#1|← | DocuSign Smarter, Easier, Trusted Agreements Q2 Fiscal 2024 paronadod and Tivt aucuaravayo are noncancelable and fees paid are non-refundable. * @rohe 1#2Safe Harbor 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, 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 "FY2024 Guidance" and "Q3 FY2024 Guidance in this presentation and any other statements about expected financial metrics, such as revenue, billings, non-GAAP gross margin, non-GAAP diluted weighted-average shares outstanding, and non-financial metrics, such as customer growth, as well as statements related to our expectations regarding our growth, and our intention to repurchase up to an additional $300 million of our common stock, including the expected timing, duration, volume and nature of such stock repurchase 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, rising and fluctuating interest rates, instability in the global banking sector, and market volatility on the global economy; our ability to estimate the size and growth of our total addressable market; our ability to compete effectively in an evolving and competitive market; the impact of any data breaches, cyberattacks or other malicious activity on our technology systems; our ability to effectively sustain and manage our growth and future expenses and achieve and maintain future profitability; our ability to attract new customers and maintain and expand our existing customer base; our ability to effectively implement and execute our restructuring plans; our ability to scale and update our platform to respond to customers' needs and rapid technological change; 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 or other indebtedness; 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 attract large organizations as users; 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 regional and global conflicts; our ability to successfully implement and maintain new and existing information technology systems, including our ERP system; 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, 2023 filed on March 27, 2023, our quarterly report on Form 10-Q for the quarter ended July 31, 2023, which we expect to file on September 7, 2023 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. DocuSign Public 2#3→ Non-GAAP Financial Measures and Other Key Metrics 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, amortization of debt discount and issuance costs, fair value adjustments to strategic investments, executive transition costs, lease-related impairment and lease-related charges, 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. 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 2023 and fiscal 2024, 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 is a key metric to measure our periodic performance. 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" below. DocuSign Public 3#4At a glance Market leadership World's #1 e-Signature solution Customer base 1.44M 1 Across all industries, segments, and geos Large market opportunity² ~$50BTAM Broader DocuSign opportunity (before and after signing) Q2 FY24³ performance $688M Revenue (26% Int'l) 11% Y/Y growth $711M Billings 10% Y/Y growth 25% Operating Margin (Non-GAAP) 102% Dollar Net Retention4 (1) As of July 31, 2023. (2) DocuSign estimate combining commissioned third-party research with internal customer count, pricing and spending data. (3) For the fiscal quarter ended July 31, 2023. (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., July 31, 2023), we first identify customers that were customers at the end of the prior year (e.g., July 31, 2022) 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. DocuSign Public 4#5Agreements are the foundation of doing business Sales Sales Contracts NDAS SOWS Service JELS Field Service Change Orders Work Agreements Marketing Vendor Agreements Sponsor Agreements Influencer Agreements DocuSign HR Offer Letters Background Checks Company Policies Procurement Vendor Contracts Purchase Orders Termination Letters Legal Amendments Affidavits SEC Filings DocuSign Public 5#6→ But agreement processes are manual & disconnected Business Process CRM Lead to Cash ERP Design to Operate ERP Procure to Pay HCM Hire to Retire AGREEMENT GAP Agreement Process Disconnected Manual Error-prone Time-consuming Not-sustainable DocuSign Public 6#7True transformation of the agreement process means going beyond the signature Agreement Generation + sert Document Fields Effective Date Party Address BIUA #. Design Pr Effective Address ID Verification DocuSign Your ID has been verified Review & Negotiation Comments BW How are these revisions? @Sam Shales ss This looks great, approved! KJ Okay, thanks team. Let's send it. Reply AGREEMENT PROCESS Signature Services Agreement ↓ /25/22 Cian S Automated Workflows !!! DocuSign CLM 8 F C Secure Repository 10 Documents Party is Fresh Software . In effect In effect. Status Employmen Techsphere Analytics Risk Analysis High High Medium Restrictive Covenants Most Favored Nations 1 IP Pre-Existing IP ■ Data Privacy & Protection Data Controller DocuSign Public 7#8↓ DocuSign unlocks the data that lives in agreements SLAS Products Status Sales Agreement * jeniful Obligations Important Terms Contract Risk DocuSign Public 8#9Redefining how the world comes together and agrees ↓ $ Smarter Personalized document generation Dynamic agreement Intelligent analytics and insights Easier Send and sign anytime, from practically anywhere Faster time to value, efficiency Extend with integrations and customization Trusted Highest level of assurance Support full range of functional areas/industries Superior security toolset, intelligent threat detection DocuSign Public 9#10→ Industry Leading Portfolio Lineup Across the Agreement Process eSignature The world's #1 way to sign electronically Editions range from personal to enterprise use Ecosystem Platform eSignature add-ons Enhanced options for any agreement scenario Add-ons include support for identity verification, web forms, monitor, payments, SMS delivery, notarization, API integrations and industry and country-specific capabilities CLM Top Rated Contract Lifecycle Management, for workflows before & after the signature Gen, CLM Essentials, CLM and CLM+ ISVS/Systems Integrators / Resellers/Developers 10 Repository/Search / Object Model / Al / API / Monitor/Admin Tools DocuSign Public 10