Bringing Agreements to Life | DocuSign Q1 FY26 Performance

Bringing Agreements to Life | DocuSign Q1 FY26 Performance

• 1. Bringing Agreements to Life Q1 FY26

• 2. Safe Harbor 2 This presentation contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended, that are based on our management’s beliefs and assumptions and on information currently available to management, and which statements involve substantial risk and uncertainties. All statements contained in this presentation other than statements of historical fact, including statements regarding our future operating results and financial position, our business strategy and plans, market growth and trends, objectives for future operations, and the impact of such assumptions on our financial condition and results of operations are forward-looking statements. Forward-looking statements in this presentation also include, among other things, statements on pages titled “Guidance” and “Modeling Considerations” and any other statements about expected financial metrics, such as revenue, billings, free cash flow, non-GAAP gross margin, non-GAAP operating margin, non-GAAP operating expenses, and non-financial metrics, as well as statements related to our expectations regarding: the impact of foreign exchange rates; the timing and extent of customer renewals; the effectiveness of changes to our sales force and go-to-market strategy; the effects of seasonality; the timing and impact of our cloud migration transition; the benefits, the timing or rollout of future products and capabilities; customer demand and adoption of the Docusign Intelligent Agreement Management (“IAM”) platform; and our utilization of our stock repurchase program, including the expected timing, duration, volume and nature of share repurchase under such program. Forward-looking statements generally relate to future events or our future financial or operating performance. In some cases, you can identify forward-looking statements because they contain words such as “may,” “will,” “should,” “expects,” “plans,” “anticipates,” “could,” “intends,” “target,” “projects,” “contemplates,” “believes,”“estimates,” “predicts,” “potential,” or “continue” or the negative of these words or other similar terms or expressions that concern our expectations, strategy, plans or intentions. Forward-looking statements contained in this presentation include, but are not limited to, statements about: our expectations regarding global macro-economic conditions, including the effects of inflation, volatile interestrates or foreign exchange rates, and market volatility on the global economy; our inability to accurately estimate our market opportunity; our ability to compete effectively in an evolving and competitive market; the impact of any interruptions or delays in performance of our technical infrastructure, or data breaches, cyberattacks or other fraudulent or malicious activity attempting to exploit our technology systems, platform or brand name; our ability to effectively sustain and manage our growth and future expenses and maintain or increase profitability; our ability to attract new customers and retain and expand our existing customer base, including our ability to attract large organizations as users; our ability to scale and update our platform to respond to customers’ needs and rapid technological change, including our ability to successfully incorporate generative artificial intelligence into our existing and future products and to successfully deploy them; our ability to successfully develop, launch and sell IAM solutions; our ability to expand use cases within existing customers and vertical solutions; our ability to expand our operations and increase adoption of our platform internationally; our ability to strengthen and foster our relationships with developers; our ability to retain our direct sales force, customer success team and strategic partnerships around the world; our ability to identify targets for and execute potential acquisitions and to successfully integrate and realize the anticipated benefits of such acquisitions; our ability to maintain, protect and enhance our brand; the sufficiency of our cash, cash equivalents and capital resources to satisfy our liquidity needs; limitations on us due to obligations we have under our credit facility; our ability to realize the anticipated benefits of our stock repurchase program; our failure or the failure of our software to comply with applicable industry standards, laws and regulations; our ability to maintain, protect and enhance our intellectual property; our ability to successfully defend litigation against us; our ability to maintain our corporate culture; our ability to offer high-quality customer support; our ability to hire, retain and motivate qualified personnel, including executive level management; our ability to successfully manage and integrate executive management transitions; uncertainties regarding the impact of general economic and market conditions, including as a result of geopolitical conflict or changes in trade policies and practices; and our ability to maintain proper and effective internal controls. Additional risks and uncertainties that could affect our financial results are included in the sections titled “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” in our annual report on Form 10-K for the fiscal year ended January 31, 2025, filed on March 18, 2025, our quarterly report on Form 10-Q for the quarter ended April 30, 2025, which we expect to file on June 6, 2025 with the Securities and Exchange Commission (the “SEC”), and other filings that we make from time to time with the SEC. The forward-looking statements made in this presentation relate only to events as of the date on which such statements are made. We undertake no obligation to update any forward-looking statements after the date of this presentation or to conform such statements to actual results or revised expectations, except as required by law.

• 3. When evaluating the performance of our business and making operating plans, we do not consider these items (for example, when considering the impact of equity award grants, we place a greater emphasis on overall stockholder dilution rather than the accounting charges associated with such grants). We believe it is useful to exclude these expenses in order to better understand the long-term performance of our core business and to facilitate comparison of our results to those of peer companies and over multiple periods. In addition to these exclusions, we subtract an assumed provision for income taxes to calculate non-GAAP net income. We utilize a fixed long-term projected tax rate in our computation of the non-GAAP income tax provision to provide better consistency across the reporting periods. For fiscal 2025 and fiscal 2026, we have determined the projected non-GAAP tax rate to be 20%. Free cash flow: We define free cash flow as net cash provided by operating activities less purchases of property and equipment. We believe free cash flow is an important liquidity measure of the cash that is available (if any), after purchases of property and equipment, for operational expenses, investment in our business, and to make acquisitions. Free cash flow is useful to investors as a liquidity measure because it measures our ability to generate or use cash in excess of our capital investments in property and equipment. Once our business needs and obligations are met, cash can be used to maintain a strong balance sheet and invest in future growth. Billings: We define billings as total revenues plus the change in our contract liabilities and refund liability less contract assets and unbilled accounts receivable in a given period. Billings reflects sales to new customers plus subscription renewals and additional sales to existing customers. Only amounts invoiced to a customer in a given period are included in billings. We believe billings can be used to measure our periodic performance, when taking into consideration the timing aspects of customer renewals, which represents a large component of our business. Given that most of our customers pay in annual installments one year in advance, but we typically recognize a majority of the related revenue ratably over time, we use billings to measure and monitor our ability to provide our business with the working capital generated by upfront payments from our customers. For a reconciliation of these non-GAAP financial measures to the most directly comparable GAAP financial measure, please see “Reconciliation of GAAP to Non-GAAP Financial Measures” at the end of this presentation. To supplement our consolidated financial statements, which are prepared and presented in accordance with GAAP, we use certain non-GAAP financial measures, as described below, to understand and evaluate our core operating performance. These non-GAAP financial measures, which may be different than similarly-titled measures used by other companies, are presented to enhance investors’ overall understanding of our financial performance and should not be considered a substitute for, or superior to, the financial information prepared and presented in accordance with GAAP. We believe that these non-GAAP financial measures provide useful information about our financial performance, enhance the overall understanding of our past performance and future prospects, and allow for greater transparency with respect to important metrics used by our management for financial and operational decision-making. We present these non-GAAP measures to assist investors in seeing our financial performance using a management view, and because we believe that these measures provide an additional tool for investors to use in comparing our core financial performance over multiple periods with other companies in our industry. However, these non-GAAP measures are not intended to be considered in isolation from, a substitute for, or superior to our GAAP results. Non-GAAP gross profit, non-GAAP gross margin, non-GAAP operating expenses, non-GAAP income from operations, non-GAAP operating margin, non-GAAP net income and non-GAAP net income per share: We define these non-GAAP financial measures as the respective GAAP measures, excluding expenses related to stock-based compensation, employer payroll tax on employee stock transactions, amortization of acquisition-related intangibles, acquisition-related expenses, restructuring and other related charges, as these costs are not reflective of ongoing operations and, as applicable, other special items. The amount of employer payroll tax-related items on employee stock transactions is dependent on our stock price and other factors that are beyond our control and do not correlate to the operation of the business. Non-GAAP financial measures and other key metrics 3

• 4. At a glance 4 (1) As of April 30, 2025. (2) For the fiscal quarter ended April 30, 2025. (3) Please see Appendix slides for non-GAAP reconciliation. (4) FCF calculated as Operating Cash Flow less CapEx. Please see Appendix for calculation. Q1 FY262 performance $764M Total Revenue (28% Int’l) 8% Y/Y growth $740M Billings 4% Y/Y growth $228M Free Cash Flow 30% FCF Margin 29.5% Operating Margin (Non-GAAP) 3 Trusted, global brand1 World’s #1 e-Signature solution Unleashing the value of agreement data to power every company Our solution Intelligent Agreement Management Market leadership Ranked #1 “Most Trustworthy” software and telecommunications company in America in 2025 Over 1.7M customers and more than 1 billion users in over 180 markets across the globe Over 95% of Fortune 500 companies are Docusign customers 3 4

• 5. 5 Sales HR Service Marketing Legal Procurement Sales Contracts NDAs SOWs Field Service Change Orders Work Agreements Vendor Agreements Sponsor Agreements Influencer Agreements Offer Letters Background Checks Company Policies Vendor Contracts Purchase Orders Termination Letters Amendments Affidavits SEC Filings Agreements power business

• 6. 6 Source: Deloitte, May 2024; “Unlocking the Value of Agreement Management” 18% On average, companies spend an extra 18% of their time on agreements, resulting in over 55 billion hours wasted globally each year Sales Sales velocity slows, deals slip, and revenue is lost Procurement Value erodes as terms, SLAs, and obligations remain buried in flat files Legal Teams struggle to keep pace and lurking risks go unidentified HR Top talent is lost at the finish line to more nimble competitors The Agreement Trap destroys value for your business 6

• 7. Our Solution 7 Unleashing the value of agreement data to power every company

• 8. Create agreements in accessible, collaborative, & more automated ways to agreements & relationships on a trusted platform agreements seamlessly in ways that connect to your other systems Commit Manage 8

• 9. Docusign IAM Platform Transform the way you agree 9

• 10. 10 Investing in international growth 28% of Total revenue (Q1FY26)1 10% Y/Y Int’l revenue growth (Q1FY26)1 Market prioritization & investment Tier 1: Market leader Primary market focus for Direct GTM investment Fully localized digital experience Targeted investment in Resell partners Tier 2: Seed and grow High potential investment countries Seed with targeted direct investments, localized sales & support through partner and digital Tier 3: Digital & emerging Digital First strategy Indirect selling via key resellers (1) For the fiscal quarter ended April 30, 2025 compared to same period a year ago. Digital 180+ Countries Direct Focus 8

• 11. Accelerate value realization Drive ROI Fuel future growth Increase net retention Across all GTM teams Extend Partner integrations From single department to enterprise-wide Expand Signers From eSignature to Agreement Process Digital customer Receiving & signing documents Direct customer From digital to direct Paying web customer 11 Omni-channel experience throughout the customer journey

• 12. 12 How customers buy from us Prepaid Model (1) Rolling 4-quarter average through fiscal quarter ended April 30, 2025. Volume Capacity Pre-Set # of Envelopes Seat Based Contract per user Add-on Functionality Multiple levels of add-on functionality Dollar Weighted Average Contract Length1 Multi-Factor Subscription Model 39% >12 month duration 61% ≤12 month duration 19 MONTHS

• 13. 13 Docusign partner ecosystem Comprehensive network of cloud, service, and reseller partners Systems Integrators 500+ certified professionals across 10+ global & regional SIs ISVs (and 350+ more) Resellers 140+ resellers extend our reach, helping customers agree in 40+ countries

• 14. Financial Review 14

• 15. Y/Y Growth 9% 15 Total revenue growth 15% Web & Mobile (Digital) 85% Ent, Commercial & SMB (Direct) Revenue Contribution1 Direct v. Digital (1) Fiscal quarter ended April 30, 2025. 7% 7% 8% 8%

• 16. 16 Subscription revenue growth (1) Fiscal quarter ended April 30, 2025. 2% Professional Services & Other 98% Subscription Revenue Contribution1 Subscription v. Pro Serve and Other Y/Y Growth 8% 7% 8% 9% 8%

• 17. Y/Y Growth 17 Billings1 growth (1) Billings = total revenues plus the change in contract liabilities and refund liability less contract assets and unbilled accounts receivable in a given period. Please see Appendix for non-GAAP reconciliation. (2) Rolling 4-quarter year over year growth rate is used to smooth out the quarterly variability in the billings number. Rolling 4-Q Y/Y growth 2 5% 2% 9% 11% 4% 8% 6% 7% 7% 7%

• 18. 18 Healthy operating efficiency (1) Margins are as % of total revenue. Please see Appendix for non-GAAP reconciliation. (2) As of April 30, 2024 and 2025. Non-GAAP gross margin1 SUBSCRIPTION GROSS MARGIN TOTAL GROSS MARGIN Headcount2

• 19. 19 Operating expenses as a % of revenue (1) Please see Appendix slides for non-GAAP reconciliation. Non-GAAP S&M1 32.5% 30.4% 31.3% 31.9% 31.8% 12.3% 12.6% 12.8% 13.0% 13.1% 8.7% 7.0% 8.8% 8.6% 7.9% Non-GAAP R&D1 Non-GAAP G&A1

• 20. (1) Please see Appendix slides for non-GAAP reconciliation. (2) FCF calculated as Operating Cash Flow less CapEx. Please see Appendix for calculation. 20 Operating leverage and cash flow Non-GAAP Operating Income1 28.5% 32.2% 29.6% 28.8% 29.5% 36% 30% 31% 40% 33% 33% 27% 28% 36% 30% Operating Cash Flow1 Free Cash Flow2 % of total revenue

• 21. (1) Impact of foreign currency exchange rates on year-over-year guided revenue growth for the quarter ending July 31, 2025 is expected to be neutral. (2) Excluding the impact of foreign currency exchange rates on year-over-year guided growth, billings guidance range would be approximately 0.7% point lower for the quarter ending July 31, 2025. 21 Q2 FY26 guidance Q2 FY26 Total revenue1 $777M - $781M Subscription revenue $760M - $764M Billings2 $757M - $767M Non-GAAP gross margin 80.5% - 81.5% Non-GAAP operating margin 26.5% - 27.5% Non-GAAP diluted weightedaverage shares outstanding210M - 215M

• 22. 22 FY26 guidance FY26 Total revenue1 $3,151M - $3,163M Subscription revenue $3,083M - $3,095M Billings2 $3,285M - $3,339M Non-GAAP gross margin 80.7% - 81.7% Non-GAAP operating margin 27.8% - 28.8% Non-GAAP diluted weightedaverage shares outstanding210M - 215M (1) Impact of foreign currency exchange rates on year-over-year guided revenue growth for the fiscal year ending January 31, 2026 is expected to be neutral. (2) Excluding the impact of foreign currency exchange rates on year-over-year guided growth, billings guidance range would be approximately 0.7% point lower for the fiscal year ending January 31, 2026.

• 23. 23 Modeling considerations Topline Considerations: Foreign Exchange (F/X) Rates Growth Impact For both Q2 and Fiscal 2026, we expect a positive billings impact of approximately 0.7% year-over-year, and for revenue an approximately neutral year-over-year impact. This compares to the prior expected negative headwinds of approximately 1% year-over-year for billings and approximately 0.7% year-over-year for revenue in our prior Fiscal 2026 guidance issued in March of 2025. Seasonality Billings: For billings, we expect 2nd-half year-over-year growth to accelerate compared to 1st-half year-over-year growth, with Q4 growth expected to be stronger than Q3. This is due to the continued expected ramp in IAM deal volume and improvement in gross retention. Revenue: For revenue, we expect Q2 to represent slightly higher year-over-year growth versus 2nd half of Fiscal 2026, with recent digital and IAM strength being offset by a more conservative outlook given the economic environment. Dollar Net Retention Rate (DNR) We continue to expect DNR to moderately improve throughout the year based on both gross retention improvement and IAM upsell impact. IAM We continue to expect that IAM will represent a low double-digit percentage of the subscription book of business exiting Q4 of Fiscal 2026.

• 24. 24 Modeling considerations Profitability Considerations: Non-GAAP Gross Margin We continue to expect an approximate 1% point headwind due to the ongoing cloud migration for the full year Fiscal 2026. In Q1, gross margin was higher than forecasted due to higher revenue and a lower headwind due to slight shifts in the timing of migration efforts. For Q2, Q3, and Q4, we anticipate the headwind will be higher than the 1% indicated by full-year guidance. We continue to expect this migration impact to gradually ease in Fiscal 2027 and beyond. Non-GAAP Operating Margin Fiscal 2026 operating margin guidance is unchanged. We anticipate a 1.5% point headwind due to the 1% point cloud migration impact and 0.5% point annualized impact from Q2-specific comparison items explained in the prepared remarks. Additionally, we are not passing through the increase in revenue guidance to operating margin due to our updated foreign exchange rate forecast, which increases expenses for the remainder of Fiscal 2026. Q2 2026 guidance anticipates a year-over-year difference of approximately 5.2% points compared to Q2 2025 results. The majority of the difference between Q2 2026 and Q2 2025 can be attributed to the Q2-specific comparison items. The remainder of the increase is due to the timing of hiring, associated compensation changes, and depreciation expense from capitalized wages. Free Cash Flow (FCF) Margin We expect similar free cash flow seasonality in Fiscal 2026 compared to Fiscal 2025, with FCF margins lower in Q2 and Q3 before rebounding in Q4.

• 25. Appendix 25

• 26. Financial Metrics ($ in M) Q1FY25 Q2FY25 Q3FY25 Q4FY25 Q1FY26 Revenue $710 $736 $755 $776 $764 % Y/Y Change 7% 7% 8% 9% 8% Subscription Revenue $691 $717 $735 $758 $746 % Y/Y Change 8% 7% 8% 9% 8% International Revenue $197 $207 $212 $219 $217 % Y/Y Change 17% 15% 14% 12% 10% Billings $710 $725 $752 $923 $740 % Y/Y Change 5% 2% 9% 11% 4% Rolling 4-Qtr % Y/Y Change 1 8% 6% 7% 7% 7% Non-GAAP Operating Income $202 $237 $223 $224 $225 Non-GAAP Operating Margin (%) 28.5% 32.2% 29.6% 28.8% 29.5% Non-GAAP Free Cash Flow $232 $198 $211 $280 $228 Free Cash Flow Margin 33% 27% 28% 36% 30% Operational Metrics Q1FY25 Q2FY25 Q3FY25 Q4FY25 Q1FY26 Total Customers 1.56M 1.60M 1.63M 1.66M 1.71M % Y/Y Change 11% 11% 11% 10% 10% Enterprise & Commercial Customers2248k 253k 256k 260k 268k % Y/Y Change 13% 12% 10% 8% 8% Customers >$300k ACV31,059 1,066 1,075 1,131 1,123 % Y/Y Change -% 2% 2% 7% 6% Dollar Net Retention499% 99% 100% 101% 101% 26 (1) Rolling 4- quarter year over year growth rate is used to smooth out the quarterly variability in the billings number. (2) Comprised of customers who were not acquired through our Digital channel. (3) ACV = Annualized Contract Value (4) Compares the annual recurring revenue, or ARR, for active subscription contracts from Direct customers at two period end dates. To calculate our dollar-based net retention rate at the end of the base year (e.g., April 30, 2025), we first identify customers that were customers at the end of the prior year (e.g., April 30, 2024) and then divide the ARR attributed to those customers at the end of the base year by the ARR attributed to those same customers at the end of the prior year. The quotient obtained from this calculation is the dollar-based net retention rate. For clarity, we do not include customers serviced via our digital channel in this metric. Financial & operational metrics

• 27. 27 GAAP to Non-GAAP gross profit reconciliation Three Months Ended April 30, Gross Profit ($ in thousands) 2025 2024 GAAP gross profit 606,385 560,194 Add: Stock-based compensation 16,904 18,883 Add: Amortization of acquisition-related intangibles 3,565 2,070 Add: Employer payroll tax on employee stock transactions 1,873 1,023 Non-GAAP gross profit 628,727 582,170 GAAP gross margin 79.4% 78.9% Non-GAAP gross margin 82.3% 82.0% Three Months Ended April 30, Subscription Gross Profit ($ in thousands) 2025 2024 GAAP subscription revenue 746,202 691,483 Less: GAAP subscription cost of revenue 137,343 126,602 GAAP subscription gross profit 608,859 564,881 Add: Stock-based compensation 12,996 14,181 Add: Amortization of acquisition-related intangibles 3,565 2,070 Add: Employer payroll tax on employee stock transactions 1,445 792 Non-GAAP subscription gross profit 626,865 581,924 GAAP subscription gross margin 81.6% 81.7% Non-GAAP subscription gross margin 84.0% 84.2%

• 28. 28 GAAP to Non-GAAP operating income and free cash flow reconciliation Three Months Ended April 30, Operating Income ($ in thousands) 2025 2024 GAAP income from operations 60,255 22,628 Add: Stock-based compensation 145,596 137,876 Add: Amortization of acquisition-related intangibles 6,919 4,699 Add: Employer payroll tax on employee stock transactions 12,259 6,404 Add: Acquisition-related expenses — 1,358 Add: Restructuring and other related charges — 29,124 Non-GAAP income from operations 225,029 202,089 GAAP operating margin 7.9% 3.2% Non-GAAP operating margin 29.5% 28.5% Three Months Ended April 30, Free Cash Flow ($ in thousands) 2025 2024 Net cash provided by operating activities 251,439 254,826 Less: Purchases of property and equipment (23,624) (22,753) Non-GAAP free cash flow 227,815 232,073 Free cash flow margin 30% 33% Net cash used in investing activities (24,925) (60,777) Net cash used in financing activities (223,515) (169,874)

• 29. 29 GAAP to Non-GAAP operating expenses reconciliation Three Months Ended April 30, Sales & Marketing ($ in thousands) 2025 2024 GAAP sales and marketing 296,413 281,644 Less: Stock-based compensation (46,085) (46,271) Less: Amortization of acquisition-related intangibles (3,354) (2,629) Less: Employer payroll tax on employee stock transactions (3,940) (2,138) Non-GAAP sales and marketing 243,034 230,606 GAAP sales and marketing as a percentage of revenue 38.8% 39.7% Non-GAAP sales and marketing as a percentage of revenue 31.8% 32.5% Research & Development ($ in thousands) 2025 2024 GAAP research and development 159,447 134,320 Less: Stock-based compensation (54,431) (44,202) Less: Employer payroll tax on employee stock transactions (5,081) (2,565) Non-GAAP research and development 99,935 87,553 GAAP research and development as a percentage of revenue 20.9% 18.9% Non-GAAP research and development as a percentage of revenue 13.1% 12.3% General & Administrative ($ in thousands) 2025 2024 GAAP general and administrative 90,270 92,478 Less: Stock-based compensation (28,176) (28,520) Less: Employer payroll tax on employee stock transactions (1,365) (678) Less: Acquisition-related expenses — (1,358) Non-GAAP general and administrative 60,729 61,922 GAAP general and administrative as a percentage of revenue 11.8% 13.0% Non-GAAP general and administrative as a percentage of revenue 7.9% 8.7%

• 30. 30 Computation of billings Three Months Ended April 30, Computation of Billings ($ in thousands) 2025 2024 Revenue 763,654 709,640 Add: Contract liabilities and refund liability, end of period 1,450,718 1,340,680 Less: Contract liabilities and refund liability, beginning of period (1,479,266) (1,343,792) Add: Contract assets and unbilled accounts receivable, beginning of period 17,825 20,189 Less: Contract assets and unbilled accounts receivable, end of period (13,319) (17,179) Non-GAAP billings 739,612 709,538