinated to the 2026 Notes, rank equally in right of payment with our existing and future senior unsecured indebtedness that is not so subordinated (including our 2027 Notes, see the section titled “—2027 Notes” below), effectively subordinated to our existing and future secured indebtedness (including obligations under our senior secured credit facilities), to the extent of the value of the collateral securing such indebtedness, and structurally subordinated to all existing and future indebtedness and other liabilities (including trade payables and preferred equity (to the extent we are not a holder thereof)) of our subsidiaries. The 2026 Notes contain both affirmative and negative covenants. As of December 31, 2022 and 2021, we were in compliance with all covenants in the 2026 Notes.

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Capped Call Options. In connection with the pricing of the 2026 Notes, we entered into capped call options with certain of the initial purchasers or their respective affiliates and certain other financial institutions. We incurred $150 of expenses in connection with the capped call options. The capped call options are expected to reduce potential dilution to our Class B Common Stock upon any conversion of 2026 Notes and/or offset any cash payments we are required to make in excess of the principal amount of converted notes, as the case may be, with such reduction and/or offset subject to a cap. The cap price of the capped call options is initially $72.9795 per share, which represents a premium of 65% above the last reported sale price per share of our Class B Common Stock on the Nasdaq Global Select Market on January 21, 2021 and is subject to customary adjustments under the terms of the capped call options.

The capped call options were entered into in conjunction with the issuance of the 2026 Notes, however, they are legally separate agreements that can be separately exercised, with the receipt of shares under the capped call options having no effect on the 2026 Notes, and are legally detachable. As the capped call options are both legally detachable and separately exercisable from the 2026 Notes, we account for the capped call options separately from the 2026 Notes. The capped call options are indexed to our own common stock and classified in stockholders’ equity. As such, the premiums paid for the capped call options have been included as a net reduction to Additional paid-in capital in the consolidated balance sheet.

Comparison of the Year Ended December 31, 2022 and 2021

Our cash flow activities for the years ended December 31, 2022 and 2021 consist of the following:

Year Ended December 31,
20222021
Net Cash Provided By (Used In):
Operating activities$274,324$288,024
Investing activities(770,127)(1,056,603)
Financing activities243,034982,582

Operating activities

Net cash provided by operating activities was $274,324 for the year ended December 31, 2022. Compared to the prior year, net cash provided by operating activities was lower by $13,700 due to a net decrease in non‑cash adjustments of $64,090 and a net decrease in net cash flows from the change in operating assets and liabilities of $31,198, partially offset by an increase in net income of $81,588. Both the increase in net income and the net decrease in non‑cash adjustments were impacted by the one‑time, non‑cash compensation charge of $90,721 to Deferred compensation plan expenses during the year ended December 31, 2021 to record reallocated deferred compensation plan liabilities at fair value as previously discussed. The net decrease in cash flows from the change in operating assets and liabilities was primarily due to the timing of renewals and associated billings of certain annual contracts, and increased interest payments.

For the year ended December 31, 2021, net cash provided by operating activities was $288,024 due to net income of $93,192 increased by $178,726 of non‑cash adjustments and $16,106 from changes in operating assets and liabilities.

Investing activities

Net cash used in investing activities was $770,127 for the year ended December 31, 2022 primarily due to $743,007 in acquisition related payments, net of cash acquired, to complete six acquisitions.

For the year ended December 31, 2021, net cash used in investing activities was $1,056,603 primarily due to $1,034,983 in acquisition related payments, net of cash acquired, to complete 13 acquisitions.

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Financing activities

Net cash provided by financing activities was $243,034 for the year ended December 31, 2022 primarily due to an increase in net borrowings under the Credit Facility of $340,598, partially offset by net payments for shares acquired of $71,811, including shares repurchased under the Repurchase Program, and payments of dividends of $34,493.

For the year ended December 31, 2021, net cash provided by financing activities was $982,582 primarily due to the net proceeds from the convertible senior notes of $1,233,377, partially offset by net payments for shares acquired of $120,539 and the purchase of capped call options of $51,605.

Contractual Obligations and Other Commitments:

As of December 31, 2022, our future contractual obligations were related to debt (see Note 10), leases (see Note 8), purchase obligations (see Note 18), deferred compensation plan liabilities (see Note 12), and contingent and non‑contingent consideration from acquisitions (see Note 4). For information about those obligations, see the above referenced notes to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K, which are incorporated by reference into this section. As of December 31, 2022, our purchase obligations were $14,981, which is expected to be paid within one year. Purchase obligations include the non‑cancelable future cash purchase commitment for services related to the provisioning of our hosted software solutions. Our purchase obligations are in addition to amounts included in current liabilities and prepaid expenses in our consolidated balance sheet.

Critical Accounting Policies and Estimates:

Our consolidated financial statements are prepared in conformity with U.S. GAAP. In preparing our consolidated financial statements, we make assumptions, judgments, and estimates that can have a significant impact on amounts reported in the consolidated financial statements. We base our assumptions, judgments, and estimates on historical experience and various other factors that we believe to be reasonable under the circumstances. Actual results could differ materially from these estimates under different assumptions or conditions. We regularly reevaluate our assumptions, judgments, and estimates. Our significant accounting policies are described in Note 1 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K.

An accounting policy is deemed to be critical if it requires an accounting estimate to be made based on assumptions about matters that are highly uncertain at the time the estimate is made, if different estimates reasonably could have been used, or if changes in the estimate that are reasonably possible could materially impact the financial statements. We believe that the following critical accounting policies affect the more significant judgments and estimates used in the preparation of our consolidated financial statements.

Revenue recognition. For a full description of our revenue accounting policy, see Note 1 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K. We generate revenues from subscriptions, perpetual licenses, and services.

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Our contracts with customers may include promises to transfer licenses (perpetual or term‑based), maintenance, and services to a user. Judgment is required to determine if the promises are separate performance obligations, and if so, the allocation of the transaction price to each performance obligation. When an arrangement includes multiple performance obligations which are concurrently delivered and have the same pattern of transfer to the customer, we account for those performance obligations as a single performance obligation. For contracts with more than one performance obligation, the transaction price is allocated among the performance obligations in an amount that depicts the relative SSP of each obligation. Judgment is required to determine the SSP for each distinct performance obligation. In instances where SSP is not directly observable, such as when we do not sell the product or service separately, we determine the SSP using information that may include market conditions and other observable inputs. We use a range of amounts to estimate SSP when we sell each of the products and services separately and need to determine whether there is a discount that should be allocated based on the relative SSP of the various products and services.

Our SELECT agreement provides users with perpetual licenses a right to exchange software for other eligible perpetual licenses on an annual basis upon renewal. We refer to this option as portfolio balancing and concluded that the portfolio balancing feature represents a material right resulting in the deferral of the associated revenue. Judgment is required to estimate the percentage of users who may elect to portfolio balance and considers inputs such as historical user elections. This feature is available once per term and must be exercised prior to the respective renewal term. We recognize the associated revenue upon election or when the portfolio balancing right expires. This right is included in the initial and subsequent renewal terms and we reestablish the revenue deferral for the material right upon the beginning of the renewal term. Portfolio balancing exchange rights are included in Deferred revenues in the consolidated balance sheets.

Business combinations. We allocate the fair value of the consideration transferred to the assets acquired and liabilities assumed, including trademarks, customer relationships, in‑process research and development, and acquired software and technology, based on their estimated fair values at the acquisition date. Any residual purchase price is recorded as goodwill. The purchase price allocation requires us to make significant estimates and assumptions, especially at the acquisition date, with respect to intangible assets.

Although we believe the assumptions and estimates we have made are reasonable, they are based in part on historical experience and information obtained from the management of the acquired companies and are inherently uncertain. Examples of critical estimates used in valuing certain of the intangible assets we have acquired or may acquire in the future include but are not limited to:

•future expected cash flows from total revenues and acquired developed technologies;

•the acquired company’s trade name and customer relationships as well as assumptions about the period of time the acquired trade name and customer relationships will continue to be used in our product portfolio;

•expected costs to develop the in-process research and development into commercially viable software and estimated cash flows from the projects when completed; and

•discount rates used to determine the present value of estimated future cash flows.

These estimates are inherently uncertain and unpredictable, and if different estimates were used the purchase price for the acquisition could be allocated to the acquired assets and liabilities differently from the allocation that we have made. In addition, unanticipated events and circumstances may occur, which may affect the accuracy or validity of such estimates, and, if such events occur, we may be required to record a charge against the value ascribed to an acquired asset or an increase in the amounts recorded for assumed liabilities.

Goodwill and other intangible assets. Intangible assets arise from acquisitions and principally consist of goodwill, trademarks, customer relationships, in‑process research and development, and acquired software and technology. Intangible assets, other than goodwill and in‑process research and development, are amortized on a straight‑line basis over their estimated useful lives, which range from three to ten years.

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Goodwill consists of the excess of cost over the fair value of net assets acquired in business combinations. Goodwill is not amortized but instead is tested annually for impairment on October 1, or more frequently if events occur or circumstances change that would more likely than not reduce its fair value below its carrying amount. We allocate goodwill to reporting units on a relative fair value basis.

In testing for goodwill impairment, we may first qualitatively assess whether it is more likely than not (a likelihood of more than 50 percent) that a goodwill impairment exists. If it is determined that a quantitative assessment is required, we will recognize goodwill impairment as the difference between the carrying amount of the reporting unit and it’s fair value, but not to exceed the carrying amount of goodwill within the reporting unit. There was no impairment of goodwill as a result of our annual impairment assessments conducted for the years ended December 31, 2022, 2021, and 2020.

Income taxes. We account for income taxes under the asset and liability method, which requires the recognition of deferred tax assets and liabilities for the expected future tax consequences of events that have been included in the consolidated financial statements. Under this method, deferred tax assets and liabilities are determined based on net operating loss carryforwards, credit carryforwards, and temporary differences between the financial statement and tax basis of assets and liabilities using enacted tax rates in effect for the year in which the items are expected to reverse. The effect of a change in tax rates on deferred tax assets and liabilities is recognized in income in the period of the enactment date.

We perform a quarterly assessment of the recoverability of the net deferred tax assets. We consider all available evidence, both positive and negative, in determining whether all or a portion of a deferred tax asset is more likely than not to be realized. In the event we determine that all or a portion of the deferred tax assets is not more likely than not to be realized, an adjustment to the valuation allowance would be recorded that would increase the provision for income taxes. To the extent that the realization of a deferred tax asset is based upon forecasted future earnings, our judgment regarding future profitability may change due to future market conditions and other factors. Assumptions about future taxable income require significant judgment and, while these assumptions rely heavily on estimates, such estimates are consistent with the plans we are using to manage the underlying business. Any change in future profitability may require material adjustments to these net deferred tax assets, resulting in a reduction in net income in the period when such determination is made. Additionally, future changes in tax laws and rates, including administrative or regulatory guidance, could affect recorded deferred tax assets and liabilities. Any adjustments to these estimates will generally be recorded as an income tax expense or benefit in the period the adjustment is determined.

We are subject to income taxes in the U.S. and in numerous foreign jurisdictions. The calculation of our tax liabilities often involves dealing with uncertainties in the application of complex tax laws and regulations in a multitude of jurisdictions across our global operations. There are many transactions and calculations about which the ultimate tax outcome is uncertain. A benefit from an uncertain tax position may be recognized when it is more likely than not that the position will be sustained based upon the technical merits of the position. This may include expected resolutions upon examination, any related appeals, or through a litigation processes. As a result, our calculations involve estimates by management. Due to the complexity of some of these uncertainties, the ultimate resolution may result in a payment, potentially including interest and penalties, that is materially different from our current estimates of the unrecognized tax benefit liabilities. These differences, along with any related interest and penalties, will generally be reflected as increases or decreases to income tax expense in the period in which new information becomes available. We review the tax reserves as circumstances warrant and adjust the reserves as events occur that affect our potential liability for additional taxes. We follow the applicable guidance on derecognition, classification, interest and penalties, accounting in interim periods, disclosure, and transition with respect to uncertain tax positions. We recognize interest and penalties related to income taxes within the (Provision) benefit for income taxes line in the consolidated statements of operations. Accrued interest and penalties are included within the related tax liability line in the consolidated balance sheets.

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Fair value of common stock prior to IPO. We were a privately held company with no active public market of our common stock prior to our IPO. Therefore, the estimated fair value of the common stock underlying our stock‑based awards granted prior to our IPO was determined by our board of directors, with input from management and contemporaneous third‑party valuations. We believe that our board of directors had the relevant experience and expertise to determine the fair value of our common stock prior to our IPO.

Prior to the IPO, and given the absence of a public trading market for our common stock, and in accordance with the American Institute of Certified Public Accountants practice guide, Valuation of Privately-Held-Company Equity Securities Issued as Compensation, our board of directors exercised reasonable judgment and considered numerous objective and subjective factors to determine the best estimate of the fair value of our common stock, including:

•contemporaneous independent valuations performed by an unrelated third-party valuation specialist;

•the nature of our business and its history;

•our operating and financial performance and forecast;

•present value of estimated future cash flows;

•the likelihood of achieving a liquidity event, such as an initial public offering, listing, or sale of our Company, given prevailing market condition and the nature and history of our business;

•any adjustment necessary to recognize a lack of marketability for our common stock;

•the market performance of comparable publicly traded companies; and

•the U.S. and global capital market conditions.

In valuing our common stock, our board of directors determined the equity value of our business generally using the income approach and the market comparable approach valuation methods.

The income approach estimates value based on the expectation of future cash flows that a company will generate such as cash earnings, cost savings, tax deductions, and proceeds from disposition. These future cash flows are discounted to their present values using a discount rate derived from an analysis of the cost of capital of comparable publicly traded companies in our industry or similar lines of business as of each valuation date and is adjusted to reflect the risks inherent in our cash flows.

The market comparable approach estimates value based on a comparison of the Company to comparable public companies in a similar line of business. To determine our peer group of companies, we considered public enterprises with similar operations and selected those that are similar to our size, stage of life cycle, and financial leverage. From the comparable companies, a representative market value multiple is determined and applied to our results of operations to estimate the value of the Company.

Application of these approaches involved the use of estimates, judgments, and assumptions that are highly complex and subjective, such as those regarding our expected future cash flows, cost savings and expenses, discount rates, market multiples, the selection of comparable companies, and the probability of possible future events.

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Off-Balance Sheet Arrangements:

We do not have any off‑balance sheet arrangements, as defined by applicable SEC regulations.

Recent Accounting Pronouncements:

For information regarding recent accounting guidance and the impact of this guidance on our consolidated financial statements, see Note 2 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K.

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FY 2021 10-K MD&A

SEC filing source: 0001628280-22-004474.

Extracted structurally from real Item 7 body heading to real Item 7A/8 boundary. Confidence: high. Filing date: 2022-03-01. Report date: 2021-12-31.

Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations

The following discussion should be read in conjunction with our audited consolidated financial statements and notes thereto appearing in Part II, Item 8 of this Annual Report on Form 10‑K. In addition to historical information, this discussion contains forward‑looking statements that involve risks, uncertainties, and assumptions that could cause actual results to differ materially from management’s expectations. Factors that could cause such differences are set forth in Part I, Item 1A. Risk Factors of this Annual Report on Form 10‑K.

All amounts presented in this Management’s Discussion and Analysis of Financial Condition and Results of Operations, except share and per share amounts, are presented in thousands. Additionally, many of the amounts and percentages have been rounded for convenience of presentation.

Overview:

We are a leading global provider of software for infrastructure engineering, enabling the work of civil, structural, geoprofessional, and plant engineering practitioners, their project delivery enterprises, and owner‑operators of infrastructure assets. We were founded in 1984 by the Bentley brothers and on September 25, 2020, we completed our IPO.

Our enduring commitment is to develop and support the most comprehensive portfolio of integrated software offerings across professional disciplines, project and asset lifecycles, infrastructure sectors, and geographies. Our software enables digital workflows across engineering disciplines, distributed project teams, from offices to the field, and across computing form factors, including desktops, on‑premises servers, cloud‑native services, mobile devices, and web browsers. We deliver our solutions via on‑premise, cloud, and hybrid environments. Our users engineer, construct, and operate projects and assets across the following infrastructure sectors:

•public works (including roads, rail, airports, ports, and water and wastewater networks)/utilities (including electric, gas, water, and communications). We estimate that this sector represents 52% of the net infrastructure asset value of the global top 500 infrastructure owners based on the 2021 edition of the Bentley Infrastructure 500 Top Owners, our annual compilation of the world’s largest infrastructure owners ranked by net depreciated value of their tangible fixed assets;

•industrial (including discrete and process manufacturing, power generation, and water treatment plants)/resources (including oil and gas, mining, and offshore). We estimate that this sector represents 34% of the global top 500 infrastructure owners’ net infrastructure asset value; and

•commercial/facilities (including office buildings, hospitals, and campuses). We estimate that this sector represents 14% of the global top 500 infrastructure owners’ net infrastructure asset value.

We offer solutions for enterprises and professionals across the infrastructure lifecycle. Our Engineering Applications and Geoprofessional Applications support the breadth of engineering and geoprofessional disciplines and are primarily desktop applications for professional practitioners. Our project delivery and asset performance Enterprise systems are provided via cloud and hybrid environments, developed respectively to extend enterprise collaboration during project delivery, and to manage and leverage engineering information during operations and maintenance. Our Industry Solutions solve domain‑specific problems for owners of infrastructure assets, and the project delivery ecosystems that support these owners. Our cloud-native iTwin Platform solutions enable digital twin workflows, which can span project and asset lifecycles.

We continue to make substantial investments in research and development because we believe the infrastructure engineering software market presents compelling opportunities for the application of new technologies that advance our current solutions. Our research and development roadmap balances technology advances and new offerings with continuous enhancements to existing offerings. Our allocation of research and development resources is guided by management‑established priorities, input from product managers, and user and sales force feedback.

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We bring our offerings to market primarily through direct sales channels that generated approximately 92% of our 2021 total revenues.

Since its founding, Bentley Systems has remained focused on our mission to provide software in support of the professional needs of those responsible for creating and managing the world’s infrastructure. We have methodically grown through periods of global expansion, periods of expansion in our portfolio of solutions, and periods of rapid technological change. The following provides key corporate milestones over our 37‑year history:

Our sources of revenue growth, in order of magnitude and excluding the impact from acquisitions, come from the recurrence of existing subscriptions revenues, additional revenue and growth from existing accounts using the same products, additional revenue and growth from existing accounts using new products, and growth from new accounts. For the year ended December 31, 2021, subscriptions represented 84% of our total revenues, and together with certain services revenues that are recurring in nature and represented 2% of our total revenues, bring the proportion of our recurring revenues to 86% of our total revenues. The remaining 14% of our revenues were generated from the sale of perpetual licenses and the delivery of non‑recurring services. We have a highly‑diversified account base, with our largest account representing no more than 2.5% of our total revenues in 2021. Our 2021 total revenues were also diversified by account type, size, and geography. Additionally, we believe that we have a loyal account base, with over 70% of our 2021 total revenues from organizations that have been our accounts for over ten years. Between 2001 and 2021, our total revenues had an approximately 8% compound annual growth rate.

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Our Commercial Offerings:

Our solutions are made available to our accounts in a broad range of commercial offerings designed to accommodate the diverse preferences of our accounts, which range from owned versus subscribed, short‑term subscriptions versus longer term annual subscriptions, and fee‑certain arrangements versus variable or consumption‑based arrangements with consumption measurement durations of less than one year. We contract our commercial offerings under a single form of standard contract, which includes liability and other risk protections in our favor, and appropriate standard addendums to the primary contract, which specifically address the commercial offerings provided. Our standard commercial offerings are summarized in the table below, with further descriptions following the table:

SELECT Subscriptions. Our SELECT subscription is a prepaid annual recurring subscription that accompanies a new or previously purchased perpetual license. We believe that the SELECT benefits summarized below support our favorable rates of account retention and growth:

•Software upgrades;

•Comprehensive technical support;

•License pooling providing accounts with efficiency advantages;

•Portfolio balancing providing accounts the opportunity to exchange unused or under used licenses with other of our license offerings;

•Learning benefits, Azure‑based cloud collaboration services, and mobility advantages; and

•Access to our entire application portfolio with usage of licenses not previously purchased monetized quarterly in arrears based on consumption. See the section titled “—Term License Subscriptions” below.

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Enterprise Subscriptions. Our Enterprise subscription offerings provide our largest accounts with complete and unlimited global access to our comprehensive portfolio of solutions.

•Enterprise License Subscriptions (“ELS”). Our ELS offering provides access to our comprehensive portfolio of solutions for a fixed annual fee. Subsequent annual renewals are based on the account’s usage of software in the preceding year, effectively resulting in an annual consumption‑based arrangement. The majority of our ELS subscribers were historically SELECT subscribers that have grown into a position to take full advantage of our ELS offering.

•Enterprise 365 (“E365”) Subscriptions. Under our E365 subscription, participating accounts have unrestricted access to our comprehensive software portfolio, similar to ELS, however they are charged based upon daily usage. E365 subscriptions can contain quarterly usage floors or collars as accounts transition to the usage model or for accounts within the public sector. The daily usage fee also includes a term license component, SELECT maintenance and support, hosting, and Success Blueprints, which are designed to achieve business outcomes through more efficient and effective use of our software. The E365 subscription offering was introduced during the fourth quarter of 2018. We are prioritizing efforts to transition ELS subscribers to E365 subscriptions, primarily to simplify pricing, more closely align consumption to monetization, and to establish Success Blueprints as recurring to ensure better business outcomes for our users. To the extent we succeed in transitioning subscribers to E365, we recognize a greater proportion of our revenues on a quarterly basis rather than substantially upfront. See the section titled “—Key Factors Impacting Comparability and Performance.”

Term License Subscriptions

Annual Term Licenses (“ATL”) Subscription. Annual term licenses are generally prepaid annually for named user access to specific products and include our Virtuoso subscriptions sold via our Virtuosity eStore for practitioner licenses. Virtuoso subscriptions are bundles with customizable training and expert consultation administered through “keys” or credits. ATL are also used to monetize site or enterprise wide access for certain of our AssetWise solutions within given usage bands.

Quarterly Term License (“QTL”) Subscription. Through quarterly term licenses, accounts pay quarterly in arrears for licenses they have used representing usage beyond their contracted quantities. Much like our Enterprise subscription programs, a QTL allows smaller- and medium‑sized accounts to match usage to ongoing project requirements.

Monthly Term License (“MTL”) Subscription. Monthly term licenses are identical to QTL subscriptions, except for the term of the license, and the manner in which they are monetized. MTL subscriptions require a Cloud Services Subscription, which is discussed below.

Visas and Passports. Visas and Passports are quarterly or annual term licenses enabling users to access specific project or enterprise information and entitles our users to certain functionality of our ProjectWise and AssetWise systems. Generally, a Passport provides desktop, web, and mobile application access to project information and certain functions, and a Visa provides similar access, plus added functionality depending upon the product to which the Visa is aligned.

While certain legacy arrangements are supported, our standard offering requires Visas and Passports to be fulfilled and contracted via a CSS, which is discussed below.

Cloud Services Subscription (“CSS”). CSS is designed to streamline the procurement, administration, and payment process for us and our accounts. A CSS requires an upfront annual estimation of MTL, Visa and Passport consumption, and any Success Services expected for the upcoming year. A deposit for the annual estimated consumption is submitted in advance. Actual consumption is monitored and invoiced against the deposit on a calendar quarter basis. Accounts are charged only for what gets used and deposited amounts never expire.

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Perpetual Licenses

We historically have sold perpetual licenses and continue to offer them to our accounts as an available option for most of our applications. Perpetual licenses are available for accounts that prefer to own their software licenses and may be sold with or without attaching a SELECT subscription. Historically, attachment and retention of the SELECT subscription has been high given the benefits of the SELECT subscription.

Services

We provide professional services, including training, implementation, configuration, customization, and strategic consulting services. We perform projects on both a time and materials and a fixed fee basis. Certain of our fixed‑fee arrangements, including our Success Services offerings, are structured as subscription‑like, packaged offerings that are annually recurring in nature. Success Services are standard service offerings that provide a level of dedicated professional services above the standard technical support offered to all accounts as part of their SELECT or Enterprise agreement.

Key Business Metrics:

We regularly review the following key metrics to evaluate our business, measure our performance, identify trends in our business, prepare financial projections, and make strategic decisions.

Year Ended December 31,
202120202019
Last twelve-months recurring revenues$834,150$696,662$631,097
Constant Currency:
Annualized recurring revenues (“ARR”) growth rate26%8%12%
Account retention rate98%98%98%(1)
Recurring revenues dollar-based net retention rate109%107%108%(1)

(1)On January 1, 2019, we adopted FASB ASU No. 2014‑09, Revenue from Contracts with Customers, and related amendments (“Topic 606”), which superseded the guidance provided by Accounting Standards Codification (“ASC”) 985‑605, Software-Revenue Recognition, and Topic 605‑25, Revenue Recognition, Multiple-Element Arrangements. We refer to ASC 985‑605 and Topic 605‑25 collectively as “Topic 605.” Prior to the year ended December 31, 2020, the account retention rate and recurring revenues dollar‑based net retention rate were calculated using revenues recognized pursuant to Topic 605 for all periods in order to enhance comparability during our transition to Topic 606 as we did not have all information that was necessary to calculate account retention rate pursuant to Topic 606 for earlier periods.

Last twelve‑months recurring revenues. Last twelve‑months recurring revenues is calculated as recurring revenues recognized over the preceding twelve‑month period. We define recurring revenues as subscriptions revenues that recur monthly, quarterly, or annually with specific or automatic renewal clauses and services revenues in which the underlying contract is based on a fixed fee and contains automatic annual renewal provisions.

We believe that last twelve‑months recurring revenues is an important indicator of our performance during the immediately preceding twelve‑month time period. We believe that we will continue to experience favorable growth in recurring revenues primarily due to our strong account retention and recurring revenues dollar‑based net retention rates, as well as the addition of new accounts with recurring revenues. The last twelve‑months recurring revenues for the periods ended December 31, 2021, 2020, and 2019 compared to the last twelve‑months of the preceding twelve‑month period increased by $137,488, $65,565, and $44,631, respectively. This increase was primarily due to growth in ARR, which is primarily the result of growth in our recurring revenues dollar‑based net retention rate, as well as additional recurring revenues resulting from new accounts and acquisitions. For the twelve months ended December 31, 2021, 2020, and 2019, 86%, 87%, and 86%, respectively, of our revenues were recurring revenues.

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Constant currency metrics. In reporting period‑over‑period results, we calculate the effects of foreign currency fluctuations and constant currency information by translating current period results using prior period average foreign currency exchange rates. Our definition of constant currency may differ from other companies reporting similarly named measures, and these constant currency performance measures should be viewed in addition to, and not as a substitute for, our operating performance measures calculated in accordance with accounting principles generally accepted in the United States of America (“U.S. GAAP”).

ARR growth rate. Our ARR growth rate is the growth rate of our ARR, measured on a constant currency basis. Our ARR is defined as the sum of the annualized value of our portfolio of contracts that produce recurring revenues as of the last day of the reporting period, and the annualized value of the last three months of recognized revenues for our contractually recurring consumption‑based software subscriptions with consumption measurement durations of less than one year. We believe that the last three months of recognized revenues, on an annualized basis, for our recurring software subscriptions with consumption measurement period durations of less than one year is a reasonable estimate of the annual revenues, given our consistently high retention rate and stability of usage under such subscriptions. ARR resulting from the annualization of recurring contracts with consumption measurement durations of less than one year, as a percentage of total ARR, was 38%, 36%, and 25% as of December 31, 2021, 2020, and 2019, respectively. Within our consumption‑measured ARR, the continuous uptake of our E365 subscription offering has introduced daily consumption‑measured ARR, representing 29% of total ARR as of December 31, 2021. ARR is inclusive of the ARR of acquired companies as of the date they are acquired. We believe that ARR and ARR growth are important metrics indicating the scale and growth of our business. Furthermore, we believe ARR, considered in connection with our recurring revenues dollar‑based net retention rate, is a leading indicator of revenue growth. Our ARR as of December 31, 2021 was $921,218, calculated using the spot foreign exchange rates as of December 31, 2021.

For the year ended December 31, 2021, our ARR growth rate was favorably impacted from the Seequent acquisition by 13%.

Account retention rate. Our account retention rate for any given twelve-month period is calculated using the average currency exchange rates for the prior period, as follows: the prior period recurring revenues from all accounts with recurring revenues in the current and prior period, divided by total recurring revenues from all accounts during the prior period. The account retention rate for the years ended December 31, 2021 and 2020 was calculated under Topic 606. For the year ended December 31, 2019, the account retention rate was calculated using revenues recognized pursuant to Topic 605 as we did not have all information that was necessary to calculate account retention rate pursuant to Topic 606. Our account retention rate is an important indicator that provides insight into the long‑term value of our account relationships and our ability to retain our account base. We believe that our consistent and high account retention rates illustrate our ability to retain and cultivate long‑term relationships with our accounts.

Recurring revenues dollar‑based net retention rate. Our recurring revenues dollar‑based net retention rate is calculated using the average exchange rates for the prior period, as follows: the recurring revenues for the current period, including any growth or reductions from existing accounts, but excluding recurring revenues from any new accounts added during the current period, divided by the total recurring revenues from all accounts during the prior period. A period is defined as any trailing twelve months. The recurring revenues dollar‑based net retention rate for the years ended December 31, 2021 and 2020 was calculated under Topic 606. For the year ended December 31, 2019, the recurring revenues dollar‑based net retention rate was calculated using revenues recognized pursuant to Topic 605 as we did not have all information that was necessary to calculate recurring revenues dollar‑based net retention rate pursuant to Topic 606. We believe our recurring revenues dollar‑based net retention rate is a key indicator of our success in growing our revenues within our existing accounts. Given that recurring revenues represented 86% of our total revenues for the twelve months ended December 31, 2021, this metric helps explain our revenue performance as primarily growth into existing accounts. We believe that our consistent and high recurring revenues dollar‑based net retention rate illustrates our ability to consistently retain accounts and grow them.

Our calculation of these metrics may not be comparable to other companies with similarly‑titled metrics.

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Non-GAAP Financial Measures:

In addition to our results determined in accordance with U.S. GAAP, we also use the below non‑GAAP financial information to evaluate our ongoing operations and for internal planning and forecasting purposes.

Year Ended December 31,
202120202019
Adjusted EBITDA$324,948$266,376$188,537
Adjusted Net Income266,940192,812135,357

Adjusted EBITDA. We define Adjusted EBITDA as net income adjusted for interest expense, net, provision (benefit) for income taxes, depreciation and amortization, stock‑based compensation, expense (income) relating to deferred compensation plan liabilities, acquisition expenses, realignment expenses, expenses associated with IPO, other non‑operating (income) expense, net, and (income) loss from investment accounted for using the equity method, net of tax.

Adjusted Net Income. We define Adjusted Net Income as net income adjusted for the following: amortization of purchased intangibles and developed technologies, stock‑based compensation, expense (income) relating to deferred compensation plan liabilities, acquisition expenses, realignment expenses, expenses associated with IPO, other non‑operating (income) expense, net, the tax effect of the above adjustments to net income, and (income) loss from investment accounted for using the equity method, net of tax. The tax effect of adjustments to net income is based on the estimated marginal effective tax rates in the jurisdictions impacted by such adjustments.

Adjusted EBITDA and Adjusted Net Income are not presentations made in accordance with U.S. GAAP, and our use of the terms Adjusted EBITDA and Adjusted Net Income may vary from the use of similarly titled measures by others in our industry due to the potential inconsistencies in the method of calculation and differences due to items subject to interpretation. We believe the presentation of Adjusted EBITDA and Adjusted Net Income provides useful information to management and investors regarding financial and business trends related to our results of operations and that when non‑GAAP financial information is viewed with U.S. GAAP financial information, investors are provided with a more meaningful understanding of our ongoing operating performance. We also use Adjusted EBITDA and Adjusted Net Income to compare our results to those of our competitors and to consistently measure our performance from period to period. During the third quarter of 2021, we modified our definitions of Adjusted EBITDA and Adjusted Net Income to adjust for expense (income) relating to deferred compensation plan liabilities and amounts for all periods herein reflect application of the modified definition.

Adjusted EBITDA and Adjusted Net Income should not be considered as alternatives to net income, operating income, or any other performance measures derived in accordance with U.S. GAAP as measures of operating performance. Adjusted EBITDA and Adjusted Net Income have important limitations as analytical tools and should not be considered in isolation or as a substitute for analysis of our results as reported under U.S. GAAP.

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Reconciliation of net income to Adjusted EBITDA:

Year Ended December 31,
202120202019
Net income$93,192$126,521$103,096
Interest expense, net12,4917,4768,199
(Benefit) provision for income taxes(3,448)38,62523,738
Depreciation and amortization (1)52,79336,11732,160
Stock-based compensation (3)48,15232,1148,091
Deferred compensation plan (4)95,046177408
Acquisition expenses (5)34,36811,6666,597
Realignment expenses (6)10,022(584)
Expenses associated with IPO (7)26,130
Other (income) expense, net (8)(11,231)(24,946)5,557
Loss from investment accounted for using the equity method, net of tax3,5852,4741,275
Adjusted EBITDA$324,948$266,376$188,537

Reconciliation of net income to Adjusted Net Income:

Year Ended December 31,
202120202019
Net income$93,192$126,521$103,096
Non-GAAP adjustments, prior to income taxes:
Amortization of purchased intangibles and developed technologies (2)34,00120,72118,731
Stock-based compensation (3)48,15232,1148,091
Deferred compensation plan (4)95,046177408
Acquisition expenses (5)34,36811,6666,597
Realignment expenses (6)10,022(584)
Expenses associated with IPO (7)26,130
Other (income) expense, net (8)(11,231)(24,946)5,557
Total non-GAAP adjustments, prior to income taxes200,33675,88438,800
Income tax effect of non-GAAP adjustments(30,173)(12,067)(7,814)
Loss from investment accounted for using the equity method, net of tax3,5852,4741,275
Adjusted Net Income$266,940$192,812$135,357

Further explanation of certain of our adjustments in arriving at Adjusted EBITDA and Adjusted Net Income are as follows:

(1)Depreciation and amortization. Depreciation and amortization includes amortization of $7,020, $4,699, and $3,516 for the years ended December 31, 2021, 2020, and 2019, respectively, related to certain projects under our Accelerated Commercial Development Program (“ACDP”).

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(2)Amortization of purchased intangibles and developed technologies. Amortization of purchased intangibles varies in amount and frequency and is significantly impacted by the timing and size of our acquisitions. Amortization of acquisition related developed technologies under our ACDP was $275, $388, and $723 for the years ended December 31, 2021, 2020, and 2019, respectively. Management finds it useful to exclude these non‑cash charges from our operating expenses to assist in budgeting, planning, and forecasting future periods. The use of intangible assets and developed technologies contributed to our revenues earned during the periods presented and will also contribute to our revenues in future periods. Amortization of purchased intangible assets and developed technologies will recur in future periods.

(3)Stock‑based compensation. We exclude certain stock‑based compensation expenses from our non‑GAAP measures primarily because they are non‑cash expenses and management finds it useful to exclude certain non‑cash charges to assess the appropriate level of various operating expenses to assist in budgeting, planning, and forecasting future periods. Moreover, because of varying available valuation methodologies, subjective assumptions and the variety of award types that companies can use under FASB ASC Topic 718, Compensation—Stock Compensation, we believe excluding stock‑based compensation expenses allows investors to make meaningful comparisons between our recurring core business results of operations and those of other companies.

(4)Deferred compensation plan. In August 2021, our board of directors approved an amendment to the Company’s unfunded Nonqualified Deferred Compensation Plan, as amended and restated, effective as of September 22, 2020 (the “DCP”), which offered to certain active executives in the DCP a one‑time, short‑term election to reallocate a limited portion of their DCP holdings from phantom shares of the Company’s Class B Common Stock into other DCP phantom investment funds. The offer to reallocate was subject to a proration mechanism which adjusted the aggregate elections to a maximum of 1,500,000 phantom shares of the Company’s Class B Common Stock. This one‑time reallocation opportunity was offered only to certain active executives (but not to Directors or Bentley family members) in order to encourage retention, as otherwise these executives could only have materially diversified their investments in Company equity (primarily held in the DCP) by voluntarily terminating employment to trigger DCP distributions. These executives in aggregate accordingly diversified 24% of their phantom shares of the Company’s Class B Common Stock. While DCP participants’ investments in phantom shares remain equity classified, as they will be settled in shares of Class B Common Stock upon eventual distribution, the amendment and elections resulted in a change to liability classification for the reallocated phantom investments, as they will be settled in cash upon eventual distribution. As a result, during the year ended December 31, 2021, we recognized a one‑time compensation charge of $90,721 to Deferred compensation plan expenses in the consolidated statements of operations to record the reallocated deferred compensation plan liabilities at their fair value. Deferred compensation plan liabilities are marked to market at the end of each reporting period, with changes in the liabilities recorded as an expense (income) to Deferred compensation plan in the consolidated statements of operations. We exclude these charges because they are not reflective of our ongoing business and results of operation. We believe it is useful for investors to understand the effects of these items on our total operating expenses.

(5)Acquisition expenses. We incur expenses for professional services rendered in connection with business combinations, which are included in our U.S. GAAP presentation of general and administrative expense. Also included in our acquisition expenses are retention incentives paid to executives of the acquired companies, as well as adjustments related to deferred revenues from acquisitions that closed prior to 2021. The adjustment to acquired deferred revenues has no impact on our business or cash flow, but it does reduce reported U.S. GAAP revenues in the periods following an acquisition. We exclude these acquisition expenses when we evaluate our continuing operational performance as we would not have otherwise incurred these expenses in the periods presented as part of our continuing operations. For the year ended December 31, 2021, $16,557 of our acquisition expenses related to the acquisition of Seequent.

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(6)Realignment expenses. These expenses are associated with realigning our business strategies to better serve our accounts and to better align resources with the evolving needs of the business. In connection with these actions, we recognize costs related to termination benefits for colleagues whose positions were eliminated. We exclude these charges because they are not reflective of our ongoing business and results of operations. We believe it is useful for investors to understand the effects of these items on our total operating expenses. In the ordinary course of operating our business, we incur severance expenses that are not included in this adjustment.

(7)Expenses associated with IPO. These expenses include certain non-recurring costs relating to our IPO, consisting of the payment of underwriting discounts and commissions applicable to the sale of shares by the selling stockholders, professional fees, and other expenses. We exclude these charges because they are not reflective of our ongoing business and results of operation. We believe it is useful for investors to understand the effects of these items on our total operating expenses.

(8)Other (income) expense, net. Primarily consists of foreign exchange (gains) losses of $(827), $(22,919), and $5,591 for the years ended December 31, 2021, 2020, and 2019, respectively. The foreign exchange (gains) losses derive primarily from U.S. Dollar denominated cash and cash equivalents, accounts receivable, and intercompany balances held by foreign subsidiaries. The gains and losses from such translations are included in Other (income) expense, net in the consolidated statements of operations. Intercompany finance transactions denominated in U.S. Dollars resulted in unrealized foreign exchange losses (gains) of $779, $(22,310), and $5,270 for the years ended December 31, 2021, 2020, and 2019, respectively. These U.S. Dollar denominated balances are being translated into their functional currencies at the rates in effect at the balance sheet date and are fully eliminated in consolidation. For the year ended December 31, 2021, other (income) expense, net includes a gain from the change in fair value of our interest rate swap of $9,770. For the year ended December 31, 2020, other (income) expense, net includes a gain from the change in fair value of our interest rate swap of $347 and a gain from the change in fair value of acquisition contingent consideration of $1,340. We exclude these charges because they are not reflective of ongoing business and results of operations. We believe it is useful for investors to understand the effects of these items on our total operating expenses.

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Key Factors Impacting Comparability and Performance:

Highlights for the year ended December 31, 2021. In addition to our performance previously discussed in “—Key Business Metrics” and “—Non-GAAP Financial Measures,” and as discussed further below in “—Results of Operations” and “—Liquidity and Capital Resources,” our consolidated financial statements for the year ended December 31, 2021 were impacted by the following:

•On June 17, 2021, we completed the acquisition of Seequent, a leader in software for geological and geophysical modeling, geotechnical stability, and cloud services for geodata management and collaboration, for approximately $883,336 in cash, net of cash acquired, plus 3,141,342 shares of our Class B Common Stock. For the year ended December 31, 2021, we incurred $16,557 of expenses related to the acquisition of Seequent;

•On June 28, 2021, we completed a private offering of $575,000 of 0.375% convertible senior notes due 2027. We incurred $15,065 of expenses in connection with the 2027 Notes offering consisting of the payment of initial purchasers’ discounts and commissions, professional fees, and other expenses (“transaction costs”). Transaction costs were recorded as a direct deduction from the related debt liability in the consolidated balance sheet and are amortized to interest expense over the term of the 2027 Notes;

•In connection with the pricing of the 2027 Notes, we entered into capped call options with certain of the initial purchasers or their respective affiliates and certain other financial institutions. The capped call options are expected to reduce potential dilution to our Class B Common Stock upon any conversion of 2027 Notes and/or offset any cash payments we are required to make in excess of the principal amount of converted notes, as the case may be, with such reduction and/or offset subject to a cap. We paid premiums of $25,875 in connection with the capped call options. The capped call options are indexed to our common stock and classified in stockholders’ equity. As such, the premiums paid for the capped call options have been included as a net reduction to Additional paid-in capital in the consolidated balance sheet;

•On January 26, 2021, we completed a private offering of $690,000 of 0.125% convertible senior notes due 2026. We incurred $18,055 of expenses in connection with the 2026 Notes offering consisting of transaction costs. Transaction costs were recorded as a direct deduction from the related debt liability in the consolidated balance sheet and are amortized to interest expense over the term of the 2026 Notes;

•In connection with the pricing of the 2026 Notes, we entered into capped call options with certain of the initial purchasers or their respective affiliates and certain other financial institutions. The capped call options are expected to reduce potential dilution to our Class B Common Stock upon any conversion of 2026 Notes and/or offset any cash payments we are required to make in excess of the principal amount of converted notes, as the case may be, with such reduction and/or offset subject to a cap. We paid premiums of $25,530 in connection with the capped call options. The capped call options are indexed to our common stock and classified in stockholders’ equity. As such, the premiums paid for the capped call options have been included as a net reduction to Additional paid-in capital in the consolidated balance sheet;

•On January 25, 2021, we entered into the Second Amendment to the Credit Facility, which increased the senior secured revolving loan facility from $500,000 to $850,000 and extended the maturity date from December 18, 2022 to November 15, 2025. We performed an extinguishment versus modification assessment on a lender‑by‑lender basis resulting in the write‑off of unamortized debt issuance costs of $353 and the capitalization of fees paid to lenders and third parties of $3,577. Debt issuance costs are amortized to interest expense through the maturity date of November 15, 2025;

•On December 22, 2021, we entered into the Fourth Amendment to the Credit Facility, which provided for a new $200,000 senior secured term loan with a maturity of November 15, 2025 (the “2021 Term Loan”). We incurred $540 of debt issuance costs related to the 2021 Term Loan. We used borrowings under the 2021 Term Loan to pay down borrowings under the swingline sub‑facility and revolving facility under the Credit Facility;

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•In August 2021, our board of directors approved an amendment to the DCP, which offered to certain active executives in the DCP a one‑time, short‑term election to reallocate a limited portion of their DCP holdings from phantom shares of our Class B Common Stock into other DCP phantom investment funds. The offer to reallocate was subject to a proration mechanism which adjusted the aggregate elections to a maximum of 1,500,000 phantom shares of the Company’s Class B Common Stock. This one‑time reallocation opportunity was offered only to certain active executives (but not to Directors or Bentley family members) in order to encourage retention, as otherwise these executives could only have materially diversified their investments in Company equity (primarily held in the DCP) by voluntarily terminating employment to trigger DCP distributions. These executives in aggregate accordingly diversified 24% of their phantom shares of the Company’s Class B Common Stock. While DCP participants’ investments in phantom shares remain equity classified, as they will be settled in shares of Class B Common Stock upon eventual distribution, the amendment and elections resulted in a change to liability classification for the reallocated phantom investments, as they will be settled in cash upon eventual distribution. As a result, during the year ended December 31, 2021, we recognized a one‑time compensation charge of $90,721 to Deferred compensation plan expenses in the consolidated statements of operations to record the reallocated deferred compensation plan liabilities at their fair value. Subsequent to the one‑time reallocation, these diversified deferred compensation plan liabilities are marked to market at the end of each reporting period, with changes in the liabilities recorded as an expense (income) to Deferred compensation plan in the consolidated statements of operations;

•Effective as of the beginning of the fourth quarter of 2020, participants in the Bentley Systems, Incorporated Bonus Pool Plan, as amended and restated, effective as of September 22, 2020 (the “Bonus Plan”) may elect to receive any portion, or all, of such participants’ non‑deferred incentive bonus in the form of shares of fully vested Class B Common Stock instead of cash payments and subject to a combined quarterly limit of $7,500. For the year ended December 31, 2021, we recorded $23,121 of stock‑based compensation expense related to this plan, as compared to $6,524 during the fourth quarter of 2020; and

•Effective September 22, 2020, our board of directors and stockholders adopted and approved the Bentley Systems, Incorporated Global Employee Stock Purchase Plan (the “ESPP”). The ESPP has been implemented by means of consecutive offering periods, with the first offering period commencing on the first trading day on or after January 1, 2021 and ending on the last trading day on or before June 30, 2021. For the year ended December 31, 2021, we recorded $2,118 of stock‑based compensation expense related to this plan.

Impact of foreign currency. A portion of our total revenues and operating expenses were derived from outside the U.S. and as such, were denominated in various foreign currencies, including most significantly: Euros, British Pounds, Australian Dollars, Canadian Dollars, Chinese Yuan Renminbi, and New Zealand Dollars. Our financial results are therefore affected by changes in foreign currency rates. In 2021, 47% of our total revenues were denominated in various foreign currencies. Correspondingly, in 2021, 42% of our total operating expenses were denominated in various foreign currencies. Other than the natural hedge attributable to matching revenues and expenses in the same currencies, we do not currently hedge foreign currency exposure. Accordingly, our results of operations have been, and in the future will be, affected by changes in foreign exchange rates.

We identify the effects of foreign currency on our operations and present constant currency growth rates and fluctuations because we believe exchange rates are an important factor in understanding period‑over‑period comparisons and enhance the understanding of our results and evaluation of our performance. In reporting period to period results, we calculate the effects of foreign currency fluctuations and constant currency information by translating current period results using prior period average foreign currency exchange rates. Our definition of constant currency may differ from other companies reporting similarly named measures, and these constant currency performance measures should be viewed in addition to, and not as a substitute for, our operating performance measures calculated in accordance with U.S. GAAP.

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Acquisitions. Historically, we have enhanced our business with acquisitions of businesses, software solutions, and technologies. Going forward, we plan to selectively acquire adjacent software solutions that can be sold broadly across our account base, as well as to acquire new technologies that we can leverage across our existing software solution portfolio. We completed 13 and six acquisitions for the years ended December 31, 2021 and 2020, respectively.

Impact of COVID‑19. In March 2020, the World Health Organization declared a global pandemic related to the rapidly growing outbreak of the disease COVID‑19, caused by a novel strain of coronavirus, SARS‑CoV‑2. In response to the COVID-19 pandemic, we implemented a number of initiatives to ensure the safety of our colleagues and enable them to move to a work from home environment seamlessly and continue working effectively. We continue to monitor the global situation, with the health and safety of our colleagues and users as a top priority. Currently, the majority of our workforce remains remote due to COVID-19.

Our business model is such that we have experienced minimal disruption to our ability to deliver our solutions to accounts. The COVID‑19 pandemic has had a modest impact on the usage of our solutions by our users. Throughout 2020 and 2021, usage rates fluctuated modestly when compared to the corresponding periods in the prior year. Usage declines have had a minimal impact on our recurring revenues, which are comprised primarily of longer term contracts where short‑term usage rate declines do not adversely impact revenues. However, to the extent declines in usage have also occurred within our recurring revenue contracts with shorter term resets, as is the case with our E365 contracts, the usage declines have modestly impacted revenues. Our services revenues have also been impacted as certain accounts have delayed new projects. Overall, while our rate of growth has been impacted, our revenues have continued to grow given the mission critical nature of our solutions.

As a precaution in the COVID-19 environment, we have and continue to actively manage our spending. Actions taken during 2020 included efforts to minimize colleague travel, and to reduce and recharacterize promotional spending with a shift to virtual events. Although compensation levels and incentive plan payouts have returned to normal for 2021, during 2020 our actions also included curtailment in variable compensation plans to align to COVID-19 pandemic related uncertainties. These actions have resulted in substantial cost savings during the pandemic, which are unlikely to be fully sustainable prospectively.

For further discussion of the potential impact of COVID-19 on our business, see Part I, Item 1A. Risk Factors of this Annual Report on Form 10-K.

Components of Results of Operations:

We manage our business globally within one operating segment, the development and marketing of computer software and related services, which is consistent with how our chief operating decision maker reviews and manages our business.

Revenues

We generate revenues from subscriptions, perpetual licenses, and services.

Subscriptions

SELECT subscriptions. We provide prepaid annual recurring subscriptions that accounts can elect to add to a new or previously purchased perpetual license. SELECT provides accounts with benefits, including upgrades, comprehensive technical support, pooled licensing benefits, annual portfolio balancing exchange rights, learning benefits, certain Azure‑based cloud collaboration services, mobility advantages, and access to other available benefits. SELECT subscriptions revenues are recognized as distinct performance obligations are satisfied.

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Enterprise subscriptions. We also provide Enterprise subscription offerings, which provide our largest accounts with complete and unlimited global access to our comprehensive portfolio of solutions. ELS provides access for a prepaid fee. Our E365 subscription, which was introduced during the fourth quarter of 2018, provides unrestricted access to our comprehensive software portfolio, similar to ELS, however is charged based upon daily usage. E365 subscriptions can contain quarterly usage floors or collars as accounts transition to the usage model or for accounts within the public sector. The daily usage fee also includes a term license component, SELECT maintenance and support, hosting, and Success Blueprints, which are designed to achieve business outcomes through more efficient and effective use of our software. The ELS and E365 offerings both contain a distinct term license component. ELS revenues are recognized as the distinct performance obligations are satisfied. E365 revenues are recognized based upon usage incurred by the account.

Term license subscriptions. We provide annual, quarterly, and monthly term licenses for our software products. ATL subscriptions are generally prepaid annually for named user access to specific products and include our Virtuoso subscriptions sold via our Virtuosity eStore for practitioner licenses. Virtuoso subscriptions are bundles with customizable training and expert consultation administered through “keys” or credits. QTL subscriptions allow accounts to pay quarterly in arrears for license usage that is beyond their SELECT contracted quantities. MTL subscriptions are identical to QTL subscriptions, except for the term of the license, and the manner in which they are monetized. MTL subscriptions require a CSS, which is described below.

Visas and Passports are quarterly or annual term licenses enabling users to access specific project or enterprise information and entitles users to certain functionality of our ProjectWise and AssetWise systems. Our standard offerings are usage based with monetization through our CSS program as described below. Annual, quarterly, and monthly term licenses revenues are recognized as the distinct performance obligations for each are satisfied. Billings in advance are recorded as Deferred revenues in the consolidated balance sheets. QTL, MTL, Visas and Passports subscriptions are recognized based upon usage incurred by the account.

CSS is a program designed to streamline the procurement, administration, and payment process. The program requires an estimation of annual usage for CSS eligible offerings and a deposit of funds in advance. Actual consumption is monitored and invoiced against the deposit on a calendar quarter basis. CSS balances not utilized for eligible products or services may roll over to future periods or are refundable. Paid and unconsumed CSS balances are recorded in Accruals and other current liabilities in the consolidated balance sheets. Software and services consumed under CSS are recognized pursuant to the applicable revenue recognition guidance for the respective software or service and classified as subscriptions or services based on their respective nature.

Perpetual licenses

Perpetual licenses may be sold with or without attaching a SELECT subscription. Historically, attachment and retention of the SELECT subscription has been high given the benefits of the SELECT subscription discussed above. Perpetual licenses revenues are recognized upon delivery of the license to the user.

Services

We provide professional services, including training, implementation, configuration, customization, and strategic consulting services. We perform projects on both a time and materials and a fixed fee basis. Certain of our fixed‑fee arrangements, including our Success Services offerings, are structured as subscription‑like, packaged offerings that are annually recurring in nature. Success Services are standard service offerings that provide a level of dedicated professional services above the standard technical support offered to all accounts as part of their SELECT or Enterprise agreement. Revenues are recognized as services are performed.

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Headcount-related costs

For the years ended December 31, 2021, 2020, and 2019, approximately 80% of our aggregate cost of revenues, and research and development, selling and marketing, and general and administrative expenses were represented by what we refer to herein as “headcount-related” costs. These costs primarily include salaries, incentives, benefits, employment taxes, travel, and realignment of our colleagues, and third‑party personnel and related overhead. Our headcount‑related costs are variable in nature. We actively manage these costs to align to our trending run rate of revenue performance, with the objective of enhancing visibility and predictability of resulting operating profit margins.

Cost of subscriptions, licenses, and services

Cost of subscriptions and licenses. Cost of subscriptions and licenses includes salaries and other related costs, including the depreciation of property and equipment and the amortization of capitalized software costs associated with servicing software subscriptions, the amortization of intangible assets associated with acquired software and technology, channel partner compensation for providing sales coverage to subscribers, as well as cloud‑related costs incurred for servicing our accounts using cloud provisioned solutions and our license administration platform.

Cost of services. Cost of services includes salaries for internal and third‑party personnel and related overhead costs, including depreciation of property and equipment and amortization of capitalized software costs, for providing training, implementation, configuration, and customization services to accounts.

Operating expenses

Research and development. Research and development expenses, which are generally expensed as incurred, primarily consist of personnel and related costs of our research and development staff, including salaries, incentives, and benefits, and costs of certain third‑party contractors, as well as allocated overhead costs. We expense software development costs, including costs to develop software products or the software component of products to be sold, leased, or marketed to external accounts, before technological feasibility is reached. In general, technological feasibility is reached shortly before the release of such products and as a result, development costs that meet the criteria for capitalization were not material for the periods presented.

Under our ACDP (our structured approach to an in‑house business incubator function), we capitalize certain development costs related to certain projects once technological feasibility is established. Technological feasibility is established when a detailed program design has been completed and documented; we have established that the necessary skills, hardware, and software technology are available to produce the product; and there are no unresolved high‑risk development issues. Once the software is ready for its intended use, amortization is recorded over the software’s estimated useful life (generally three years). Total costs capitalized under the ACDP were $6,608, $7,809, and $6,060 for the years ended December 31, 2021, 2020, and 2019, respectively. Additionally, total ACDP related amortization recorded in Costs of subscriptions and licenses was $7,020, $4,699, and $3,516 for the years ended December 31, 2021, 2020, and 2019, respectively.

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Selling and marketing. Selling and marketing expenses include salaries, benefits, bonuses, and stock‑based compensation expense for our selling and marketing colleagues, the expense of travel, entertainment, and training for such personnel, online marketing, product marketing and other brand‑building activities, such as advertising, trade shows, and expositions, various sales and promotional programs, and costs of computer equipment and facilities used in selling and marketing activities. We anticipate that we will continue to make strategic investments in our global business systems and methods to enhance major account sales activities and to support our worldwide sales and marketing strategies, and the business in general. We capitalize certain incremental costs of obtaining a contract and recognize these expenses over the period of benefit associated with these costs, resulting in a deferral of certain contract costs each period. The contract costs are amortized based on the economic life of the goods and services to which the contract costs relate. We apply a practical expedient to expense costs as incurred for costs to obtain a contract with a customer when the amortization period would have been one year or less. These costs include our internal sales force compensation program and certain channel partner sales incentive programs for which the annual compensation is commensurate with annual sales activities.

General and administrative. General and administrative expenses include salaries, bonuses, benefits, and stock‑based compensation expense for our finance, human resources, and legal colleagues, the expense of travel, entertainment, and training for such personnel, professional fees for legal and accounting services, and costs of computer equipment and facilities used in general and administrative activities. Following the completion of the IPO, we continued to incur additional expenses as a result of operating as a public company, including costs to comply with the rules and regulations applicable to companies listed on a U.S. securities exchange and costs related to compliance and reporting obligations pursuant to the rules and regulations of the SEC. In addition, as a public company, we incur increased expenses in the areas of insurance, investor relations, and professional services. As a result, we expect the dollar amount of our general and administrative expenses to increase for the foreseeable future. We expect, however, that our general and administrative expenses will decrease as a percentage of our total revenues over time, although the percentage may fluctuate from period to period depending on fluctuations in our revenue and the timing and extent of our general and administrative expenses.

Deferred compensation plan. In August 2021, our board of directors approved an amendment to the DCP, which offered to certain active executives in the DCP a one‑time, short‑term election to reallocate a limited portion of their DCP holdings from phantom shares of the Company’s Class B Common Stock into other DCP phantom investment funds. The offer to reallocate was subject to a proration mechanism which adjusted the aggregate elections to a maximum of 1,500,000 phantom shares of the Company’s Class B Common Stock. This one‑time reallocation opportunity was offered only to certain active executives (but not to Directors or Bentley family members) in order to encourage retention, as otherwise these executives could only have materially diversified their investments in Company equity (primarily held in the DCP) by voluntarily terminating employment to trigger DCP distributions. These executives in aggregate accordingly diversified 24% of their phantom shares of the Company’s Class B Common Stock. While DCP participants’ investments in phantom shares remain equity classified, as they will be settled in shares of Class B Common Stock upon eventual distribution, the amendment and elections resulted in a change to liability classification for the reallocated phantom investments, as they will be settled in cash upon eventual distribution. As a result, during the year ended December 31, 2021, we recognized a one‑time compensation charge of $90,721 to Deferred compensation plan expenses in the consolidated statements of operations to record the reallocated deferred compensation plan liabilities at their fair value. Deferred compensation plan liabilities are marked to market at the end of each reporting period, with changes in the liabilities recorded as an expense (income) to Deferred compensation plan in the consolidated statements of operations.

Amortization of purchased intangibles. Amortization of purchased intangibles includes the amortization of acquired non‑product related intangible assets, primarily customer relationships, trademarks, and non‑compete agreements recorded in connection with completed acquisitions.

Expenses associated with initial public offering. Expenses associated with IPO include certain non-recurring costs relating to our IPO, consisting of the payment of underwriting discounts and commissions applicable to the sale of shares by the selling stockholders, professional fees, and other expenses. We completed our IPO on September 25, 2020. These fees were expensed in the period incurred.

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Interest expense, net

Interest expense, net primarily represents interest associated with the Credit Facility, the 2026 Notes, and the 2027 Notes, amortization and write‑off of deferred debt issuance costs, and interest income from our investments in money market funds.

Other income (expense), net

Other income (expense), net primarily consists of foreign currency translation results derived primarily from U.S. Dollar denominated cash and cash equivalents, accounts receivable, and intercompany balances held by foreign subsidiaries with non‑U.S. Dollar functional currencies. Other income (expense), net also includes the fair value valuation result of our interest rate swap and changes in fair value of acquisition contingent consideration.

(Provision) benefit for income taxes

(Provision) benefit for income taxes includes the aggregate consolidated income tax expense for U.S. domestic and foreign income taxes.

Loss from investment accounted for using the equity method, net of tax

Loss from investment accounted for using the equity method includes our proportional share of loss in a joint venture.

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Results of Operations:

The following table sets forth selected consolidated statements of operations data for each of the periods indicated:

Year Ended December 31,
202120202019
Revenues:
Subscriptions$812,807$679,273$608,300
Perpetual licenses53,08057,38259,693
Subscriptions and licenses865,887736,655667,993
Services99,15964,88968,661
Total revenues965,046801,544736,654
Cost of revenues:
Cost of subscriptions and licenses124,32195,80371,578
Cost of services92,21871,35272,572
Total cost of revenues216,539167,155144,150
Gross profit748,507634,389592,504
Operating expenses:
Research and development220,915185,515183,552
Selling and marketing162,240143,791155,294
General and administrative150,116113,27497,172
Deferred compensation plan95,046177408
Amortization of purchased intangibles25,60115,35214,213
Expenses associated with initial public offering26,130
Total operating expenses653,918484,239450,639
Income from operations94,589150,150141,865
Interest expense, net(12,491)(7,476)(8,199)
Other income (expense), net11,23124,946(5,557)
Income before income taxes93,329167,620128,109
Benefit (provision) for income taxes3,448(38,625)(23,738)
Loss from investment accounted for using the equity method, net of tax(3,585)(2,474)(1,275)
Net income93,192126,521103,096
Less: Net income attributable to participating securities(9)(234)(8)
Net income attributable to Class A and Class B common stockholders$93,183$126,287$103,088
Per share information:
Net income per share, basic$0.30$0.44$0.36
Net income per share, diluted$0.30$0.42$0.35
Weighted average shares, basic305,711,345289,863,272284,625,642
Weighted average shares, diluted314,610,814299,371,129293,796,707

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In reporting period‑over‑period results, we calculate the effects of foreign currency fluctuations and constant currency information by translating current period results using prior period average foreign currency exchange rates. Our definition of constant currency may differ from other companies reporting similarly named measures, and these constant currency performance measures should be viewed in addition to, and not as a substitute for, our operating performance measures calculated in accordance with U.S. GAAP.

Comparison of the Years Ended December 31, 2021 and 2020

Revenues

Comparison
Year EndedConstant
December 31,Currency
20212020Amount%%
Revenues:
Subscriptions$812,807$679,273$133,53419.7%17.6%
Perpetual licenses53,08057,382(4,302)(7.5)%(8.9)%
Subscriptions and licenses865,887736,655129,23217.5%15.6%
Services99,15964,88934,27052.8%48.6%
Total revenues$965,046$801,544$163,50220.4%18.2%

Total revenues increased by $163,502, or 20.4%, to $965,046 for the year ended December 31, 2021. This increase was primarily driven by improvements in our business performance and the impact from acquisitions in subscriptions revenues, the impact from acquisitions in services revenues, and the overall positive foreign currency effects due to a weaker U.S. Dollar relative to our other functional currencies. We define business performance as our organic growth results inclusive of the impact from certain programmatic acquisitions, which generally are immaterial, individually and in the aggregate. On a constant currency basis, our revenues increased by 18.2% for the year ended December 31, 2021, as compared to the year ended December 31, 2020.

•Subscriptions. For the year ended December 31, 2021, subscriptions revenues increased by $133,534, or 19.7%, as compared to the year ended December 31, 2020. This increase was driven primarily by improvements in our business performance, $51,557 related to our acquisition of Seequent, and the positive foreign currency effects due to a weaker U.S. Dollar relative to our other functional currencies. On a constant currency basis, our subscriptions revenues increased by 17.6% for the year ended December 31, 2021 as compared to the year ended December 31, 2020.

Our growth in subscriptions was primarily due to expansion within our existing accounts, growth of 2% attributable to new accounts exclusive of acquisitions, most notability smaller- and medium-sized accounts, and the acquisition of Seequent. The improvements in business performance for the year ended December 31, 2021 was led by our civil design, SYNCHRO, ProjectWise, and geoprofessional products. For the year ended December 31, 2021, the impact of the Seequent acquisition includes organic growth within their existing accounts compared to the prior periods.

•Perpetual licenses. For the year ended December 31, 2021, perpetual licenses revenues decreased by $4,302, or 7.5%, as compared to the year ended December 31, 2020. This decrease was driven by a reduction in our business performance, partially offset by the impact of acquisitions and the positive foreign currency effects due to a weaker U.S. Dollar relative to our other functional currencies. On a constant currency basis, our perpetual licenses revenues decreased by 8.9% for the year ended December 31, 2021 as compared to the year ended December 31, 2020.

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•Services. For the year ended December 31, 2021, services revenues increased by $34,270, or 52.8%, as compared to the year ended December 31, 2020. This increase was driven primarily by the impact of acquisitions of $30,013, as well as the positive foreign currency effects due to a weaker U.S. Dollar relative to our other functional currencies. On a constant currency basis, our services revenues increased by 48.6% for the year ended December 31, 2021 as compared to the year ended December 31, 2020.

For the year ended December 31, 2021, the acquisition impact is attributable to several digital integrator businesses acquired throughout 2020 and 2021. Business performance continued to be impacted by COVID‑19 related delays in new projects and the redeployment of some services colleagues to support Success Services of our E365 subscription offering.

Revenues by Geographic Area

Revenues are allocated to individual countries based upon the location of users. Revenues by geographic area are as follows:

Comparison
Year EndedConstant
December 31,Currency
20212020Amount%%
Revenues by geographic area:
Americas$483,087$395,746$87,34122.1%21.4%
EMEA300,123254,03646,08718.1%14.2%
APAC181,836151,76230,07419.8%16.8%
Total revenues by geographic area$965,046$801,544$163,50220.4%18.2%

•Americas. For the year ended December 31, 2021, revenues from the Americas increased by $87,341, or 22.1%, as compared to the year ended December 31, 2020. This increase was driven primarily by improvements in our business performance in subscriptions revenues and the impact from acquisitions in subscriptions and services revenues. On a constant currency basis, our revenues from the Americas increased by 21.4% for the year ended December 31, 2021 as compared to the year ended December 31, 2020.

The constant currency growth in the Americas primarily reflects growth in recurring subscriptions revenues from our existing accounts in the U.S., the impact of the Seequent acquisition, and growth in services revenues in the U.S. and Canada from the acquisition of digital integrator businesses.

•EMEA. For the year ended December 31, 2021, revenues from EMEA increased by $46,087, or 18.1%, as compared to the year ended December 31, 2020. On a constant currency basis, our revenues from EMEA increased by 14.2% for the year ended December 31, 2021 as compared to the year ended December 31, 2020. The positive foreign currency effects were due to a weaker U.S. Dollar relative to our other functional currencies.

The constant currency growth primarily reflects growth in services revenues from the 2020 acquisitions of two digital integrator businesses in Europe. Constant currency growth also includes modest business growth in subscriptions revenues in Europe.

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•APAC. For the year ended December 31, 2021, revenues from APAC increased by $30,074, or 19.8%, as compared to the year ended December 31, 2020. This increase was driven primarily by improvements in our business performance in subscriptions revenues, the impact of the Seequent acquisition, and the positive foreign currency effects due to a weaker U.S. Dollar relative to our other functional currencies. On a constant currency basis, our revenues from APAC increased by 16.8% for the year ended December 31, 2021 as compared to the year ended December 31, 2020.

Excluding the impact of the Seequent acquisition, the constant currency growth was primarily due to expansion of our recurring subscriptions revenues in Australia, India, and China, net of attrition, for the year ended December 31, 2021.

Cost of Revenues

Comparison
Year EndedConstant
December 31,Currency
20212020Amount%%
Cost of subscriptions and licenses$124,321$95,803$28,51829.8%27.3%
Cost of services92,21871,35220,86629.2%24.4%
Total cost of revenues$216,539$167,155$49,38429.5%26.1%

For the year ended December 31, 2021, cost of revenues increased by $49,384, or 29.5%, to $216,539. This increase was driven by an increase in both cost of subscriptions and licenses and cost of services relative to the prior period. On a constant currency basis, total cost of revenues increased by 26.1% for the year ended December 31, 2021 as compared to the year ended December 31, 2020.

For the year ended December 31, 2021, cost of subscriptions and licenses increased 29.8%, or 27.3% in constant currency, as compared to the year ended December 31, 2020. On a constant currency basis, this increase was substantially due to an increase in headcount‑related costs of approximately $20,200, primarily driven by the redeployment of certain colleagues to our User Success group in support of Success Services available to accounts under programs such as our E365 subscription offering.

For the year ended December 31, 2021, cost of services increased by 29.2%, or 24.4% in constant currency, as compared to the year ended December 31, 2020. On a constant currency basis, this increase was substantially due to an increase in headcount‑related costs of approximately $15,800. The approximate $15,800 increase in headcount-related costs was primarily comprised of an increase in salaries and variable compensation costs of approximately $18,900, primarily driven by our digital integrator acquisitions, partially offset by a decrease in stock‑based compensation expense of approximately $1,700 and the realignment costs from the 2020 program of approximately $1,400.

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Operating Expenses

Comparison
Year EndedConstant
December 31,Currency
20212020Amount%%
Research and development$220,915$185,515$35,40019.1%16.5%
Selling and marketing162,240143,79118,44912.8%10.1%
General and administrative150,116113,27436,84232.5%31.1%
Deferred compensation plan95,04617794,869**
Amortization of purchased intangibles25,60115,35210,24966.8%61.3%
Expenses associated with initial public offering26,130(26,130)**
Total operating expenses$653,918$484,239$169,67935.0%32.8%

*Not meaningful

Research and development. For the year ended December 31, 2021, research and development expenses increased 19.1%, or 16.5% in constant currency, as compared to the year ended December 31, 2020. On a constant currency basis, this increase was primarily due to an increase in headcount-related costs of approximately $26,300. The approximate $26,300 increase in headcount-related costs was primarily comprised of an increase in salaries and variable compensation costs of approximately $34,400, primarily due to annual salary adjustments in 2021 combined with lower variable compensation costs in the prior period due to COVID‑19, and an increase in stock‑based compensation expense of approximately $7,400. Partially offsetting these increases in headcount-related costs is a decrease of approximately $14,700 in Bonus Plan related cash compensation due to the change in our Bonus Plan (see Note 11 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K), which allows participants within certain limitations to elect share delivery instead of cash compensation for their non-deferred incentive bonuses. Through the nine months ended September 30, 2020, non-deferred incentive bonuses earned under the Bonus Plan were paid in cash. The other component of the offsetting decrease in headcount-related costs is the realignment costs from the 2020 program of approximately $800.

Selling and marketing. For the year ended December 31, 2021, selling and marketing expenses increased 12.8%, or 10.1% in constant currency, as compared to the year ended December 31, 2020. On a constant currency basis, this increase was primarily due to an increase in headcount-related costs of approximately $12,400. The approximate $12,400 increase in headcount-related costs was primarily comprised of an increase in salaries and variable compensation costs of approximately $19,200, primarily due to annual salary adjustments in 2021 combined with lower variable compensation costs in the prior period due to COVID‑19, partially offset by the realignment costs from the 2020 program of approximately $6,000 and a decrease in stock‑based compensation expense of approximately $800.

General and administrative. For the year ended December 31, 2021, general and administrative expenses increased 32.5%, or 31.1% in constant currency, as compared to the year ended December 31, 2020. On a constant currency basis, this increase was primarily due to an increase in acquisition and other corporate initiatives expenses of approximately $17,200, primarily due to expenses related to the acquisition of Seequent, and an increase in headcount-related costs of approximately $15,000. The approximate $15,000 increase in headcount-related costs was primarily comprised of an increase in stock‑based compensation expense of approximately $12,300 and an increase in salaries and variable compensation costs of approximately $11,000, primarily due to annual salary adjustments in 2021 combined with lower variable compensation costs in the prior period due to COVID‑19. Partially offsetting these increases in headcount-related costs is a decrease of approximately $6,500 in Bonus Plan related cash compensation due to the change in our Bonus Plan as described above and the realignment costs from the 2020 program of approximately $1,800.

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Deferred compensation plan. For the year ended December 31, 2021, deferred compensation plan expenses increased by $94,869 as compared to the year ended December 31, 2020. This increase was primarily attributable to a one‑time $90,721 compensation charge recognized during the year ended December 31, 2021 as discussed further below and an increase of $4,148 attributable to changes in the deferred compensation liabilities which are marked to market at the end of each reporting period and recorded as an expense (income).

In August 2021, our board of directors approved an amendment to the DCP, which offered to certain active executives in the DCP a one‑time, short‑term election to reallocate a limited portion of their DCP holdings from phantom shares of the Company’s Class B Common Stock into other DCP phantom investment funds. The offer to reallocate was subject to a proration mechanism which adjusted the aggregate elections to a maximum of 1,500,000 phantom shares of the Company’s Class B Common Stock. This one‑time reallocation opportunity was offered only to certain active executives (but not to Directors or Bentley family members) in order to encourage retention, as otherwise these executives could only have materially diversified their investments in Company equity (primarily held in the DCP) by voluntarily terminating employment to trigger DCP distributions. These executives in aggregate accordingly diversified 24% of their phantom shares of the Company’s Class B Common Stock. While DCP participants’ investments in phantom shares remain equity classified, as they will be settled in shares of Class B Common Stock upon eventual distribution, the amendment and elections resulted in a change to liability classification for the reallocated phantom investments, as they will be settled in cash upon eventual distribution. As a result, during the year ended December 31, 2021, we recognized a one‑time compensation charge of $90,721 to Deferred compensation plan expenses in the consolidated statements of operations to record the reallocated deferred compensation plan liabilities at their fair value.

Amortization of purchased intangibles. For the year ended December 31, 2021, amortization of purchased intangibles increased by 66.8%, or 61.3% in constant currency, as compared to the year ended December 31, 2020. On a constant currency basis, this increase was primarily attributable to amortization from recently acquired purchased intangibles.

Expenses associated with initial public offering. For the year ended December 31, 2020, expenses associated with IPO include certain non-recurring costs relating to our IPO, consisting of the payment of underwriting discounts and commissions applicable to the sale of shares by the selling stockholders, professional fees, and other expenses. We completed our IPO on September 25, 2020. These fees were expensed in the period incurred.

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Interest Expense, Net

Year Ended
December 31,
20212020
Interest expense$(12,797)$(7,913)
Interest income306437
Interest expense, net$(12,491)$(7,476)
Year Ended
December 31,
20212020
Bank credit facility$(3,448)$(5,680)
Term loans(117)(502)
Interest rate swap(1,270)(696)
Convertible senior notes, coupon interest(1,899)
Amortization and write-off of deferred debt issuance costs(5,955)(985)
Other, net198387
Interest expense, net$(12,491)$(7,476)

For the year ended December 31, 2021, interest expense, net increased from the year ended December 31, 2020 primarily due to the increase in amortization and write‑off of deferred debt issuance costs and an increase in interest expense in connection with the convertible senior notes, partially offset by a lower outstanding average balance under the Credit Facility.

Other Income, Net

Year Ended
December 31,
20212020
Foreign exchange gain$827$22,919
Other income, net10,4042,027
Total other income, net$11,231$24,946

For the years ended December 31, 2021 and 2020, total other income, net consists of foreign exchange gains of $827 and $22,919, respectively. The foreign exchange gains derive primarily from U.S. Dollar denominated cash and cash equivalents, accounts receivable, and intercompany balances held by foreign subsidiaries. For the years ended December 31, 2021 and 2020, intercompany finance transactions denominated in U.S. Dollars resulted in unrealized foreign exchange (losses) gains of $(779) and $22,310, respectively.

For the year ended December 31, 2021, other income, net includes a gain from the change in fair value of our interest rate swap of $9,770. For the year ended December 31, 2020, other income, net includes a gain from the change in fair value of our interest rate swap of $347 and a gain from the change in fair value of acquisition contingent consideration of $1,340.

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(Benefit) Provision for Income Taxes

The income tax provisions for the years ended December 31, 2021 and 2020 were based on the effective income tax rates for those periods presented. For the years ended December 31, 2021 and 2020, we recognized an aggregate consolidated income tax (benefit) expense of $(3,448) and $38,625, respectively, for U.S. domestic and foreign income taxes. For the years ended December 31, 2021 and 2020, we recorded discrete tax benefits of $49,031 and $8,644, respectively, associated with stock‑based compensation. The effective income tax rate of (3.7)% on Income before income taxes of $93,329 for the year ended December 31, 2021 was lower than the effective income tax rate of 23.0% on Income before income taxes of $167,620 for the year ended December 31, 2020 primarily due to significant windfall tax benefits from stock‑based compensation, partially offset by the impact from officer compensation limitation provisions.

Net Income

Year Ended
December 31,
20212020
Net income$93,192$126,521

For the year ended December 31, 2021, net income decreased by $33,329 compared to the year ended December 31, 2020. The changes are due to the factors described above.

Adjusted EBITDA and Adjusted Net Income

Year Ended
December 31,
20212020
Adjusted EBITDA$324,948$266,376
Adjusted Net Income$266,940$192,812

For the year ended December 31, 2021, Adjusted EBITDA increased by $58,572 compared to the year ended December 31, 2020. For the years ended December 31, 2021 and 2020, Adjusted EBITDA as a percentage of total revenues was 33.7% and 33.2%, respectively.

For the year ended December 31, 2021, Adjusted Net Income increased by $74,128 compared to the year ended December 31, 2020. For the years ended December 31, 2021 and 2020, Adjusted Net Income as a percentage of total revenues was 27.7% and 24.1%, respectively.

For additional information, including the limitations of using non‑GAAP financial measures, and reconciliations of the non‑GAAP financial measures to the most directly comparable financial measures stated in accordance with U.S. GAAP, see the section titled “—Non‑GAAP Financial Measures.”

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Comparison of the Years Ended December 31, 2020 and 2019

Revenues

Comparison
Year EndedConstant
December 31,Currency
20202019Amount%%
Revenues:
Subscriptions$679,273$608,300$70,97311.7%11.0%
Perpetual licenses57,38259,693(2,311)(3.9)%(4.6)%
Subscriptions and licenses736,655667,99368,66210.3%9.6%
Services64,88968,661(3,772)(5.5)%(5.7)%
Total revenues$801,544$736,654$64,8908.8%8.2%

Total revenues increased by $64,890, or 8.8%, to $801,544 for the year ended December 31, 2020. For the year ended December 31, 2020, the increase was driven by improvements in our organic performance of $26,757, the impact from acquisitions of $33,463, and the positive foreign currency effects due to a weaker U.S. Dollar relative to our other functional currencies of $4,670. On a constant currency basis, our revenues increased by 8.2% for the year ended December 31, 2020 as compared to the year ended December 31, 2019.

•Subscriptions. For the year ended December 31, 2020, subscriptions revenues increased by $70,973, or 11.7%, as compared to the year ended December 31, 2019. This increase was driven primarily by improvements in our organic performance of $52,012, and to a lesser extent, the impact from acquisitions of $14,841, as well as the positive foreign currency effects due to a weaker U.S. Dollar relative to our other functional currencies of $4,120. On a constant currency basis, our subscriptions revenues increased by 11.0% for the year ended December 31, 2020 as compared to the year ended December 31, 2019.

For the year ended December 31, 2020, the increase in organic performance was primarily due to expansion within our existing accounts, as reflected by our recurring revenues dollar‑based net retention rate of 107% and approximately 2% of the increase was attributed to new accounts. Approximately 50% of our organic performance expansion was driven by ProjectWise and civil design products for the year ended December 31, 2020.

•Perpetual licenses. For the year ended December 31, 2020, perpetual licenses revenues decreased by $2,311, or 3.9%, as compared to the year ended December 31, 2019. This decrease was driven by a reduction in our organic performance of $4,427, partially offset by the impact from acquisitions of $1,706, as well as the positive foreign currency effects due to a weaker U.S. Dollar relative to our other functional currencies of $410. On a constant currency basis, our perpetual licenses revenues decreased by 4.6% for the year ended December 31, 2020 as compared to the year ended December 31, 2019.

We observed a decrease in organic performance for the year ended December 31, 2020 as certain accounts delayed purchase decisions or shifted spend to subscription solutions due to COVID‑19.

•Services. For the year ended December 31, 2020, services revenues decreased by $3,772, or 5.5%, as compared to the year ended December 31, 2019. This decrease was driven primarily by a reduction in our organic performance of $20,828, partially offset by the impact from acquisitions of $16,916, as well as the positive foreign currency effects due to a weaker U.S. Dollar relative to our other functional currencies of $140. On a constant currency basis, our services revenues decreased by 5.7% for the year ended December 31, 2020 as compared to the year ended December 31, 2019.

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For the year ended December 31, 2020, the decrease in organic performance was primarily due to the winding down or completion of several larger services projects during 2019 and 2020, COVID‑19 related delays of new projects while social distancing measures are in place, the inclusion of learning benefits in our subscription offerings, and the partial redeployment of our services colleagues to support Success Blueprints of our E365 subscription offering.

Revenues by Geographic Area

Revenues are allocated to individual countries based upon the location of the users. Revenues by geographic area are as follows:

Comparison
Year EndedConstant
December 31,Currency
20202019Amount%%
Revenues by geographic area:
Americas$395,746$356,331$39,41511.1%11.3%
EMEA254,036236,60217,4347.4%5.8%
APAC151,762143,7218,0415.6%4.4%
Total revenues by geographic area$801,544$736,654$64,8908.8%8.2%

•Americas. For the year ended December 31, 2020, revenues from the Americas increased by $39,415, or 11.1%, as compared to the year ended December 31, 2019. This increase was driven primarily by improvements in our organic performance of $18,002 and the impact from acquisitions of $22,226, partially offset by negative foreign currency effects due to a stronger U.S. Dollar relative to our other functional currencies of $813. On a constant currency basis, our revenues from the Americas increased by 11.3% for the year ended December 31, 2020 as compared to the year ended December 31, 2019.

The increase in organic performance was primarily due to expansion of our recurring subscription revenues from our existing accounts in the U.S. and Canada. Approximately 30% of our subscription‑related organic performance expansion was driven by ProjectWise for the year ended December 31, 2020.

•EMEA. For the year ended December 31, 2020, revenues from EMEA increased by $17,434, or 7.4%, as compared to the year ended December 31, 2019. This increase was driven by improvements in our organic performance of $3,168, the impact from acquisitions of $10,554, and the positive foreign currency effects due to a weaker U.S. Dollar relative to our other functional currencies of $3,712. On a constant currency basis, our revenues from EMEA increased by 5.8% for the year ended December 31, 2020 as compared to the year ended December 31, 2019.

The increase in organic performance was primarily due to expansion of our recurring subscription revenues throughout the region. Approximately 50% of our subscription‑related organic performance expansion was driven by ProjectWise for the year ended December 31, 2020.

•APAC. For the year ended December 31, 2020, revenues from APAC increased by $8,041, or 5.6%, as compared to the year ended December 31, 2019. This increase was driven by improvements in our organic performance of $5,587 and, to a lesser extent, the impact from acquisitions of $683 and the positive foreign currency effects due to a weaker U.S. Dollar relative to our other functional currencies of $1,771. On a constant currency basis, our revenues from APAC increased by 4.4% for the year ended December 31, 2020 as compared to the year ended December 31, 2019.

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For the year ended December 31, 2020, the increase in organic performance was primarily due to expansion of our recurring subscription revenues from our existing accounts in Australia, China, and South East Asia. Approximately 40% of our subscription‑related organic performance expansion was driven by ProjectWise and Offshore Structural Analysis products.

Cost of Revenues

Comparison
Year EndedConstant
December 31,Currency
20202019Amount%%
Cost of subscriptions and licenses$95,803$71,578$24,22533.8%32.9%
Cost of services71,35272,572(1,220)(1.7)%(1.5)%
Total cost of revenues$167,155$144,150$23,00516.0%15.6%

For the year ended December 31, 2020, cost of revenues increased by $23,005, or 16.0%, to $167,155. This increase was driven primarily by an increase in cost of subscriptions and licenses, partially offset by lower cost of services relative to the prior period. On a constant currency basis, total cost of revenues increased by 15.6% for the year ended December 31, 2020 as compared to the year ended December 31, 2019.

For the year ended December 31, 2020, cost of subscriptions and licenses increased 33.8%, or 32.9% in constant currency, as compared to the year ended December 31, 2019. On a constant currency basis, this increase was primarily due to an increase in headcount‑related costs, excluding stock‑based compensation expense, of approximately $8,500, an increase in stock‑based compensation expense of approximately $800, an increase in hosting costs of approximately $8,000, an increase in amortization expense for software and technology of approximately $2,200, and an increase in facility‑related costs of approximately $600.

For the year ended December 31, 2020, cost of services decreased by 1.7%, or 1.5% in constant currency, as compared to the year ended December 31, 2019. On a constant currency basis, the decrease was primarily due to a decrease in headcount‑related costs, excluding stock‑based compensation expense and incremental realignment costs from the 2020 program, of approximately $1,500 and a decrease in amortization of previously capitalized costs related to certain professional services projects of approximately $4,600, partially offset by an increase in stock‑based compensation expense of approximately $2,400, incremental realignment costs from the 2020 program of approximately $1,400, and an increase in facility‑related costs of approximately $1,400.

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Operating Expenses

Comparison
Year EndedConstant
December 31,Currency
20202019Amount%%
Research and development$185,515$183,552$1,9631.1%1.0%
Selling and marketing143,791155,294(11,503)(7.4)%(7.3)%
General and administrative113,27497,17216,10216.6%16.0%
Deferred compensation plan177408(231)(56.6)%(56.6)%
Amortization of purchased intangibles15,35214,2131,1398.0%7.3%
Expenses associated with initial public offering26,13026,130**
Total operating expenses$484,239$450,639$33,6007.5%7.4%

*Not meaningful

Research and development. For the year ended December 31, 2020, research and development expenses increased 1.1%, or 1.0% in constant currency, as compared to the year ended December 31, 2019. On a constant currency basis, the increase was primarily due to an increase in stock‑based compensation expense of approximately $8,900 and incremental realignment costs from the 2020 program of approximately $800, partially offset by a decrease in headcount-related costs, excluding stock‑based compensation expense and incremental realignment costs from the 2020 program, of approximately $7,300 due to COVID‑19 related modification to colleague travel and variable compensation plans.

Selling and marketing. For the year ended December 31, 2020, selling and marketing expenses decreased 7.4%, or 7.3% in constant currency, as compared to the year ended December 31, 2019. On a constant currency basis, this decrease was primarily due to a decrease in headcount-related costs, excluding stock‑based compensation expense and incremental realignment costs from the 2020 program, of approximately $16,700 due to COVID‑19 related modification to colleague travel and variable compensation plans and a reduction in promotional costs of $5,000, substantially from rationalizing our marketing spend and shifting to virtual events given the evolving business environment as a result of COVID‑19, partially offset by an increase in stock‑based compensation expense of approximately $4,400 and incremental realignment costs from the 2020 program of approximately $6,000.

General and administrative. For the year ended December 31, 2020, general and administrative expenses increased 16.3%, or 16.0% in constant currency, as compared to the year ended December 31, 2019. On a constant currency basis, the increase was primarily due to an increase in headcount-related costs, excluding stock‑based compensation expense and incremental realignment costs from the 2020 program, of approximately $4,000, an increase in stock‑based compensation expense of approximately $8,100, incremental realignment costs from the 2020 program of approximately $1,800, and an increase in acquisition and other corporate initiatives expenses of $2,300.

Deferred compensation plan. For the year ended December 31, 2020, deferred compensation plan expenses decreased by $231, or 56.6%, as compared to the year ended December 31, 2019. This decrease was attributable to changes in the deferred compensation liabilities which are marked to market at the end of each reporting period and recorded as an expense (income).

Amortization of purchased intangibles. For the year ended December 31, 2020, amortization of purchased intangibles increased by 8.0%, or 7.3% in constant currency, as compared to the year ended December 31, 2019. The increase was primarily attributable to acquisitions that closed in 2020.

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Expenses associated with initial public offering. For the year ended December 31, 2020, expenses associated with IPO included certain non‑recurring costs relating to our IPO, consisting of the payment of underwriting discounts and commissions applicable to the sale of shares by the selling stockholders, professional fees, and other expenses. We completed our IPO on September 25, 2020. These fees were expensed in the period incurred.

Interest Expense, Net

Year Ended
December 31,
20202019
Interest expense$(7,913)$(9,731)
Interest income4371,532
Interest expense, net$(7,476)$(8,199)
Year Ended
December 31,
20202019
Bank credit facility$(5,680)$(8,971)
Term loan(502)
Interest rate swap(696)
Amortization and write-off of deferred debt issuance costs(985)(553)
Other, net3871,325
Interest expense, net$(7,476)$(8,199)

For the year ended December 31, 2020, net interest expense decreased from the year ended December 31, 2019 primarily due to a lower average interest rate, partially offset by a higher outstanding average balance under the Credit Facility, which includes the term loan of $125,000 we entered into on September 2, 2020 via the First Amendment to the Credit Facility (the “2020 Term Loan”) and subsequently repaid in November 2020.

Other Income (Expense), Net

Year Ended
December 31,
20202019
Foreign exchange gain (loss)$22,919$(5,591)
Other income, net2,02734
Total other income (expense), net$24,946$(5,557)

For the years ended December 31, 2020 and 2019, other income (expense), net primarily consists of foreign exchange gains (losses) of $22,919 and $(5,591), respectively. The foreign exchange gains (losses) derive primarily from U.S. Dollar denominated cash and cash equivalents, accounts receivable, and intercompany balances held by foreign subsidiaries. For the years ended December 31, 2020 and 2019, intercompany finance transactions denominated in U.S. Dollars resulted in unrealized foreign exchange gains (losses) of $22,310 and $(5,270), respectively.

For the year ended December 31, 2020, other income, net also includes a gain from the change in fair value of our interest rate swap of $347 and a gain from the change in fair value of acquisition contingent consideration of $1,340.

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(Provision) Benefit for Income Taxes

The income tax provisions for the years ended December 31, 2020 and 2019 were based on the effective income tax rates applicable for those periods. For the years ended December 31, 2020 and 2019, we recognized an aggregate consolidated income tax expense of $38,625 and $23,738, respectively, for U.S. domestic and foreign income taxes. For the years ended December 31, 2020 and 2019, we recorded a discrete tax benefit of $8,644 and $2,940, respectively, associated with stock‑based compensation. The effective income tax rate of 23.0% for the year ended December 31, 2020 was higher than the effective income tax rate of 18.5% for the year ended December 31, 2019 primarily due to officer compensation limitation provisions resulting from our IPO, which went effective during the third quarter of 2020, and the non‑deductibility of expenses associated with our IPO, partially offset by increased discrete windfall tax benefits from stock‑based compensation.

Net Income

Year Ended
December 31,
20202019
Net income$126,521$103,096

For the year ended December 31, 2020, net income increased by $23,425, or 22.7%, compared to the year ended December 31, 2019. The changes are due to the factors described above.

Adjusted EBITDA and Adjusted Net Income

Year Ended
December 31,
20202019
Adjusted EBITDA$266,376$188,537
Adjusted Net Income$192,812$135,357

For the year ended December 31, 2020, Adjusted EBITDA increased by $77,839 compared to the year ended December 31, 2019. For the years ended December 31, 2020 and 2019, Adjusted EBITDA as a percentage of total revenues was 33.2% and 25.6%, respectively.

For the year ended December 31, 2020, Adjusted Net Income increased by $57,455 compared to the year ended December 31, 2019. For the years ended December 31, 2020 and 2019, Adjusted Net Income as a percentage of total revenues was 24.1% and 18.4%, respectively.

For additional information, including the limitations of using non‑GAAP financial measures, and reconciliations of the non‑GAAP financial measures to the most directly comparable financial measures stated in accordance with U.S. GAAP, see the section titled “—Non‑GAAP Financial Measures.”

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Liquidity and Capital Resources:

Our primary source of operating cash is from the sale of subscriptions, perpetual licenses, and services. Our primary use of cash is payment of our operating costs, which consist primarily of colleague-related expenses, such as compensation and benefits, as well as general operating expenses for marketing, facilities, and overhead costs. In addition to operating expenses, we also use cash to pay quarterly dividends, to service our debt obligations, and for capital expenditures in support of our operations. We also use cash to fund our growth initiatives, which include acquisitions of software assets and businesses, and other investment activities of BSY Investments, including iTwin Ventures for which, over a period of approximately 5 years, we expect to invest up to $100 million of corporate venture capital funding for seed, early, and growth stage technology companies with promising and emerging opportunities for infrastructure digital twin solutions strategically relevant to our business. In connection with the acquisition of Seequent in June 2021, we used readily available cash, including a portion of the net proceeds from the 2026 Notes, and borrowings under our Credit Facility to fund the cash component of the transaction. As described further below, we used $25,875 of the net proceeds from the sale of the 2027 Notes to pay the premiums of the capped call options, and $536,062 to repay outstanding indebtedness under the Credit Facility and to pay related fees and expenses. We used $25,530 of the net proceeds from the sale of the 2026 Notes to pay the premiums of the capped call options, and approximately $250,500 to repay outstanding indebtedness under the Credit Facility and to pay related fees and expenses. We used the remainder of the net proceeds from the sale of the 2026 Notes for general corporate purposes and towards funding certain acquisitions, including Seequent.

Our cash and cash equivalent balances are concentrated in a few locations around the world, with substantial amounts held outside of the U.S. As of December 31, 2021 and 2020, 48% and 94%, respectively, of our total cash and cash equivalents were located outside of the U.S. We intend to continue to permanently reinvest these funds outside of the U.S. and current plans do not demonstrate a need to repatriate them to fund our U.S. operations. We expect to meet our U.S. liquidity needs through ongoing cash flows or external borrowings including available liquidity under the Credit Facility described below. We regularly review our capital structure and consider a variety of potential financing alternatives and planning strategies to ensure that we have the proper liquidity available in the locations in which it is needed and to fund our operations and growth investments with cash that has not been permanently reinvested outside the U.S.

We believe that existing cash and cash equivalent balances, together with cash generated from operations, and liquidity under the Credit Facility, will be sufficient to meet our domestic and international working capital and capital expenditure requirements through the next twelve months. However, our future capital requirements may be materially different than those currently planned in our budgeting and forecasting activities and depend on many factors, including our rate of revenue growth, the timing and extent of spending on research and development, the expansion of our sales and marketing activities, the timing of new product introductions, market acceptance of our products, competitive factors, currency fluctuations, and overall economic conditions, globally. To the extent that current and anticipated future sources of liquidity are insufficient to fund our future business activities and requirements, we may be required to seek additional equity or debt financing. The sale of additional equity would result in additional dilution to our stockholders, while the incurrence of debt financing, including convertible debt, would result in debt service obligations. Such debt instruments also could introduce covenants that might restrict our operations. We cannot provide assurance that we could obtain additional financing on favorable terms or at all.

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Cash and cash equivalents

We consider all highly liquid investments with an original maturity of three months or less at the date of purchase to be cash equivalents. Our cash and cash equivalents consisted of cash held in checking accounts and money market funds maintained at various financial institutions. The following table presents our foreign and domestic holdings of cash and cash equivalents:

December 31,
20212020
Cash and cash equivalents:
Held domestically$170,267$7,861
Held by foreign subsidiaries159,070114,145
Total cash and cash equivalents$329,337$122,006

The amount of cash and cash equivalents held by foreign subsidiaries is subject to translation adjustments caused by changes in foreign currency exchange rates as of the end of each respective reporting period, the offset to which is recorded in Accumulated other comprehensive loss on our consolidated balance sheets.

Bank Credit Facility

On January 25, 2021, we entered into the Second Amendment to the Amended and Restated Credit Agreement dated December 19, 2017, which increased the senior secured revolving loan facility from $500,000 to $850,000 and extended the maturity date from December 18, 2022 to November 15, 2025. In connection with the Second Amendment, certain lenders exited the Credit Facility. We performed an extinguishment versus modification assessment on a lender‑by‑lender basis resulting in the write‑off of unamortized debt issuance costs of $353 and the capitalization of fees paid to lenders and third parties of $3,577. Debt issuance costs are amortized to interest expense through the maturity date of November 15, 2025.

On June 22, 2021, we entered into the Third Amendment to the Credit Facility, which increased the aggregate amount of approved convertible debt to permit the issuance and sale of additional convertible senior notes. See the section titled “—Convertible Senior Notes—2027 Notes” below.

On December 22, 2021, we entered into the Fourth Amendment to the Credit Facility, which provided for a new $200,000 senior secured term loan with a maturity of November 15, 2025 and included certain other amendments. The 2021 Term Loan requires principal repayment at the end of each calendar quarter. Beginning with March 31, 2022 and ending with December 31, 2023, we are required to repay $1,250 per quarter. Beginning with March 31, 2024 and ending with the last such date prior to the maturity date, we are required to repay $2,500 per quarter. We incurred $540 of debt issuance costs related to the 2021 Term Loan. As of December 31, 2021, $45 of the transaction costs were recorded in Accruals and other current liabilities in the consolidated balance sheet. We used borrowings under the 2021 Term Loan to pay down borrowings under the swingline sub‑facility and revolving facility under the Credit Facility.

Under the 2021 Term Loan, we may make either Euro currency or non-Euro currency interest rate elections. Interest on the Euro currency borrowings bear a base interest rate of LIBOR, plus a spread ranging from 100 basis points (“bps”) to 200 bps as determined by our net leverage ratio. Under the non-Euro currency elections, the 2021 Term Loan bears a base interest rate of the highest of (i) the prime rate, (ii) the overnight bank funding effective rate plus 50 bps, or (iii) LIBOR plus 100 bps, plus a spread ranging from 0 bps to 100 bps as determined by our net leverage ratio.

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On September 2, 2020, we entered into the First Amendment to the Credit Facility, which provided a new term loan of $125,000 with a maturity of December 18, 2022 and included certain other amendments, including the addition of a mandatory prepayment provision requiring us to prepay borrowings under the Credit Facility in an aggregate amount equal to the net proceeds from any underwritten public offering by us, which prepayment shall be applied, first, to the 2020 Term Loan and, second, to any borrowings outstanding under the revolving facility under the Credit Facility without reducing the revolving commitments thereof. We used borrowings under the 2020 Term Loan and under the revolving facility under the Credit Facility to pay a special dividend declared by our board of directors on August 28, 2020. We incurred $432 of debt issuance costs related to the 2020 Term Loan. In November 2020, we used a portion of the net proceeds from our follow‑on public offering to repay the 2020 Term Loan. See Notes 10 and 13 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K.

In addition to the senior secured revolving loan facility, the Credit Facility also provides up to $50,000 of letters of credit and other incremental borrowings subject to availability, including a $85,000 U.S. Dollar swingline sub‑facility and a $200,000 incremental “accordion” sub‑facility. We had $150 of letters of credit and surety bonds outstanding as of December 31, 2021 and 2020. As of December 31, 2021 and 2020, we had $849,850 and $253,850 available under the Credit Facility.

Under the Credit Facility, we may make either Euro currency or non‑Euro currency interest rate elections. Interest on the Euro currency borrowings bear a base interest rate of the London Interbank Offered Rate (“LIBOR”) plus a spread ranging from 125 bps to 225 bps as determined by our net leverage ratio. Under the non‑Euro currency elections, Credit Facility borrowings bear a base interest rate of the highest of (i) the prime rate, (ii) the overnight bank funding effective rate plus 50 bps, or (iii) LIBOR plus 100 bps, plus a spread ranging from 25 bps to 125 bps as determined by our net leverage ratio. In addition, a commitment fee for the unused Credit Facility ranges from 20 bps to 30 bps as determined by our net leverage ratio.

Borrowings under the Credit Facility are guaranteed by all of our first tier domestic subsidiaries and are secured by a first priority security interest in substantially all of our and the guarantors’ U.S. assets and 65% of the stock of their directly owned foreign subsidiaries. The Credit Facility contains both affirmative and negative covenants, including maximum net leverage ratios. As of December 31, 2021 and 2020, we were in compliance with all covenants in our Credit Facility.

Interest rate risk associated with the Credit Facility is managed through an interest rate swap which we executed on March 31, 2020. The interest rate swap has an effective date of April 2, 2020 and a termination date of April 2, 2030. Under the terms of the interest rate swap, we fixed our LIBOR borrowing rate at 0.73% on a notional amount of $200,000. The interest rate swap is not designated as a hedging instrument for accounting purposes. We account for the interest rate swap as either an asset or a liability in the consolidated balance sheets and carry the derivative at fair value. Gains and losses from the change in fair value are recognized in Other income (expense), net, in the consolidated statements of operations. As of December 31, 2021 and 2020, we recorded a swap related asset at fair value of $10,117 and $347, respectively, in Other assets in the consolidated balance sheets.

The weighted average interest rate under the Credit Facility was 2.03%, 1.92%, and 3.47% for the years ended December 31, 2021, 2020, and 2019, respectively.

The agreement governing the Credit Facility contains customary events of default, including, without limitation, payment defaults, breaches of representations and warranties, covenants defaults, cross-defaults to certain other indebtedness in excess of $50,000, certain events of bankruptcy and insolvency, judgment defaults in excess of $10,000, failure of any security document supporting the Credit Facility to be in full force and effect, and a change of control.

Voluntary prepayments of amounts outstanding under the Credit Facility, in whole or in part, are permitted at any time, so long as we give notice as required by the Credit Facility. However, if prepayment is made with respect to a LIBOR‑based loan and the prepayment is made on a date other than an interest payment date, we must pay customary breakage costs.

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Convertible Senior Notes

2027 Notes. On June 28, 2021, we completed a private offering of $575,000 of 0.375% convertible senior notes due 2027. The 2027 Notes were issued pursuant to an indenture, dated as of June 28, 2021, between the Company and Wilmington Trust, National Association, as trustee (the “2027 Trustee”) (the “2027 Indenture”). Interest will accrue from June 28, 2021 and will be payable semi‑annually in arrears in cash on January 1 and July 1 of each year, with the first payment due on January 1, 2022. The 2027 Notes will mature on July 1, 2027, unless earlier converted, redeemed or repurchased. We incurred $15,065 of expenses in connection with the 2027 Notes offering consisting of transaction costs. We used $25,875 of the net proceeds from the sale of the 2027 Notes to pay the premiums of the capped call options described further below, and $536,062 to repay outstanding indebtedness under the Credit Facility and to pay related fees and expenses.

Prior to April 1, 2027, the 2027 Notes will be convertible at the option of the holder only under the following circumstances: (1) during any calendar quarter (and only during such quarter) commencing after the calendar quarter ending on September 30, 2021, if the last reported sale price per share of our Class B Common Stock exceeds 130% of the conversion price for each of at least 20 trading days, whether or not consecutive, during the 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding calendar quarter; (2) during the five consecutive business days immediately after any ten consecutive trading day period (such ten consecutive trading day period, the “measurement period”) in which the trading price per $1 principal amount of 2027 Notes for each trading day of the measurement period was less than 98% of the product of the last reported sale price per share of our Class B Common Stock on such trading day and the conversion rate on such trading day; (3) upon the occurrence of certain corporate events or distributions on our Class B Common Stock, as described in the 2027 Indenture; and (4) if we call the 2027 Notes for redemption. On or after April 1, 2027 until 5:00 p.m., New York City time, on the second scheduled trading day immediately before the maturity date, the 2027 Notes will be convertible at the option of the holder at any time.

We will settle conversions by paying or delivering, as applicable, cash, shares of our Class B Common Stock or a combination of cash and shares of our Class B Common Stock, at our election, based on the applicable conversion rate. The initial conversion rate is 12.0153 shares of our Class B Common Stock per $1 principal amount of 2027 Notes, which represents an initial conversion price of approximately $83.23 per share, and is subject to adjustment as described in the 2027 Indenture. If a “make-whole fundamental change” (as defined in the 2027 Indenture) occurs, then we will, in certain circumstances, increase the conversion rate for a specified period of time.

We will have the option to redeem the 2027 Notes in whole or in part at any time on or after July 5, 2024 and on or before the 40th scheduled trading day immediately before the maturity date if the last reported sale price per share of our Class B common stock exceeds 130% of the conversion price on (1) each of at least 20 trading days, whether or not consecutive, during any 30 consecutive trading days ending on, and including, the trading day immediately before the date we send the related redemption notice; and (2) the trading day immediately before the date we send such notice. The redemption price will be equal to the principal amount of the 2027 Notes to be redeemed, plus accrued and unpaid interest, if any, to, but excluding, the redemption date.

Upon a fundamental change (as defined in the 2027 Indenture), holders may, subject to certain exceptions, require us to purchase their 2027 Notes in whole or in part for cash at a price equal to the principal amount of the 2027 Notes to be purchased, plus accrued and unpaid interest, if any, to, but excluding, the fundamental change repurchase date (as defined in the 2027 Indenture). In addition, upon a Make‑Whole Fundamental Change (as defined in the 2027 Indenture), we will, under certain circumstances, increase the applicable conversion rate for a holder that elects to convert its 2027 Notes in connection with such Make‑Whole Fundamental Change. No adjustment to the conversion rate will be made if the stock price in such Make‑Whole Fundamental Change is either less than $61.65 per share or greater than $325.00 per share. We will not increase the conversion rate to an amount that exceeds 16.2206 shares per $1 principal amount of 2027 Notes, subject to adjustment. The 2027 Indenture also contains a customary merger covenant.

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Under the 2027 Indenture, the 2027 Notes may be accelerated upon the occurrence of certain customary events of default. If certain bankruptcy and insolvency‑related events of default with respect to us occur, the principal of, and accrued and unpaid interest on, all of the then outstanding 2027 Notes shall automatically become due and payable. If any other event of default occurs and is continuing, the 2027 Trustee by notice to us, or the holders of the 2027 Notes of at least 25% in principal amount of the outstanding 2027 Notes by notice to us and the 2027 Trustee, may declare the principal of, and accrued and unpaid interest on, all of the then outstanding 2027 Notes to be due and payable. Notwithstanding the foregoing, the 2027 Indenture provides that, to the extent we elect, the sole remedy for an event of default relating to certain failures by us to comply with reporting covenant in the 2027 Indenture consists exclusively of the right to receive additional interest on the 2027 Notes.

We early adopted ASU 2020‑06 as of January 1, 2021 and concluded the 2027 Notes will be accounted for as debt, with no bifurcation of the embedded conversion feature. Transaction costs were recorded as a direct deduction from the related debt liability in the consolidated balance sheet and are amortized to interest expense over the term of the 2027 Notes. The effective interest rate for the 2027 Notes is 0.864%.

As of December 31, 2021, none of the conditions of the 2027 Notes to early convert has been met.

The 2027 Notes are our senior, unsecured obligations that rank senior in right of payment to our future indebtedness that is expressly subordinated to the 2027 Notes, rank equally in right of payment with our existing and future senior unsecured indebtedness that is not so subordinated (including our 2026 Notes), effectively subordinated to our existing and future secured indebtedness (including obligations under our senior secured credit facilities), to the extent of the value of the collateral securing such indebtedness, and structurally subordinated to all existing and future indebtedness and other liabilities (including trade payables and preferred equity (to the extent we are not a holder thereof)) of our subsidiaries. The 2027 Notes contain both affirmative and negative covenants. As of December 31, 2021, we were in compliance with all covenants in the 2027 Notes.

Capped Call Options. In connection with the pricing of the 2027 Notes, we entered into capped call options with certain of the initial purchasers or their respective affiliates and certain other financial institutions. We incurred $50 of expenses in connection with the capped call options. The capped call options are expected to reduce potential dilution to our Class B Common Stock upon any conversion of 2027 Notes and/or offset any cash payments we are required to make in excess of the principal amount of converted notes, as the case may be, with such reduction and/or offset subject to a cap. The cap price of the capped call options is initially $95.5575 per share, which represents a premium of 55% above the last reported sale price per share of our Class B Common Stock on the Nasdaq Global Select Market on June 23, 2021 and is subject to customary adjustments under the terms of the capped call options.

The capped call options were entered into in conjunction with the issuance of the 2027 Notes, however, they are legally separate agreements that can be separately exercised, with the receipt of shares under the capped call options having no effect on the 2027 Notes, and are legally detachable. As the capped call options are both legally detachable and separately exercisable from the 2027 Notes, we account for the capped call options separately from the 2027 Notes. The capped call options are indexed to our own common stock and classified in stockholders’ equity. As such, the premiums paid for the capped call options have been included as a net reduction to Additional paid-in capital in the consolidated balance sheet.

2026 Notes. On January 26, 2021, we completed a private offering of $690,000 of 0.125% convertible senior notes due 2026. The 2026 Notes were issued pursuant to an indenture, dated as of January 26, 2021, between the Company and Wilmington Trust, National Association, as trustee (the “2026 Trustee”) (the “2026 Indenture”). Interest will accrue from January 26, 2021 and will be payable semi‑annually in arrears in cash on January 15 and July 15 of each year, with the first payment due on July 15, 2021. The 2026 Notes will mature on January 15, 2026, unless earlier converted, redeemed or repurchased. We incurred $18,055 of expenses in connection with the 2026 Notes offering consisting of transaction costs. We used $25,530 of the net proceeds from the sale of the 2026 Notes to pay the premiums of the capped call options described further below, and approximately $250,500 to repay outstanding indebtedness under the Credit Facility and to pay related fees and expenses. We used the remainder of the net proceeds from the sale of the 2026 Notes for general corporate purposes and towards funding certain acquisitions, including Seequent.

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Prior to October 15, 2025, the 2026 Notes will be convertible at the option of the holder only under the following circumstances: (1) during any calendar quarter (and only during such quarter) commencing after the calendar quarter ending on June 30, 2021, if the last reported sale price per share of our Class B Common Stock exceeds 130% of the conversion price for each of at least 20 trading days, whether or not consecutive, during the 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding calendar quarter; (2) during the five consecutive business days immediately after any ten consecutive trading day period (such ten consecutive trading day period, the “measurement period”) in which the trading price per $1 principal amount of 2026 Notes for each trading day of the measurement period was less than 98% of the product of the last reported sale price per share of our Class B Common Stock on such trading day and the conversion rate on such trading day; (3) upon the occurrence of certain corporate events or distributions on our Class B Common Stock, as described in the 2026 Indenture; and (4) if we call the 2026 Notes for redemption. On or after October 15, 2025 until 5:00 p.m., New York City time, on the second scheduled trading day immediately before the maturity date, the 2026 Notes will be convertible at the option of the holder at any time.

We will settle conversions by paying or delivering, as applicable, cash, shares of our Class B Common Stock or a combination of cash and shares of our Class B Common Stock, at our election, based on the applicable conversion rate. The initial conversion rate is 15.5925 shares of our Class B Common Stock per $1 principal amount of 2026 Notes, which represents an initial conversion price of approximately $64.13 per share, and is subject to adjustment as described in the 2026 Indenture. If a “make-whole fundamental change” (as defined in the 2026 Indenture) occurs, then we will, in certain circumstances, increase the conversion rate for a specified period of time.

We will have the option to redeem the 2026 Notes in whole or in part at any time on or after January 20, 2024 and on or before the 40th scheduled trading day immediately before the maturity date if the last reported sale price per share of our Class B common stock exceeds 130% of the conversion price on (1) each of at least 20 trading days, whether or not consecutive, during any 30 consecutive trading days ending on, and including, the trading day immediately before the date we send the related redemption notice; and (2) the trading day immediately before the date we send such notice. The redemption price will be equal to the principal amount of the 2026 Notes to be redeemed, plus accrued and unpaid interest, if any, to, but excluding, the redemption date.

Upon a fundamental change (as defined in the 2026 Indenture), holders may, subject to certain exceptions, require us to purchase their 2026 Notes in whole or in part for cash at a price equal to the principal amount of the 2026 Notes to be purchased, plus accrued and unpaid interest, if any, to, but excluding, the fundamental change repurchase date (as defined in the 2026 Indenture). In addition, upon a Make‑Whole Fundamental Change (as defined in the 2026 Indenture), we will, under certain circumstances, increase the applicable conversion rate for a holder that elects to convert its 2026 Notes in connection with such Make‑Whole Fundamental Change. No adjustment to the conversion rate will be made if the stock price in such Make‑Whole Fundamental Change is either less than $44.23 per share or greater than $210.00 per share. We will not increase the conversion rate to an amount that exceeds 22.6090 shares per $1 principal amount of 2026 Notes, subject to adjustment. The 2026 Indenture also contains a customary merger covenant.

Under the 2026 Indenture, the 2026 Notes may be accelerated upon the occurrence of certain customary events of default. If certain bankruptcy and insolvency‑related events of default with respect to us occur, the principal of, and accrued and unpaid interest on, all of the then outstanding 2026 Notes shall automatically become due and payable. If any other event of default occurs and is continuing, the 2026 Trustee by notice to us, or the holders of the 2026 Notes of at least 25% in principal amount of the outstanding 2026 Notes by notice to us and the 2026 Trustee, may declare the principal of, and accrued and unpaid interest on, all of the then outstanding 2026 Notes to be due and payable. Notwithstanding the foregoing, the 2026 Indenture provides that, to the extent we elect, the sole remedy for an event of default relating to certain failures by us to comply with reporting covenant in the 2026 Indenture consists exclusively of the right to receive additional interest on the 2026 Notes.

As previously discussed, we early adopted ASU 2020‑06 as of January 1, 2021 and concluded the 2026 Notes will be accounted for as debt, with no bifurcation of the embedded conversion feature. Transaction costs were recorded as a direct deduction from the related debt liability in the consolidated balance sheet and are amortized to interest expense over the term of the 2026 Notes. The effective interest rate for the 2026 Notes is 0.658%.

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As of December 31, 2021, none of the conditions of the 2026 Notes to early convert has been met.

The 2026 Notes are our senior, unsecured obligations that rank senior in right of payment to our future indebtedness that is expressly subordinated to the 2026 Notes, rank equally in right of payment with our existing and future senior unsecured indebtedness that is not so subordinated (including our 2027 Notes, see the section titled “—2027 Notes” below), effectively subordinated to our existing and future secured indebtedness (including obligations under our senior secured credit facilities), to the extent of the value of the collateral securing such indebtedness, and structurally subordinated to all existing and future indebtedness and other liabilities (including trade payables and preferred equity (to the extent we are not a holder thereof)) of our subsidiaries. The 2026 Notes contain both affirmative and negative covenants. As of December 31, 2021, we were in compliance with all covenants in the 2026 Notes.

Capped Call Options. In connection with the pricing of the 2026 Notes, we entered into capped call options with certain of the initial purchasers or their respective affiliates and certain other financial institutions. We incurred $150 of expenses in connection with the capped call options. The capped call options are expected to reduce potential dilution to our Class B Common Stock upon any conversion of 2026 Notes and/or offset any cash payments we are required to make in excess of the principal amount of converted notes, as the case may be, with such reduction and/or offset subject to a cap. The cap price of the capped call options is initially $72.9795 per share, which represents a premium of 65% above the last reported sale price per share of our Class B Common Stock on the Nasdaq Global Select Market on January 21, 2021 and is subject to customary adjustments under the terms of the capped call options.

The capped call options were entered into in conjunction with the issuance of the 2026 Notes, however, they are legally separate agreements that can be separately exercised, with the receipt of shares under the capped call options having no effect on the 2026 Notes, and are legally detachable. As the capped call options are both legally detachable and separately exercisable from the 2026 Notes, we account for the capped call options separately from the 2026 Notes. The capped call options are indexed to our own common stock and classified in stockholders’ equity. As such, the premiums paid for the capped call options have been included as a net reduction to Additional paid-in capital in the consolidated balance sheet.

Comparison of the Year Ended December 31, 2021 and 2020

The following table summarizes our cash flow activities for the years ended December 31, 2021 and 2020:

Year Ended December 31,
20212020
Net Cash Provided By (Used In):
Operating activities$288,024$258,340
Investing activities(1,056,603)(117,333)
Financing activities982,582(136,511)

Operating activities

Net cash provided by operating activities was $288,024 for the year ended December 31, 2021. Compared to the prior year, net cash provided by operating activities was higher by $29,684 due to a net increase in non‑cash adjustments of $22,933 and a net increase in net cash flows from the change in operating assets and liabilities of $40,080, partially offset by a decrease in net income of $33,329. The net increase in cash flows from the change in operating assets and liabilities was primarily due to the increase in deferred compensation plan liabilities (as previously discussed above), partially offset by an increase in accounts receivable due to revenue growth and the timing of collections from accounts.

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For the year ended December 31, 2020, net cash provided by operating activities was $258,340 due to net income of $126,521 increased by $60,747 of non‑cash adjustments and $71,072 from changes in operating assets and liabilities.

Investing activities

Net cash used in investing activities was $1,056,603 for the year ended December 31, 2021, primarily due to $17,539 related to purchases of property and equipment and investment in capitalized software and $1,034,983 in acquisition related payments, net of cash acquired.

For the year ended December 31, 2020, net cash used in investing activities was $117,333, primarily due to $16,447 related to purchases of property and equipment and investment in capitalized software and $93,032 in acquisition related payments, net of cash acquired.

Financing activities

Net cash provided by financing activities was $982,582 for the year ended December 31, 2021. Compared to the prior year, net cash provided by financing activities increased by $1,119,093, primarily due to the net proceeds from the convertible senior notes of $1,233,377 in 2021 and a decrease in payments for dividends of $389,250, partially offset by $294,429 of proceeds from our follow‑on public offering, net of expenses, in 2020, a decrease in net borrowings of $58,745 under the Credit Facility, and the purchase of capped call options of $51,605 in 2021.

For the year ended December 31, 2020, net cash used in financing activities was $136,511, primarily due to payments of dividends of $422,646, partially offset by $294,429 of proceeds from our follow‑on public offering, net of expenses.

Subsequent Event after December 31, 2021

On January 31, 2022, we completed the acquisition of Power Line Systems, a leader in software for the design of overhead electric power transmission lines and their structures, for approximately $700,000 in cash, net of cash acquired, and subject to customary adjustments including for working capital. We used readily available cash and borrowings under our bank credit facility to fund the transaction. The acquisition is not expected to be material to our consolidated statements of operations. The acquisition is expected to be material to our financial position and cash flows.

Contractual Obligations and Other Commitments:

As of December 31, 2021, our future contractual obligations were related to debt (see Note 10), leases (see Note 8), purchase obligations (see Note 18), deferred compensation plan liabilities (see Note 12), and contingent and non‑contingent consideration from acquisitions (see Note 4). For information about those obligations, see the above referenced notes to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K, which are incorporated by reference into this section. As of December 31, 2021, our purchase obligations were $50,329, with $34,889 expected to be paid within one year and $15,440 thereafter. Purchase obligations include the non‑cancelable future cash purchase commitment for services related to the provisioning of our hosted software solutions. Our purchase obligations are in addition to amounts included in current liabilities and prepaid expenses in our consolidated balance sheet.

As noted above, on January 31, 2022, we completed the acquisition of Power Line Systems for approximately $700,000 in cash, net of cash acquired, and subject to customary adjustments including for working capital. We used readily available cash and borrowings under our bank credit facility to fund the transaction.

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Critical Accounting Policies and Estimates:

Our consolidated financial statements are prepared in conformity with U.S. GAAP. In preparing our consolidated financial statements, we make assumptions, judgments, and estimates that can have a significant impact on amounts reported in the consolidated financial statements. We base our assumptions, judgments, and estimates on historical experience and various other factors that we believe to be reasonable under the circumstances. Actual results could differ materially from these estimates under different assumptions or conditions. We regularly reevaluate our assumptions, judgments, and estimates. Our significant accounting policies are described in Note 1 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K.

An accounting policy is deemed to be critical if it requires an accounting estimate to be made based on assumptions about matters that are highly uncertain at the time the estimate is made, if different estimates reasonably could have been used, or if changes in the estimate that are reasonably possible could materially impact the financial statements. We believe that the following critical accounting policies affect the more significant judgments and estimates used in the preparation of our consolidated financial statements.

Revenue recognition. We recognize revenue in accordance with Topic 606. For a full description of our revenue accounting policy, see Note 1 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K. We generate revenues from subscriptions, perpetual licenses, and services.

Our contracts with customers may include promises to transfer licenses (perpetual or term‑based), maintenance, and services to a user. Judgment is required to determine if the promises are separate performance obligations, and if so, the allocation of the transaction price to each performance obligation. When an arrangement includes multiple performance obligations which are concurrently delivered and have the same pattern of transfer to the customer, we account for those performance obligations as a single performance obligation. For contracts with more than one performance obligation, the transaction price is allocated among the performance obligations in an amount that depicts the relative SSP of each obligation. Judgment is required to determine the SSP for each distinct performance obligation. In instances where SSP is not directly observable, such as when we do not sell the product or service separately, we determine the SSP using information that may include market conditions and other observable inputs. We use a range of amounts to estimate SSP when we sell each of the products and services separately and need to determine whether there is a discount that should be allocated based on the relative SSP of the various products and services.

Our SELECT agreement provides users with perpetual licenses a right to exchange software for other eligible perpetual licenses on an annual basis upon renewal. We refer to this option as portfolio balancing and concluded that the portfolio balancing feature represents a material right resulting in the deferral of the associated revenue. Judgment is required to estimate the percentage of users who may elect to portfolio balance and considers inputs such as historical user elections. This feature is available once per term and must be exercised prior to the respective renewal term. We recognize the associated revenue upon election or when the portfolio balancing right expires. This right is included in the initial and subsequent renewal terms and we reestablish the revenue deferral for the material right upon the beginning of the renewal term. Portfolio balancing exchange rights are included in Deferred revenues in the consolidated balance sheets.

Business combinations. We allocate the fair value of the consideration transferred to the assets acquired and liabilities assumed, including trademarks, customer relationships, in‑process research and development, and acquired software and technology, based on their estimated fair values at the acquisition date. Any residual purchase price is recorded as goodwill. The purchase price allocation requires us to make significant estimates and assumptions, especially at the acquisition date, with respect to intangible assets and deferred revenue obligations.

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Although we believe the assumptions and estimates we have made are reasonable, they are based in part on historical experience and information obtained from the management of the acquired companies and are inherently uncertain. Examples of critical estimates used in valuing certain of the intangible assets we have acquired or may acquire in the future include but are not limited to:

•future expected cash flows from sales, maintenance agreements, and acquired developed technologies;

•the acquired company’s trade name and customer relationships as well as assumptions about the period of time the acquired trade name and customer relationships will continue to be used in our product portfolio;

•expected costs to develop the in-process research and development into commercially viable software and estimated cash flows from the projects when completed; and

•discount rates used to determine the present value of estimated future cash flows.

These estimates are inherently uncertain and unpredictable, and if different estimates were used the purchase price for the acquisition could be allocated to the acquired assets and liabilities differently from the allocation that we have made. In addition, unanticipated events and circumstances may occur, which may affect the accuracy or validity of such estimates, and, if such events occur, we may be required to record a charge against the value ascribed to an acquired asset or an increase in the amounts recorded for assumed liabilities.

Goodwill and other intangible assets. Intangible assets arise from acquisitions and principally consist of goodwill, trademarks, customer relationships, and acquired software and technology. Intangible assets, other than goodwill, are amortized on a straight‑line basis over their estimated useful lives, which range from three to ten years.

Goodwill consists of the excess of cost over the fair value of net assets acquired in business combinations. Goodwill is not amortized. Instead, it is tested annually for impairment, or more frequently if events occur or circumstances change that would more likely than not reduce its fair value below its carrying amount. We operate as a single reporting unit.

In testing for goodwill impairment, we may first qualitatively assess whether it is more likely than not (a likelihood of more than 50 percent) that a goodwill impairment exists. If it is determined that a quantitative assessment is required, we will recognize goodwill impairment as the difference between the carrying amount of the reporting unit and it’s fair value, but not to exceed the carrying amount of goodwill within the reporting unit. Based upon our most recent annual impairment assessment completed as of October 1, 2021, there were no indicators of impairment, and no impairment losses were recorded. There was no impairment of goodwill as a result of our annual impairment assessments conducted for the years ended December 31, 2021, 2020, and 2019.

Income taxes. We account for income taxes under the asset and liability method, which requires the recognition of deferred tax assets and liabilities for the expected future tax consequences of events that have been included in the consolidated financial statements. Under this method, deferred tax assets and liabilities are determined based on net operating loss carryforwards, credit carryforwards, and temporary differences between the financial statement and tax basis of assets and liabilities using enacted tax rates in effect for the year in which the items are expected to reverse. The effect of a change in tax rates on deferred tax assets and liabilities is recognized in income in the period of the enactment date.

We record net deferred tax assets to the extent we believe the assets will more likely than not be realized. In making such determination, we consider all available positive and negative evidence, including scheduled reversals of deferred tax liabilities, projected future taxable income, tax planning strategies, and recent financial operations. In the event we determine that we will not be able to realize deferred income tax assets in the future in excess of our net recorded amount, an adjustment to the valuation allowance would be recorded that would increase the provision for income taxes.

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We perform a quarterly assessment of the recoverability of the net deferred tax assets and believe that we will generate sufficient future taxable income in appropriate tax jurisdictions to realize the net deferred tax assets. Our judgment regarding future profitability may change due to future market conditions and other factors, including intercompany transfer pricing adjustments. Any change in future profitability may require material adjustments to these net deferred tax assets, resulting in a reduction in net income in the period when such determination is made. We believe our tax positions, including intercompany transfer pricing policies, are consistent with the tax laws in the jurisdictions in which we conduct our business. It is possible that these positions may be challenged by jurisdictional tax authorities and may have a significant impact on our effective tax rate.

We are subject to income taxes in the U.S. and in numerous foreign jurisdictions. As part of the process of preparing our consolidated financial statements, we are required to calculate our income tax expense based on taxable income by jurisdiction. There are many transactions and calculations about which the ultimate tax outcome is uncertain. As a result, our calculations involve estimates by management. Some of these uncertainties arise as a consequence of revenue‑sharing, cost‑reimbursement, and transfer pricing arrangements among related entities, and the differing tax treatment of revenue and cost items across various jurisdictions. If we were compelled to revise or to account differently for our arrangements, that revision could affect our tax liability. While we believe the positions we have taken are appropriate, we record reserves for taxes to address potential exposures involving tax positions that we believe could be challenged by taxing authorities. We record a benefit on a tax position when we determine that it is more likely than not that the position is sustainable upon examination, including resolution of any related appeals or litigation processes, based on the technical merits of the position. For tax positions that are more likely than not to be sustained, we measure the tax position at the largest amount of benefit that has a greater than 50 percent likelihood of being realized when it is effectively settled. We review the tax reserves as circumstances warrant and adjust the reserves as events occur that affect our potential liability for additional taxes. We follow the applicable guidance on derecognition, classification, interest and penalties, accounting in interim periods, disclosure, and transition with respect to uncertain tax positions. We recognize interest and penalties related to income taxes within the (Provision) benefit for income taxes line in the consolidated statements of operations. Accrued interest and penalties are included within the related tax liability line in the consolidated balance sheets.

Fair value of common stock prior to IPO. We were a privately held company with no active public market of our common stock prior to our IPO. Therefore, the estimated fair value of the common stock underlying our stock‑based awards granted prior to our IPO was determined by our board of directors, with input from management and contemporaneous third‑party valuations. We believe that our board of directors had the relevant experience and expertise to determine the fair value of our common stock prior to our IPO.

Prior to the IPO, and given the absence of a public trading market for our common stock, and in accordance with the American Institute of Certified Public Accountants practice guide, Valuation of Privately-Held-Company Equity Securities Issued as Compensation, our board of directors exercised reasonable judgment and considered numerous objective and subjective factors to determine the best estimate of the fair value of our common stock, including:

•contemporaneous independent valuations performed by an unrelated third-party valuation specialist;

•the nature of our business and its history;

•our operating and financial performance and forecast;

•present value of estimated future cash flows;

•the likelihood of achieving a liquidity event, such as an initial public offering, listing, or sale of our Company, given prevailing market condition and the nature and history of our business;

•any adjustment necessary to recognize a lack of marketability for our common stock;

•the market performance of comparable publicly traded companies; and

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•the U.S. and global capital market conditions.

In valuing our common stock, our board of directors determined the equity value of our business generally using the income approach and the market comparable approach valuation methods.

The income approach estimates value based on the expectation of future cash flows that a company will generate such as cash earnings, cost savings, tax deductions, and proceeds from disposition. These future cash flows are discounted to their present values using a discount rate derived from an analysis of the cost of capital of comparable publicly traded companies in our industry or similar lines of business as of each valuation date and is adjusted to reflect the risks inherent in our cash flows.

The market comparable approach estimates value based on a comparison of the Company to comparable public companies in a similar line of business. To determine our peer group of companies, we considered public enterprises with similar operations and selected those that are similar to our size, stage of life cycle, and financial leverage. From the comparable companies, a representative market value multiple is determined and applied to our results of operations to estimate the value of the Company.

Application of these approaches involved the use of estimates, judgments, and assumptions that are highly complex and subjective, such as those regarding our expected future cash flows, cost savings and expenses, discount rates, market multiples, the selection of comparable companies, and the probability of possible future events.

Emerging Growth Company:

Effective December 31, 2021, we ceased to be an emerging growth company and are now categorized as a Large Accelerated Filer based upon the current market capitalization of the Company according to Rule 12b-2 of the Exchange Act. As a result, we must comply with all financial disclosure and governance requirements applicable to Large Accelerated Filers.

Off-Balance Sheet Arrangements:

We do not have any off‑balance sheet arrangements, as defined by applicable SEC regulations.

Recent Accounting Pronouncements:

For information regarding recent accounting guidance and the impact of this guidance on our consolidated financial statements, see Note 2 to our consolidated financial statements included in Part II, Item 8 of this Annual Report on Form 10‑K.

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