Biggest changeDocuSign, Inc.| 2023 Form 10-K | 52 Reconciliation of gross profit (loss) and gross margin: Year Ended January 31, (in thousands) 2023 2022 2021 GAAP gross profit $ 1,979,827 $ 1,640,762 $ 1,088,989 Add: Stock-based compensation 72,674 58,499 42,658 Add: Amortization of acquisition-related intangibles 9,613 11,670 11,052 Add: Employer payroll tax on employee stock transactions 2,184 7,524 5,904 Add: Lease-related impairment and lease-related charges 1,090 — — Non-GAAP gross profit $ 2,065,388 $ 1,718,455 $ 1,148,603 GAAP gross margin 79 % 78 % 75 % Non-GAAP adjustments 3 % 4 % 4 % Non-GAAP gross margin 82 % 82 % 79 % GAAP subscription gross profit $ 2,016,100 $ 1,693,611 $ 1,121,405 Add: Stock-based compensation 46,916 31,152 20,793 Add: Amortization of acquisition-related intangibles 9,613 11,670 11,052 Add: Employer payroll tax on employee stock transactions 1,393 3,703 2,862 Add: Lease-related impairment and lease-related charges 447 — — Non-GAAP subscription gross profit $ 2,074,469 $ 1,740,136 $ 1,156,112 GAAP subscription gross margin 83 % 83 % 81 % Non-GAAP adjustments 2 % 2 % 3 % Non-GAAP subscription gross margin 85 % 85 % 84 % GAAP professional services and other gross loss $ (36,273) $ (52,849) $ (32,416) Add: Stock-based compensation 25,758 27,347 21,865 Add: Employer payroll tax on employee stock transactions 791 3,821 3,042 Add: Lease-related impairment and lease-related charges 643 — — Non-GAAP professional services and other gross loss $ (9,081) $ (21,681) $ (7,509) GAAP professional services and other gross margin (49) % (76) % (45) % Non-GAAP adjustments 37 % 45 % 35 % Non-GAAP professional services and other gross margin (12) % (31) % (10) % Reconciliation of income (loss) from operations and operating margin: Year Ended January 31, (in thousands) 2023 2022 2021 GAAP loss from operations $ (88,031) $ (61,884) $ (173,855) Add: Stock-based compensation 533,100 408,542 286,877 Add: Amortization of acquisition-related intangibles 20,706 24,770 25,618 Add: Employer payroll tax on employee stock transactions 12,921 42,192 34,042 Add: Acquisition-related expenses — 387 7,962 Add: Restructuring and other related charges 28,335 — — Add: Executive transition costs 2,634 — — Add: Lease-related impairment and lease-related charges 7,181 5,099 — Non-GAAP income from operations $ 516,846 $ 419,106 $ 180,644 GAAP operating margin (3) % (3) % (12) % Non-GAAP adjustments 24 % 23 % 24 % Non-GAAP operating margin 21 % 20 % 12 % DocuSign, Inc.| 2023 Form 10-K | 53 Reconciliation of net income (loss): Year Ended January 31, (in thousands, except per share data) 2023 2022 2021 GAAP net income (loss) $ (97,454) $ (69,976) $ (243,267) Add: Stock-based compensation 533,100 408,542 286,877 Add: Amortization of acquisition-related intangibles 20,706 24,770 25,618 Add: Employer payroll tax on employee stock transactions 12,921 42,192 34,042 Add: Acquisition-related expenses — 387 7,962 Add: Amortization of debt discount and issuance costs 4,970 5,098 28,001 Add: Loss on extinguishment of debt — — 33,752 Add: Tax expense related to intercompany IP transfer (1) — — 9,294 Add: Restructuring and other related charges 28,335 — — Add: Executive transition costs 2,634 — — Add: Lease-related impairment and lease-related charges 7,181 5,099 — Less: Fair value adjustments to strategic investments 3,689 (5,270) — Add: Income Tax effect of non-GAAP adjustments (2) (97,158) — — Non-GAAP net income $ 418,924 $ 410,842 $ 182,279 (1) Represents net change in tax liabilities related to an intercompany IP transfer (2) Represents the income tax adjustment using our estimated non-GAAP tax rate of 20%.
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%.
Our enterprise and commercial customers may start with just one use case and gradually implement additional use cases across their organization once they see the benefits of our software platform. Several of our largest enterprise customers have deployed our products for hundreds of use cases across their organizations.
Our enterprise and commercial customers may start with just one use case and gradually implement additional use cases across their organization once they see the benefits of our products. Several of our largest enterprise customers have deployed our software platform for hundreds of use cases across their organizations.
At that time, we would make adjustments to these potential future reserves when facts and circumstances change, such as the closing of a tax audit or the refinement of an estimate. Our estimate of the potential outcome of any uncertain tax position is subject to management's assessment of relevant risks, facts and circumstances existing at that time.
At that time, we would make adjustments to these potential future reserves when facts and circumstances change, such as the closing of a tax audit or when the refinement of an estimate is appropriate. Our estimate of the potential outcome of any uncertain tax position is subject to management's assessment of relevant risks, facts and circumstances existing at that time.
The period of benefit for commissions paid for the acquisition of the initial subscription contract is determined by considering our customer life and the technological life of our software platform and related significant features. The period of benefit for commissions on renewal subscription contracts is determined by considering the average contractual term for our renewal contracts.
The period of benefit for commissions paid for the acquisition of the initial subscription contract is determined by considering our customer life and the technological life of our software platform and related significant features. The period of benefit for commissions on renewal subscription contracts is determined by considering the weighted average contractual term for our renewal contracts.
Cash Flows from Financing Activities For the year ended January 31, 2023, cash used in financing activities of $98.3 million was primarily driven by $63.0 million used to repurchase 1.1 million shares of common stock at an average of $55.52 per share through our stock repurchase program which commenced in fiscal 2023, and $35.2 million payments for tax withholding on share settlements, net of proceeds associated with our equity plans.
For the year ended January 31, 2023, cash used in financing activities of $98.3 million was primarily driven by $63.0 million used to repurchase 1.1 million shares of common stock at an average of $55.52 per share through our stock repurchase program which commenced in fiscal 2023, and $35.2 million payments for tax withholding on share settlements, net of proceeds associated with our equity plans.
Cash Flows from Investing Activities For the year ended January 31, 2023, cash used in investing activities of $191.2 million was primarily driven by $109.8 million net purchases of marketable securities and $77.7 million purchases of property and equipment as we continued to invest in data center build outs to support our growing operations and capitalized software development projects.
For the year ended January 31, 2023, cash used in investing activities of $191.2 million was primarily driven by $109.8 million net purchases of marketable securities and $77.7 million purchases of property and equipment as we continued to invest in data center build outs to support our growing operations and capitalized software development projects.
Refer to Note 8 , Note 9 and Note 10 to the Consolidated Financial Statements in Part II, Item 8 of this Annual Report on Form 10-K for more information. We do not have any special purpose entities and we do not engage in off-balance sheet financing arrangements.
Refer to Not e 7 , Not e 8 and Note 9 to the Consolidated Financial Statements in Part II, Item 8 of this Annual Report on Form 10-K for more information. We do not have any special purpose entities and we do not engage in off-balance sheet financing arrangements.
We have experienced increased demand across multiple regions and are expanding our sales and marketing resources to capitalize on the potential growth of these markets. Additionally, we expect to continue to develop and enhance our strategic partnerships in key international markets as we grow internationally.
We have experienced increased demand across multiple regions and are focusing our sales and marketing resources to capitalize on the potential growth of these markets. Additionally, we expect to continue to develop and enhance our strategic partnerships in key international markets as we grow internationally.
We expect to continue to incur operating losses for the foreseeable future due to the investments we intend to make and may require additional capital resources to execute strategic initiatives to grow our business. We typically invoice our customers annually in advance.
We may continue to incur operating losses in the foreseeable future due to the investments we intend to make and may require additional capital resources to execute strategic initiatives to grow our business. We typically invoice our customers annually in advance.
We define commercial customers to include both mid-market companies, which includes companies outside the Global 2000 that have greater than 250 employees, and medium-sized businesses, or SMBs, which are companies with between 10 and 249 employees, in each case excluding any enterprise customers. We define VSBs as companies with fewer than 10 employees.
We define commercial customers to include both mid-market companies, which includes companies outside the Global 2000 that have greater than 250 employees, and medium-sized businesses (“SMBs”) which are companies with between 10 and 249 employees, in each case excluding any enterprise customers. We define VSBs as companies with fewer than 10 employees.
DocuSign, Inc.| 2023 Form 10-K | 49 Critical Accounting Policies and Estimates W e prepare our financial statements in accordance with generally accepted accounting principles (“GAAP”). Preparing these financial statements requires us to make estimates and assumptions that affect the reported amounts of assets, liabilities, revenue, expenses and related disclosures. We evaluate our estimates and assumptions on an ongoing basis.
DocuSign, Inc.| 2024 Form 10-K | 52 Critical Accounting Policies and Estimates W e prepare our financial statements in accordance with generally accepted accounting principles (“GAAP”). Preparing these financial statements requires us to make estimates and assumptions that affect the reported amounts of assets, liabilities, revenue, expenses and related disclosures. We evaluate our estimates and assumptions on an ongoing basis.
DocuSign, Inc.| 2023 Form 10-K | 50 We recognize compensation expense net of forfeitures that are estimated at the time of grant based on historical experience and our expectations regarding future pre-vesting termination behavior of employees and revise in subsequent periods if actual forfeitures differ from those estimates.
DocuSign, Inc.| 2024 Form 10-K | 53 We recognize compensation expense net of forfeitures that are estimated at the time of grant based on historical experience and our expectations regarding future pre-vesting termination behavior of employees and revise in subsequent periods if actual forfeitures differ from those estimates.
As of January 31, 2023, we had $1.0 billion in cash and cash equivalents and short-term investments. We also had $186.0 million in long-term investments that provide additional capital resources. We finance our operations primarily through payments by our customers for use of our product offerings and related services and through debt financing.
As of January 31, 2024, we had $1.0 billion in cash and cash equivalents and short-term investments. We also had $122.0 million in long-term investments that provide additional capital resources. We finance our operations primarily through payments by our customers for use of our product offerings and related services and through debt financing.
Sales and Marketing Expense Sales and marketing expense consists primarily of personnel costs, including sales commissions. These expenses also include expenditures related to advertising, marketing, promotional events and brand awareness activities, as well as allocated overhead costs. We expect sales and marketing expense to continue to increase in absolute dollars as we enhance our product offerings and implement marketing strategies.
These expenses also include expenditures related to advertising, marketing, promotional events and brand awareness activities, as well as allocated overhead costs. We expect sales and marketing expense to continue to increase in absolute dollars as we enhance our product offerings and implement marketing strategies. Research and Development Expense Research and development expense consists primarily of personnel costs.
DocuSign, Inc.| 2023 Form 10-K | 51 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.
DocuSign, Inc.| 2024 Form 10-K | 54 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.
We generally have standalone value for our professional services and recognize revenue based on standalone selling price as services are performed or upon completion of services for fixed fee contracts. Other revenue includes amounts derived from sales of on-premises solutions.
We price professional services on a time and materials basis and on a fixed fee basis. We generally have standalone value for our professional services and recognize revenue based on standalone selling price as services are performed or upon completion of services for fixed fee contracts. Other revenue includes amounts derived from sales of on-premises solutions.
We generate substantially all our revenue from sales of subscriptions, which accounted for 97%, 97% and 95% of our revenue in the years ended January 31, 2023, 2022 and 2021. Our subscription fees include the use of our products and access to customer support.
We generate substantially all our revenue from sales of subscriptions, which accounted for 97% of our revenue in each of the years ended January 31, 2024, 2023 and 2022. Our subscription fees include the use of our products and access to customer support.
Non-GAAP gross profit, non-GAAP gross margin, non-GAAP income from operations, non-GAAP operating margin and non-GAAP net income : 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, acquisition-related expenses, loss on extinguishment of debt, fair value adjustments to strategic investments, executive transition costs, lease-related impairment and lease-related charges, restructuring and other related charges, tax impact related to an intercompany IP transfer and, as applicable, other special items.
Non-GAAP gross profit, non-GAAP gross margin, non-GAAP income from operations, non-GAAP operating margin and non-GAAP net income : 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, acquisition-related expenses, fair value adjustments to strategic investments, executive transition costs, lease-related impairment and lease-related charges, restructuring and other related charges and, as applicable, other special items.
We believe that our sources of liquidity, including our cash, cash equivalents and investments, and expected future operating cash flows, and borrowing capacity available to us from our credit facility, are adequate to meet the potential cash commitments for the foreseeable future, including upcoming maturities in the next 12 months related to our 2023 Notes and 2024 Notes as well as other lease obligations.
We believe that our sources of liquidity, including our cash, cash equivalents and investments, and expected future operating cash flows, and borrowing capacity available to us from our credit facility, are adequate to meet the potential cash commitments for the foreseeable future, including upcoming maturities in the next 12 months related to our lease obligations.
We believe there is significant expansion opportunity with our customers following their initial adoption of our software platform. Increasing International Revenue Our international revenue represented 25%, 23% and 20% of our total revenue in each of the years ended January 31, 2023, 2022, and 2021, respectively.
We believe there is significant expansion opportunity with our customers following their initial adoption of our software platform. Increasing International Revenue Our international revenue represented 26%, 25% and 23% of our total revenue in each of the years ended January 31, 2024, 2023, and 2022.
For example, in Europe, we offer Standards-Based Signature (“SBS”) technology tailored for eIDAS. SBS supports signatures that involve digital certificates, including those specified in the EU’s eIDAS regulations for advanced and qualified electronic signatures.
For example, in Europe, we offer SBS technology tailored for the EU’s eIDAS regulations. SBS supports signatures that involve digital certificates, including those specified in the EU’s eIDAS regulations for advanced and qualified electronic signatures.
The increase was primarily due to the expansion of existing customers and the addition of new customers, as well as an increase in sales to our mid-market and enterprise customers through our direct and indirect go-to-market initiatives.
The increase was primarily due to the expansion of revenue from existing customers and the addition of new customers, as well as an increase in sales to our commercial and enterprise customers through our direct and indirect go-to-market initiatives.
In January 2021 we entered into a $500.0 million credit facility, which may be increased by an additional $250.0 million subject to customary terms and conditions. The credit facility is available for five years until January 11, 2026 to optimize our capital structure and strengthen our balance sheet.
In January 2021 we entered into a $500.0 million credit facility, as amended in May 2023, which may be increased by an additional $250.0 million subject to customary terms and conditions. The credit facility is available until January 11, 2026 to optimize our capital structure and strengthen our balance sheet.
While we generated positive cash flows from operations in the recent years, we have generated losses from operations in the past as reflected in our accumulated deficit of $1.6 billion as of January 31, 2023.
While we generated positive cash flows from operations in the recent years, we have generated losses from operations in the past as reflected in our accumulated deficit of $1.7 billion as of January 31, 2024.
DocuSign, Inc.| 2023 Form 10-K | 42 We believe there is a substantial opportunity for us to increase our international customer base by leveraging and expanding investments in our technology, direct sales force and strategic partnerships around the world, as well as helping existing U.S.-based customers manage agreements across their international businesses.
We believe there is a substantial opportunity for us to increase our international customer base by leveraging and expanding investments in our technology, direct sales force and strategic partnerships around the world, as well as helping existing U.S.-based customers manage agreements across their international businesses.
Further details of these transactions are described in Note 8 to the Consolidated Financial Statements, included in Part II, Item 8 of this Annual Report on Form 10-K. We were in compliance with all debt covenants at January 31, 2023.
Further details of these transactions are described in Not e 7 to the Consolidated Financial Statements, included in Part II, Item 8 of this Annual Report on Form 10-K. We were in compliance with all debt covenants at January 31, 2024.
There were no outstanding borrowings under the credit facility as of January 31, 2023. In September 2018, we issued and sold $575.0 million in aggregate principal amount of 0.5% Convertible Senior Notes due 2023 (the “2023 Notes”), of which $37.1 million remains unpaid as of January 31, 2023 .
There were no outstanding borrowings under the credit facility as of January 31, 2024. In September 2018, we issued and sold $575.0 million in aggregate principal amount of 0.5% Convertible Senior Notes due 2023 (the “2023 Notes”).
Estimating a non-GAAP tax rate of 20%, the income tax effect of non-GAAP adjustments was $79.7 million for the year ended January 31, 2022 and $32.9 million for the year ended January 31, 2021.
Estimating a non-GAAP tax rate of 20%, the income tax effect of non-GAAP adjustments was $79.7 million for the year ended January 31, 2022.
As of January 31, 2023, we had a total of over 1.3 million customers, including over 211,000 enterprise and commercial customers, compared to over 1.1 million customers and over 170,000 enterprise and commercial customers as of January 31, 2022. We define enterprise customers as companies generally included in the Global 2000.
As of January 31, 2024, we had a total of over 1.5 million customers, including approximately 242,000 enterprise and commercial customers, compared to over 1.3 million customers and approximately 211,000 enterprise and commercial customers as of January 31, 2023. We define enterprise customers as companies generally included in the Global 2000.
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 : 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.
Obligations and Commitments Our principal contractual obligations and commitments consist of obligations under the Notes (including principal and coupon interest), operating leases, as well as noncancelable contractual commitments that primarily relate to cloud infrastructure support and sales and marketing activities .
Obligations and Commitments Our principal contractual obligations and commitments consist of operating leases, as well as noncancelable contractual commitments that primarily relate to cloud infrastructure support and sales and marketing activities .
The number of our customers with greater than $300,000 in annualized contract value has increased from 852 customers as of January 31, 2022 to 1,080 customers as of January 31, 2023. Each of our customer types has a different purchasing pattern.
The number of our customers with greater than $300,000 in annualized contract value was 1,060 customers as of January 31, 2024 compared to 1,080 customers as of January 31, 2023. Each of our customer types has a different purchasing pattern.
Investing for Growth We believe that our market opportunity is large, and we plan to invest to support further growth. This includes optimizing our go-to-market efforts to focus on attractive growth opportunities and investing in research and development to drive product innovation and meet customer needs at scale. We also continue to assess and evaluate strategic acquisitions and investments.
This includes optimizing our go-to-market efforts to focus on attractive growth opportunities and investing in research and development to drive product innovation and meet customer needs at scale. We also continue to assess and evaluate strategic acquisitions and investments.
As we focus on infrastructure and technology that best serve our customers across industries, we will prioritize initiatives that accelerate our product capabilities. We believe these collective activities will lead to continued expansion within our current customers’ organizations and attract new customers.
As we focus on infrastructure and technology that best serve our customers across industries, we will prioritize initiatives that accelerate our product capabilities and expand our product solutions. We believe these collective activities will help us retain and expand within our current customers’ organizations and attract new customers.
In January 2021, we issued and sol d $690.0 million in aggregate principal amount of 0% Convertible Senior Notes due 2024 (the “2024 Notes”).
In January 2021, we issued and sol d $690.0 million in aggregate principal amount of 0% Convertible Senior Notes due 2024 (the “2024 Notes”). We fully settled the outstanding principal of the 2023 Notes and 2024 Notes and during the year ended January 31, 2024.
Subscriptions generally range from one to three years, and substantially all our multi-year customers pay in annual installments, one year in advance. We also generate revenue from professional and other non-subscription services, which consists primarily of fees associated with providing new customers deployment and integration services. Other revenue includes amounts derived from sales of on-premises solutions.
Subscriptions generally range from one to three years, and substantially all our multi-year customers pay in annual installments, one year in advance. DocuSign, Inc.| 2024 Form 10-K | 43 We also generate revenue from professional and other non-subscription services, which consists primarily of fees associated with providing new customers deployment and integration services.
Components of Results of Operations Revenue We derive revenue primarily from the sale of subscriptions and, to a lesser extent, professional services. Subscription Revenue Subscription revenue consists of fees for the use of our software platform and our technical infrastructure and access to customer support, which includes phone or email support. We typically invoice customers annually in advance.
DocuSign, Inc.| 2024 Form 10-K | 45 Components of Results of Operations Revenue We derive revenue primarily from the sale of subscriptions and, to a lesser extent, professional services. Subscription Revenue Subscription revenue consists of fees for the use of our software platform and our technical infrastructure and access to customer support, which includes phone or email support.
We recognize subscription revenue ratably over the term of the contract subscription period beginning on the date access to our software platform is provided. Professional Services and Other Revenue Professional services revenue includes fees associated with new customers requesting deployment and integration services. We price professional services on a time and materials basis and on a fixed fee basis.
We typically invoice customers annually in advance. We recognize subscription revenue ratably over the term of the contract subscription period beginning on the date access to our software platform is provided. Professional Services and Other Revenue Professional services revenue includes fees associated with new customers requesting deployment and integration services.
Operating Expenses Our operating expenses consist of sales and marketing, research and development and general and administrative expenses. As our revenues continue to increase, our operating expenses as a percentage of revenue may increase or decrease at different rates, driven by the timing of revenue recognition, the timing of hiring, our investments in growth and other factors.
As our revenues continue to increase, our operating expenses as a percentage of revenue may increase or decrease at different rates, driven by the timing of revenue recognition, the timing of hiring, our investments in growth and other factors. Sales and Marketing Expense Sales and marketing expense consists primarily of personnel costs, including sales commissions.
Research and Development Expense Research and development expense consists primarily of personnel costs. These expenses also include non-personnel costs, such as subcontracting, consulting and professional fees for third-party development resources, as well as allocated overhead costs. Our research and development efforts focus on maintaining and enhancing existing functionality and adding new functionality.
These expenses also include non-personnel costs, such as subcontracting, consulting and professional fees for third-party development resources, as well as allocated overhead costs. Our research and development efforts focus on maintaining and enhancing existing functionality and adding new functionality. We expect research and development expense to increase in absolute dollars as we invest in the enhancement of our software platform.
Cost of Professional Services and Other Revenue Cost of professional services and other revenue consists primarily of personnel costs for our professional services delivery team, travel-related costs and allocated overhead costs. DocuSign, Inc.| 2023 Form 10-K | 43 Gross Profit and Gross Margin Gross profit is total revenue less total cost of revenue.
Cost of Professional Services and Other Revenue Cost of professional services and other revenue consists primarily of personnel costs for our professional services delivery team, travel-related costs and allocated overhead costs. Gross Profit and Gross Margin Gross profit is total revenue less total cost of revenue. Gross margin is gross profit expressed as a percentage of total revenue.
DocuSign, Inc.| 2023 Form 10-K | 48 Cash Flows The following table summarizes our cash flows for the periods indicated: Year Ended January 31, (in thousands) 2023 2022 Net cash provided by (used in): Operating activities $ 506,759 $ 506,467 Investing activities (191,197) (162,909) Financing activities (98,256) (394,621) Effect of foreign exchange on cash, cash equivalents and restricted cash (3,784) (5,594) Net change in cash, cash equivalents and restricted cash $ 213,522 $ (56,657) Cash Flows from Operating Activities Cash provided by operating activities increased to $506.8 million for the year ended January 31, 2023 from $506.5 million for the year ended January 31, 2022.
DocuSign, Inc.| 2024 Form 10-K | 51 Cash Flows The following table summarizes our cash flows for the periods indicated: Year Ended January 31, (in thousands) 2024 2023 Net cash provided by (used in): Operating activities $ 979,526 $ 506,759 Investing activities 44,612 (191,197) Financing activities (946,039) (98,256) Effect of foreign exchange on cash, cash equivalents and restricted cash 199 (3,784) Net change in cash, cash equivalents and restricted cash $ 78,298 $ 213,522 Cash Flows from Operating Activities Cash provided by operating activities was $979.5 million for the year ended January 31, 2024.
Executive Overview of Fiscal 2023 Results Overview DocuSign is the global leader in the eSignature category. We offer products that address broader agreement workflows and digital transformation, enabling agreements to be signed electronically on a wide variety of devices, from virtually anywhere in the world, securely.
Executive Overview of Fiscal 2024 Results Overview DocuSign offers products that address agreement workflows and digital transformation as part of its agreement management platform, enabling agreements to be signed electronically on a wide variety of devices, from virtually anywhere in the world, securely.
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, we 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 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%.
Sales and Marketing Year Ended January 31, 2023 vs 2022 (in thousands) 2023 2022 Sales and marketing $ 1,242,711 $ 1,076,527 15 % Percentage of revenue 49 % 51 % Sales and marketing expenses decreased as a percentage of revenue due to savings on personnel costs from the restructuring plan implemented during the third quarter of fiscal 2023 and shifts in the allocation of resources for our go-to-market initiatives.
Sales and Marketing Year Ended January 31, 2024 vs 2023 (in thousands) 2024 2023 Sales and marketing $ 1,168,137 $ 1,242,711 (6) % Percentage of revenue 42 % 49 % Sales and marketing expenses decreased $74.6 million, or 6%, in the year ended January 31, 2024, primarily driven by savings on personnel costs from the restructuring plans implemented during the third quarter of fiscal 2023 and the first quarter of fiscal 2024 as well as shifts in the allocation of resources for our go-to-market initiatives.
Computation of free cash flow: Year Ended January 31, (in thousands) 2023 2022 2021 Net cash provided by operating activities $ 506,759 $ 506,467 $ 296,954 Less: Purchases of property and equipment (77,654) (61,396) (82,395) Non-GAAP free cash flow $ 429,105 $ 445,071 $ 214,559 Net cash (used in) provided by investing activities $ (191,197) $ (162,909) $ 81,229 Net cash used in financing activities $ (98,256) $ (394,621) $ (58,976) Computation of billings: Year Ended January 31, (in thousands) 2023 2022 2021 Revenue $ 2,515,915 $ 2,107,213 $ 1,453,047 Add: Contract liabilities and refund liability, end of period 1,191,269 1,049,106 800,940 Less: Contract liabilities and refund liability, beginning of period (1,049,106) (800,940) (522,201) Add: Contract assets and unbilled accounts receivable, beginning of period 18,273 21,021 15,082 Less: Contract assets and unbilled accounts receivable, end of period (16,615) (18,273) (21,021) Add: Contract assets and unbilled accounts receivable contributed by acquisitions — — 6,589 Less: Contract liabilities and refund liability contributed by acquisitions — — (9,344) Non-GAAP billings $ 2,659,736 $ 2,358,127 $ 1,723,092 DocuSign, Inc.| 2023 Form 10-K | 54
Computation of free cash flow: Year Ended January 31, (in thousands) 2024 2023 2022 Net cash provided by operating activities $ 979,526 $ 506,759 $ 506,467 Less: Purchases of property and equipment (92,391) (77,654) (61,396) Non-GAAP free cash flow $ 887,135 $ 429,105 $ 445,071 Net cash provided by (used in) investing activities $ 44,612 $ (191,197) $ (162,909) Net cash used in financing activities $ (946,039) $ (98,256) $ (394,621) Computation of billings: Year Ended January 31, (in thousands) 2024 2023 2022 Revenue $ 2,761,882 $ 2,515,915 $ 2,107,213 Add: Contract liabilities and refund liability, end of period 1,343,792 1,191,269 1,049,106 Less: Contract liabilities and refund liability, beginning of period (1,191,269) (1,049,106) (800,940) Add: Contract assets and unbilled accounts receivable, beginning of period 16,615 18,273 21,021 Less: Contract assets and unbilled accounts receivable, end of period (20,189) (16,615) (18,273) Non-GAAP billings $ 2,910,831 $ 2,659,736 $ 2,358,127 DocuSign, Inc.| 2024 Form 10-K | 57
Periodically, we evaluate these factors and review whether events or changes in circumstances have occurred that could impact the period of benefit. Any future changes in circumstances around our customer life and average contractual terms of renewal contracts may materially change the periods of benefit and therefore the amortization amounts recognized in our consolidated statement of operations and comprehensive loss.
Any future changes in circumstances around our customer life and weighted average contractual terms of renewal contracts may materially change the periods of benefit and therefore the amortization amounts recognized in our consolidated statement of operations and comprehensive income (loss).
DocuSign, Inc.| 2023 Form 10-K | 45 Cost of Revenue and Gross Margin Year Ended January 31, 2023 vs 2022 (in thousands) 2023 2022 Cost of revenue: Subscription $ 426,077 $ 343,661 24 % Professional services and other 110,011 122,790 (10) % Total cost of revenue $ 536,088 $ 466,451 15 % Gross margin: Subscription 83 % 83 % — pts Professional services and other (49) % (76) % 27 pts Total gross margin 79 % 78 % 1 pts Cost of subscription revenue increased $82.4 million, or 24% in the year ended January 31, 2023, primarily driven by higher costs to support our growing customer base.
DocuSign, Inc.| 2024 Form 10-K | 48 Cost of Revenue and Gross Margin Year Ended January 31, 2024 vs 2023 (in thousands) 2024 2023 Cost of revenue: Subscription $ 459,905 $ 426,077 8 % Professional services and other 112,716 110,011 2 % Total cost of revenue $ 572,621 $ 536,088 7 % Gross margin: Subscription 83 % 83 % — pts Professional services and other (50) % (49) % (1) pts Total gross margin 79 % 79 % — pts Cost of subscription revenue increased $33.8 million, or 8%, in the year ended January 31, 2024, primarily driven by higher costs to support our growing customer base.
Cash provided by operating activities is primarily driven by the timing of customer collections. In the year ended January 31, 2023, we experienced a decrease in amounts billed to customers and recognized as contract liabilities, partially offset by increased collections of accounts receivable.
Cash provided by operating activities was $506.8 million for the year ended January 31, 2023. Cash provided by operating activities increased slightly due to increases in collections of accounts receivable and higher revenues, partially offset by a decrease in amounts billed to customers and recognized as contract liabilities.
We continue to invest in a variety of customer programs and initiatives, which, along with expanded customer use cases, have helped increase our subscription revenue over time. We expect subscription revenue to continue to increase as existing customers increase their usage across their organizations while we offer new functionality, develop new products and attract new customers.
We continue to invest in a variety of customer programs and initiatives, which, along with expanded customer use cases, have helped increase our subscription revenue over time.
DocuSign, Inc.| 2023 Form 10-K | 44 Discussion of Results of Operations The following table summarizes our historical consolidated statements of operations data: Year Ended January 31, (in thousands) 2023 As % of Revenue 2022 As % of Revenue Revenue: Subscription $ 2,442,177 97 % $ 2,037,272 97 % Professional services and other 73,738 3 69,941 3 Total revenue 2,515,915 100 2,107,213 100 Cost of revenue: Subscription 426,077 17 343,661 16 Professional services and other 110,011 4 122,790 6 Total cost of revenue 536,088 21 466,451 22 Gross profit 1,979,827 79 1,640,762 78 Operating expenses: Sales and marketing 1,242,711 49 1,076,527 51 Research and development 480,584 19 393,362 19 General and administrative 316,228 13 232,757 11 Restructuring and other related charges 28,335 1 — — Total operating expenses 2,067,858 82 1,702,646 81 Loss from operations (88,031) (3) (61,884) (3) Interest expense (6,389) (1) (6,443) — Interest income and other income, net 4,539 — 1,413 — Loss before provision for income taxes (89,881) (4) (66,914) (3) Provision for income taxes 7,573 — 3,062 — Net loss $ (97,454) (4) % $ (69,976) (3) % For a comparison of our results of operations for the fiscal years ended January 31, 2022 and 2021, see Item 7, Management’s Discussion and Analysis of Financial Condition and Results of Operations, of our Annual Report on Form 10-K for the fiscal year ended January 31, 2022, filed with the SEC on March 25, 2022.
DocuSign, Inc.| 2024 Form 10-K | 47 Discussion of Results of Operations The following table summarizes our historical consolidated statements of operations data: Year Ended January 31, (in thousands) 2024 As % of Revenue 2023 As % of Revenue Revenue: Subscription $ 2,686,708 97 % $ 2,442,177 97 % Professional services and other 75,174 3 73,738 3 Total revenue 2,761,882 100 2,515,915 100 Cost of revenue: Subscription 459,905 17 426,077 17 Professional services and other 112,716 4 110,011 4 Total cost of revenue 572,621 21 536,088 21 Gross profit 2,189,261 79 1,979,827 79 Operating expenses: Sales and marketing 1,168,137 42 1,242,711 49 Research and development 539,488 20 480,584 19 General and administrative 419,621 15 316,228 13 Restructuring and other related charges 30,381 1 28,335 1 Total operating expenses 2,157,627 78 2,067,858 82 Income (loss) from operations 31,634 1 (88,031) (3) Interest expense (6,844) — (6,389) (1) Interest income and other income, net 68,889 2 4,539 — Income (loss) before provision for income taxes 93,679 3 (89,881) (4) Provision for income taxes 19,699 — 7,573 — Net income (loss) $ 73,980 3 % $ (97,454) (4) % For a comparison of our results of operations for the fiscal years ended January 31, 2023 and 2022, see Item 7, Management’s Discussion and Analysis of Financial Condition and Results of Operations, of our Annual Report on Form 10-K for the fiscal year ended January 31, 2023, filed with the SEC on March 27, 2023.
Professional services and other revenue accounted for the remainder of total revenue. We anticipate continuing to invest in customer success through our professional services offerings as we believe it plays an important role in accelerating our customers’ adoption of our products, which helps drive customer retention and expansion.
We anticipate continuing to invest in customer success through our professional services offerings as we believe it plays an important role in accelerating our customers’ adoption of our products, which helps drive customer retention and expansion. We offer subscriptions to our products to businesses at all scales, from global enterprise down to local, VSBs.
Revenue Year Ended January 31, 2023 vs 2022 (in thousands) 2023 As % of Revenue 2022 As % of Revenue Revenue: Subscription $ 2,442,177 97 % $ 2,037,272 97 % 20 % Professional services and other 73,738 3 69,941 3 5 % Total revenue $ 2,515,915 100 % $ 2,107,213 100 % 19 % Subscription revenue increased $404.9 million, or 20%, in the year ended January 31, 2023.
Revenue Year Ended January 31, 2024 vs 2023 (in thousands) 2024 As % of Revenue 2023 As % of Revenue Revenue: Subscription $ 2,686,708 97 % $ 2,442,177 97 % 10 % Professional services and other 75,174 3 73,738 3 2 % Total revenue $ 2,761,882 100 % $ 2,515,915 100 % 10 % Subscription revenue increased $244.5 million, or 10%, in the year ended January 31, 2024.
VSBs tend to become customers quickly with very little to no direct sales or customer support interaction and generate smaller average contract values, while commercial and enterprise customers typically involve longer sales cycles, larger contract values and greater expansion opportunities for us.
VSBs typically become customers by quickly utilizing our digital and self-serve channels and generate smaller average contract values, while commercial and enterprise customers typically involve longer sales cycles, larger contract values and greater expansion opportunities for us.
Restructuring and Other Related Charges Restructuring and other related charges consist primarily of costs associated with restructuring plans approved by our Board of Directors.
We expect general and administrative expense to increase in absolute dollars to support the overall growth of our operations. Restructuring and Other Related Charges Restructuring and other related charges consist primarily of costs associated with restructuring plans approved by our board of directors.
DocuSign, Inc.| 2023 Form 10-K | 46 Research and Development Year Ended January 31, 2023 vs 2022 (in thousands) 2023 2022 Research and development $ 480,584 $ 393,362 22 % Percentage of revenue 19 % 19 % Research and development expenses increased $87.2 million, or 22%, in the year ended January 31, 2023, primarily due to investments in workforce and technology support to accommodate growth.
Research and Development Year Ended January 31, 2024 vs 2023 (in thousands) 2024 2023 Research and development $ 539,488 $ 480,584 12 % Percentage of revenue 20 % 19 % Research and development expenses increased $58.9 million, or 12%, in the year ended January 31, 2024, primarily due to investments in our workforce and product innovation.
General and Administrative Year Ended January 31, 2023 vs 2022 (in thousands) 2023 2022 General and administrative $ 316,228 $ 232,757 36 % Percentage of revenue 13 % 11 % General and administrative expenses increased $83.5 million, or 36%, in the year ended January 31, 2023, primarily due to investments in workforce and technology support to accommodate the operations and growth in our business.
DocuSign, Inc.| 2024 Form 10-K | 49 General and Administrative Year Ended January 31, 2024 vs 2023 (in thousands) 2024 2023 General and administrative $ 419,621 $ 316,228 33 % Percentage of revenue 15 % 13 % General and administrative expenses increased $103.4 million, or 33%, in the year ended January 31, 2024, primarily due to investments in workforce and information technology.
DocuSign, Inc.| 2023 Form 10-K | 41 Financial Results for the Year Ended January 31, 2023 (in thousands) Year Ended January 31, 2023 Total revenue $ 2,515,915 Total costs and expenses 2,603,946 Total stock-based compensation expense 538,726 Loss from operations (88,031) Net loss (97,454) Cash provided by operating activities 506,759 Capital expenditures (77,654) Cash, cash equivalents, restricted cash and investments were $1.2 billion as of January 31, 2023.
Financial Results for the Year Ended January 31, 2024 (in thousands) Year Ended January 31, 2024 Total revenue $ 2,761,882 Total costs and expenses 2,730,248 Total stock-based compensation expense 616,847 Income from operations 31,634 Net income 73,980 Cash provided by operating activities 979,526 Capital expenditures (92,391) Cash, cash equivalents, restricted cash and investments were $1.2 billion as of January 31, 2024.
DocuSign’s product offerings, including DocuSign eSignature, allow organizations to do business faster with less risk and lower costs, while providing better experiences for customers and employees. As a result, over 1.3 million customers and more than a billion users worldwide utilize DocuSign products to create, upload and send documents for multiple parties to sign electronically.
DocuSign’s core product offerings, including the world’s leading electronic signature product, allow organizations to do business faster with less risk and at a lower cost, while providing a better experience for customers. As a result, over 1.5 million customers and more than a billion users worldwide utilize our platform to accelerate and simplify the process of doing business.
We expect research and development expense to increase in absolute dollars as we invest in the enhancement of our software platform. General and Administrative Expense General and administrative expense consists primarily of employee-related costs for those employees providing administrative services such as legal, human resources, information technology related to internal systems, accounting and finance.
General and Administrative Expense General and administrative expense consists primarily of employee-related costs for those employees providing administrative services such as legal, human resources, information technology related to internal systems, accounting and finance. These expenses also include certain third-party consulting services, certain facilities costs, allocated overhead costs and lease-related charges.
Significant increases consisted of: • $41.4 million in stock-based compensation expense and $31.4 million in personnel costs due to higher average headcount and annual salary increases; and • $10.4 million due to higher information technology costs.
Increases primarily consisted of: • $34.2 million in stock-based compensation expense and $15.1 million in personnel costs due to annual merit increases; and • $11.9 million due to higher information technology costs to drive product innovation.
Key Factors Affecting Our Performance We believe that our future performance will depend on many factors, including the following: Growing Customer Base We are highly focused on continuing to acquire new customers to support our long-term growth.
Key Factors Affecting Our Performance We believe that our future performance will depend on many factors, including the following: Investing for Growth We believe that our market opportunity is large, and we plan to invest to support further growth.
Interest Expense and Loss on Extinguishment of Debt Interest expense consists primarily of contractual interest expense, amortization of discount and amortization of debt issuance costs on our Notes. The loss on extinguishment of debt consists of the difference between the fair value and the net carrying value of our Notes at settlement.
Interest Expense Interest expense consists primarily of contractual interest expense and amortization of debt issuance costs on our Convertible Senior Notes due 2023 and our Convertible Senior Notes due 2024 (collectively, the “Notes”).
We have invested, and expect to continue to invest in our go-to-market efforts involving a combination of direct sales, partner-assisted sales and digital self-service purchasing.
DocuSign, Inc.| 2024 Form 10-K | 44 Growing Customer Base We are highly focused on continuing to acquire new customers to support our long-term growth. We have invested, and expect to continue to invest in our go-to-market efforts involving an omnichannel approach that consists of direct sales, partner-assisted sales and digital self-service purchasing.
Provision for Income Taxes Our provision for income taxes consists primarily of income taxes in certain foreign jurisdictions where we conduct business, and tax benefits arising from deductions for stock-based compensation. We have a valuation allowance against our U.S. consolidated group and certain foreign deferred tax assets.
Provision for Income Taxes Our provision for income taxes consists primarily of income taxes in certain foreign jurisdictions where we conduct business and U.S. income taxes from a tax law change related to mandatory capitalization of research and development expenses for tax years starting January 1, 2022.
For the year ended January 31, 2022, cash provided by investing activities of $162.9 million was primarily driven by $93.4 million net purchases of marketable securities and $61.4 million purchases of property and equipment as we continued to invest in data center build outs to support our growing operations and capitalized software development projects.
The increase was partially offset by purchases of property and equipment of $92.4 million as we continue to support operations at our data centers and invest in capitalized software development projects.
There were no restructuring and other related charges in the year ended January 31, 2022. DocuSign, Inc.| 2023 Form 10-K | 47 Liquidity and Capital Resources Our principal sources of liquidity were cash, cash equivalents and investments as well as cash generated from operations.
The increase in the provision for income taxes in the current year is a result of higher pre-tax income and limitations on net operating losses allowed to reduce taxable income. DocuSign, Inc.| 2024 Form 10-K | 50 Liquidity and Capital Resources Our principal sources of liquidity were cash, cash equivalents and investments as well as cash generated from operations.
We offer more than 400 off-the-shelf, prebuilt integrations with the applications that many of our customers already use—including those offered by Google, Microsoft, Oracle, Salesforce, SAP, and ServiceNow—so that they can create, sign, send and manage agreements from directly within these applications.
We have an omnichannel go-to-market approach that consists of direct sales, partners to sell to our customers, and digital self-serve. We offer more than 900 active partner integrations with the applications that many of our customers already use so that they can create, commit, and manage agreements directly within these applications.
For the year ended January 31, 2022, cash used in financing activities of $394.6 million was primarily driven by $316.7 million payments for tax withholding on share settlements, net of proceeds associated with our equity plans. We also used $77.9 million for repayments of our 2023 Notes.
Cash Flows from Financing Activities For the year ended January 31, 2024, cash used in financing activities of $946.0 million was primarily driven by the maturity of the Notes, stock repurchase program, and payments related to our equity plans. We fully repaid the 2023 Notes and 2024 Notes during fiscal 2024 for $727.0 million.
Significant increases consisted of: • $29.2 million in personnel costs and $15.8 million in stock-based compensation expense primarily due to higher average headcount and annual salary increases; • $20.8 million in operating costs to support our platform and the growth in our revenue, including a $13.7 million increase in hosting costs and an $8.8 million increase in subscription reseller fees; • $10.1 million due to higher information technology costs; and • $5.7 million in depreciation and amortization, which reflects the impact of higher data center costs and capitalized software assets.
Increases primarily consisted of: • $13.3 million in operating costs to support our platform and revenue growth, including increases in hosting costs as well as processing and authentication costs; • $7.1 million due to higher information technology costs; and • $6.9 million in depreciation on our capitalized software projects.
Significant increases consisted of: • $33.4 million in stock-based compensation expense and $17.6 million in personnel costs due to higher average headcount and annual salary increases; • $23.4 million in professional fees due to increases in consultant fees to support the implementation of a new enterprise resource planning system, and legal and other fees; and • $7.8 million due to higher information technology costs.
Increases primarily consisted of: • $55.6 million in stock-based compensation expense driven by charges due to executive new hire grants and transitions and annual merit increases; • $27.8 million in personnel costs driven by annual salary increases to align with the increasing cost of labor; and • $11.4 million due to higher information technology costs.
We expect to maintain this valuation allowance for the foreseeable future or until it becomes more likely than not that the benefit of these U.S. and foreign deferred tax assets will be realized by way of expected future taxable income.
We have a valuation allowance against our U.S. consolidated group and certain foreign deferred tax assets and will release the valuation allowance when there is sufficient positive evidence to support a conclusion that it is more likely than not the deferred tax assets will be realized.