Biggest changeDocuSign, Inc.| 2024 Form 10-K | 55 Reconciliation of gross profit (loss) and gross margin: Year Ended January 31, (in thousands) 2024 2023 2022 GAAP gross profit $ 2,189,261 $ 1,979,827 $ 1,640,762 Add: Stock-based compensation 79,996 72,674 58,499 Add: Amortization of acquisition-related intangibles 8,857 9,613 11,670 Add: Employer payroll tax on employee stock transactions 2,262 2,184 7,524 Add: Lease-related impairment and lease-related charges 721 1,090 — Non-GAAP gross profit $ 2,281,097 $ 2,065,388 $ 1,718,455 GAAP gross margin 79 % 79 % 78 % Non-GAAP adjustments 4 % 3 % 4 % Non-GAAP gross margin 83 % 82 % 82 % GAAP subscription gross profit $ 2,226,803 $ 2,016,100 $ 1,693,611 Add: Stock-based compensation 51,660 46,916 31,152 Add: Amortization of acquisition-related intangibles 8,857 9,613 11,670 Add: Employer payroll tax on employee stock transactions 1,464 1,393 3,703 Add: Lease-related impairment and lease-related charges 505 447 — Non-GAAP subscription gross profit $ 2,289,289 $ 2,074,469 $ 1,740,136 GAAP subscription gross margin 83 % 83 % 83 % Non-GAAP adjustments 2 % 2 % 2 % Non-GAAP subscription gross margin 85 % 85 % 85 % GAAP professional services and other gross loss $ (37,542) $ (36,273) $ (52,849) Add: Stock-based compensation 28,336 25,758 27,347 Add: Employer payroll tax on employee stock transactions 798 791 3,821 Add: Lease-related impairment and lease-related charges 216 643 — Non-GAAP professional services and other gross loss $ (8,192) $ (9,081) $ (21,681) GAAP professional services and other gross margin (50) % (49) % (76) % Non-GAAP adjustments 39 % 37 % 45 % Non-GAAP professional services and other gross margin (11) % (12) % (31) % Reconciliation of income (loss) from operations and operating margin: Year Ended January 31, (in thousands) 2024 2023 2022 GAAP income (loss) from operations $ 31,634 $ (88,031) $ (61,884) Add: Stock-based compensation 611,835 533,100 408,542 Add: Amortization of acquisition-related intangibles 19,375 20,706 24,770 Add: Employer payroll tax on employee stock transactions 13,682 12,921 42,192 Add: Restructuring and other related charges 30,381 28,335 — Add: Lease-related impairment and lease-related charges 4,460 7,181 5,099 Add: Executive transition costs — 2,634 — Add: Acquisition-related expenses — — 387 Non-GAAP income from operations $ 711,367 $ 516,846 $ 419,106 GAAP operating margin 1 % (3) % (3) % Non-GAAP adjustments 25 % 24 % 23 % Non-GAAP operating margin 26 % 21 % 20 % DocuSign, Inc.| 2024 Form 10-K | 56 Reconciliation of net income (loss): Year Ended January 31, (in thousands, except per share data) 2024 2023 2022 GAAP net income (loss) $ 73,980 $ (97,454) $ (69,976) Add: Stock-based compensation 611,835 533,100 408,542 Add: Amortization of acquisition-related intangibles 19,375 20,706 24,770 Add: Employer payroll tax on employee stock transactions 13,682 12,921 42,192 Add: Amortization of debt discount and issuance costs 5,175 4,970 5,098 Add: Fair value adjustments to strategic investments 22 3,689 (5,270) Add: Restructuring and other related charges 30,381 28,335 — Add: Lease-related impairment and lease-related charges 4,460 7,181 5,099 Add: Executive transition costs — 2,634 — Add: Acquisition-related expenses — — 387 Add: Income Tax effect of non-GAAP adjustments (1) (136,023) (97,158) — Non-GAAP net income $ 622,887 $ 418,924 $ 410,842 (1) Represents the income tax adjustment using our estimated non-GAAP tax rate of 20%.
Biggest changeDocusign, Inc. | 2025 Form 10-K | 54 Reconciliation of gross profit (loss) and gross margin: Year Ended January 31, (in thousands) 2025 2024 2023 GAAP gross profit $ 2,355,080 $ 2,189,261 $ 1,979,827 Add: Stock-based compensation 76,987 79,996 72,674 Add: Amortization of acquisition-related intangibles 12,267 8,857 9,613 Add: Employer payroll tax on employee stock transactions 3,909 2,262 2,184 Add: Lease-related impairment and lease-related charges — 721 1,090 Non-GAAP gross profit $ 2,448,243 $ 2,281,097 $ 2,065,388 GAAP gross margin 79.1 % 79.3 % 78.7 % Non-GAAP adjustments 3.1 % 3.3 % 3.4 % Non-GAAP gross margin 82.2 % 82.6 % 82.1 % GAAP subscription gross profit $ 2,368,864 $ 2,226,803 $ 2,016,100 Add: Stock-based compensation 58,348 51,660 46,916 Add: Amortization of acquisition-related intangibles 12,267 8,857 9,613 Add: Employer payroll tax on employee stock transactions 2,882 1,464 1,393 Add: Lease-related impairment and lease-related charges — 505 447 Non-GAAP subscription gross profit $ 2,442,361 $ 2,289,289 $ 2,074,469 GAAP subscription gross margin 81.6 % 82.9 % 82.6 % Non-GAAP adjustments 2.6 % 2.3 % 2.3 % Non-GAAP subscription gross margin 84.2 % 85.2 % 84.9 % GAAP professional services and other gross loss $ (13,784) $ (37,542) $ (36,273) Add: Stock-based compensation 18,639 28,336 25,758 Add: Employer payroll tax on employee stock transactions 1,027 798 791 Add: Lease-related impairment and lease-related charges — 216 643 Non-GAAP professional services and other gross income (loss) $ 5,882 $ (8,192) $ (9,081) GAAP professional services and other gross margin (18.3) % (49.9) % (49.2) % Non-GAAP adjustments 26.1 % 39.0 % 36.9 % Non-GAAP professional services and other gross margin 7.8 % (10.9) % (12.3) % Docusign, Inc. | 2025 Form 10-K | 55 Reconciliation of income (loss) from operations and operating margin: Year Ended January 31, (in thousands) 2025 2024 2023 GAAP income (loss) from operations $ 199,928 $ 31,634 $ (88,031) Add: Stock-based compensation 605,499 611,835 533,100 Add: Amortization of acquisition-related intangibles 24,717 19,375 20,706 Add: Employer payroll tax on employee stock transactions 21,793 13,682 12,921 Add: Acquisition-related expenses 4,340 — — Add: Restructuring and other related charges 29,721 30,381 28,335 Add: Lease-related impairment and lease-related charges — 4,460 7,181 Add: Executive transition costs — — 2,634 Non-GAAP income from operations $ 885,998 $ 711,367 $ 516,846 GAAP operating margin 6.7 % 1.1 % (3.5) % Non-GAAP adjustments 23.1 % 24.7 % 24.0 % Non-GAAP operating margin 29.8 % 25.8 % 20.5 % Reconciliation of net income (loss): Year Ended January 31, (in thousands) 2025 2024 2023 GAAP net income (loss) $ 1,067,885 $ 73,980 $ (97,454) Add: Stock-based compensation 605,499 611,835 533,100 Add: Amortization of acquisition-related intangibles 24,717 19,375 20,706 Add: Employer payroll tax on employee stock transactions 21,793 13,682 12,921 Add: Acquisition-related expenses 4,340 — — Add: Restructuring and other related charges 29,721 30,381 28,335 Add: Amortization of debt discount and issuance costs — 5,175 4,970 Add: Fair value adjustments to strategic investments — 22 3,689 Add: Lease-related impairment and lease-related charges — 4,460 7,181 Add: Executive transition costs — — 2,634 Add: Income tax and other tax adjustments (1,006,746) (136,023) (97,158) Non-GAAP net income $ 747,209 $ 622,887 $ 418,924 Computation of free cash flow: Year Ended January 31, (in thousands) 2025 2024 2023 Net cash provided by operating activities $ 1,017,272 $ 979,526 $ 506,759 Less: Purchases of property and equipment (96,988) (92,391) (77,654) Non-GAAP free cash flow $ 920,284 $ 887,135 $ 429,105 Net cash provided by (used in) investing activities $ (312,876) $ 44,612 $ (191,197) Net cash used in financing activities $ (838,791) $ (946,039) $ (98,256) Docusign, Inc. | 2025 Form 10-K | 56 Computation of billings: Year Ended January 31, (in thousands) 2025 2024 2023 Revenue $ 2,976,739 $ 2,761,882 $ 2,515,915 Add: Contract liabilities and refund liability, end of period 1,479,266 1,343,792 1,191,269 Less: Contract liabilities and refund liability, beginning of period (1,343,792) (1,191,269) (1,049,106) Add: Contract assets and unbilled accounts receivable, beginning of period 20,189 16,615 18,273 Less: Contract assets and unbilled accounts receivable, end of period (17,825) (20,189) (16,615) Add: Contract assets and unbilled accounts receivable contributed by acquisitions 53 — — Less: Contract liabilities and refund liability contributed by acquisitions (5,071) — — Non-GAAP billings $ 3,109,559 $ 2,910,831 $ 2,659,736 Docusign, Inc. | 2025 Form 10-K | 57