What changed in this filing

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Item 7A. Quantitative and Qualitative Disclosures About Market Risk

2024-03-21 compared with 2023-03-27 · 191 added, 241 removed, 1001 unchanged (30% of the section changed)

11 unchanged sentences

We do not enter into investments for trading or speculative purposes and have not used any derivative financial instruments to manage our interest rate risk exposure.

We had no exposure to changes in interest rates from debt obligations at January 31, 2023 as our 2023 Notes and 2024 Notes (the “Notes”) were issued at fixed rates of 0.5% and 0.0%, respectively.

The fair value of the Notes changes when the market price of our stock fluctuates or interest rates change.

However, we carry the Notes at face value less unamortized discount on our balance sheet and present the fair value for required disclosure purposes only.

We had no exposure to changes in interest rates from the Notes as of January 31, 2024 since the Notes were extinguished during fiscal 2024.

Additionally, our revolving credit facility, which is undrawn as of January 31, 2024, can be borrowed based on floating interest rate indexes, thus exposing us to potential interest rate fluctuations should we decide to access the facility.

Foreign Currency Exchange Risk

8 unchanged sentences

Foreign currency translation adjustments are accounted for as a component of “Accumulated other comprehensive loss” within “Stockholders’ equity”.

Gains or losses due to remeasurements of transactions denominated in foreign currencies are included in “Interest income and other income, net” in our consolidated statements of operations and comprehensive loss.

We have not engaged in the hedging of foreign currency transactions to date, although we may choose to do so in the future.

6 unchanged sentences

Consolidated Balance Sheets as of January 31, 2024 and 2023

Consolidated Statements of Operations and Comprehensive Loss for the Years Ended January 31, 2023 , 2022 and 2021

Consolidated Statements of Operations and Comprehensive I ncome ( Loss ) for the Years Ended January 31, 2024 , 2023 and 2022

Consolidated Statements of Stockholders’ Equity for the Years Ended January 31, 2024 , 2023 and 2022

10 unchanged sentences

Restructuring and Other Related Charges

Net Loss Per Share Attributable to Common Stockholders

Net Income ( Loss ) Per Share Attributable to Common Stockholders

Employee Benefit Plan

6 unchanged sentences

We have audited the accompanying consolidated balance sheets of DocuSign, Inc.

and its subsidiaries (the “Company”) as of January 31, 2023 and 2022, and the related consolidated statements of operations and comprehensive loss, of stockholders’ equity and of cash flows for each of the three years in the period ended January 31, 2023, including the related notes (collectively referred to as the “consolidated financial statements”).

and its subsidiaries (the “Company”) as of January 31, 2024 and 2023, and the related consolidated statements of operations and comprehensive income (loss), of stockholders’ equity and of cash flows for each of the three years in the period ended January 31, 2024, including the related notes (collectively referred to as the “consolidated financial statements”).

We also have audited the Company's internal control over financial reporting as of January 31, 2024, based on criteria established in Internal Control - Integrated Framework (2013) issued by the Committee of Sponsoring Organizations of the Treadway Commission (COSO).

75 unchanged sentences

Total current liabilities 1,660,621 2,208,322

Convertible senior notes, net—noncurrent — 718,487

Contract liabilities—noncurrent 21,980 16,925

22 unchanged sentences

DOCUSIGN, INC.

CONSOLIDATED STATEMENTS OF OPERATIONS AND COMPREHENSIVE LOSS

CONSOLIDATED STATEMENTS OF OPERATIONS AND COMPREHENSIVE INCOME (LOSS)

Year Ended January 31,

14 unchanged sentences

Total operating expenses 2,157,627 2,067,858 1,702,646

Loss from operations ( 88,031 ) ( 61,884 ) ( 173,855 )

Income (loss) from operations 31,634 ( 88,031 ) ( 61,884 )

Interest expense ( 6,844 ) ( 6,389 ) ( 6,443 )

Loss on extinguishment of debt — — ( 33,752 )

Interest income and other income, net 68,889 4,539 1,413

Loss before provision for income taxes ( 89,881 ) ( 66,914 ) ( 229,492 )

Income (loss) before provision for income taxes 93,679 ( 89,881 ) ( 66,914 )

Provision for income taxes 19,699 7,573 3,062

Net loss $ ( 97,454 ) $ ( 69,976 ) $ ( 243,267 )

Net loss per share attributable to common stockholders, basic and diluted $ ( 0.49 ) $ ( 0.36 ) $ ( 1.31 )

Weighted-average number of shares used in computing net loss per share attributable to common stockholders, basic and diluted 200,903 196,675 185,760

Net income (loss) $ 73,980 $ ( 97,454 ) $ ( 69,976 )

Net income (loss) per share attributable to common stockholders:

Basic $ 0.36 $ ( 0.49 ) $ ( 0.36 )

Diluted $ 0.36 $ ( 0.49 ) $ ( 0.36 )

Weighted-average shares used in computing net income (loss) per share:

Basic 204,070 200,903 196,675

Diluted 208,950 200,903 196,675

Other comprehensive income (loss):

Foreign currency translation gains (losses), net of tax $ ( 15,336 ) $ ( 7,935 ) $ 7,468

Unrealized losses on investments, net of tax ( 2,851 ) ( 1,838 ) ( 831 )

Foreign currency translation losses, net of tax $ ( 254 ) $ ( 15,336 ) $ ( 7,935 )

Unrealized gains (losses) on investments, net of tax 3,890 ( 2,851 ) ( 1,838 )

Other comprehensive income (loss) 3,636 ( 18,187 ) ( 9,773 )

Comprehensive loss $ ( 115,641 ) $ ( 79,749 ) $ ( 236,630 )

Comprehensive income (loss) $ 77,616 $ ( 115,641 ) $ ( 79,749 )

Stock-based compensation expense included in costs and expenses:

12 unchanged sentences

Balances at January 31, 2021 192,807 $ 19 $ 1,702,254 $ ( 1,048 ) $ 4,964 $ ( 1,380,452 ) $ 325,737

Cumulative impact of Accounting Standards Update 2020-06 adoption — — ( 86,144 ) — — 12,239 ( 73,905 )

Settlement of convertible senior notes due in 2023 749 — ( 873 ) — — — ( 873 )

Reclassification to mezzanine equity for convertible senior notes due in 2023 — — ( 3,390 ) — — — ( 3,390 )

Equity component of issued convertible senior notes due in 2024 — — 63,268 — — — 63,268

Purchase of capped calls related to issuance of convertible senior notes due in 2024 — — ( 31,395 ) — — — ( 31,395 )

Issuance of common stock as consideration for acquisition 247 — 48,361 — — — 48,361

Exercise of stock options 1,693 — 23,729 — — — 23,729

2 unchanged sentences

Employee stock purchase plan 264 — 46,077 — — — 46,077

Employee stock-based compensation expense — — 294,554 — — — 294,554

Charitable donation of common stock 10 — 3,000 — — — 3,000

Employee stock-based compensation — — 420,886 — — — 420,886

Net loss — — — — — ( 69,976 ) ( 69,976 )

Other comprehensive income, net — — — — 6,637 — 6,637

Other comprehensive loss, net — — — — ( 9,773 ) — ( 9,773 )

Balances at January 31, 2022 198,834 20 1,720,013 ( 1,532 ) ( 4,809 ) ( 1,438,189 ) 275,503

Cumulative impact of Accounting Standards Update 2020-06 adoption — — ( 86,144 ) — — 12,239 ( 73,905 )

Settlement of convertible senior notes due in 2023 749 — ( 873 ) — — — ( 873 )

Exercise of stock options 868 — 12,678 — — — 12,678

2 unchanged sentences

Employee stock purchase plan 535 — 36,526 — — — 36,526

Charitable donation of common stock 10 — 3,000 — — — 3,000

Employee stock-based compensation expense — — 420,886 — — — 420,886

Repurchases of common stock ( 1,135 ) — — — — ( 63,041 ) ( 63,041 )

Employee stock-based compensation — — 560,415 — — — 560,415

Net loss — — — — — ( 97,454 ) ( 97,454 )

Other comprehensive income, net — — — — ( 9,773 ) — ( 9,773 )

Other comprehensive loss, net — — — — ( 18,187 ) — ( 18,187 )

Balances at January 31, 2023 201,904 $ 20 $ 2,240,732 $ ( 1,785 ) $ ( 22,996 ) $ ( 1,598,684 ) $ 617,287

3 unchanged sentences

CONSOLIDATED STATEMENTS OF STOCKHOLDERS’ EQUITY (Continued)

Common Stock Additional Paid-In Capital Treasury Stock Accumulated Other Comprehensive Income (Loss) Accumulated Deficit Total Stockholders’ Equity

Common Stock Additional Paid-In Capital Treasury Stock Accumulated Other Comprehensive Income (Loss)

Accumulated Deficit Total Stockholders’ Equity

(in thousands) Shares Amount

Balances at January 31, 2023 201,904 20 2,240,732 ( 1,785 ) ( 22,996 ) ( 1,598,684 ) 617,287

Settlement of convertible senior notes due in 2024 — — 104 — — — 104

Exercise of stock options 840 — 13,991 — — — 13,991

3 unchanged sentences

Repurchases of common stock ( 3,058 ) — — — — ( 145,515 ) ( 145,515 )

Employee stock-based compensation expense — — 560,415 — — — 560,415

Net loss — — — — — ( 97,454 ) ( 97,454 )

Other comprehensive loss, net — — — — ( 18,187 ) — ( 18,187 )

Settlement of capped calls, net of related costs — — 23,688 — — — 23,688

Employee stock-based compensation — — 651,947 — — — 651,947

Net income — — — — — 73,980 73,980

Other comprehensive income, net — — — — 3,636 — 3,636

Balances at January 31, 2024 205,326 $ 21 $ 2,821,461 $ ( 2,164 ) $ ( 19,360 ) $ ( 1,670,219 ) $ 1,129,739

6 unchanged sentences

Cash flows from operating activities:

Net loss $ ( 97,454 ) $ ( 69,976 ) $ ( 243,267 )

Adjustments to reconcile net loss to net cash provided by operating activities

Net income (loss) $ 73,980 $ ( 97,454 ) $ ( 69,976 )

Adjustments to reconcile net income (loss) to net cash provided by operating activities

Depreciation and amortization 95,062 86,255 81,913

1 unchanged sentence

Amortization of debt discount and transaction costs 4,749 4,970 5,098

Loss on extinguishment of debt — — 33,752

Operating cash flow related to repayments of convertible senior notes — — ( 75,165 )

Non-cash operating lease costs 21,310 27,501 26,819

20 unchanged sentences

Purchases of property and equipment ( 92,391 ) ( 77,654 ) ( 61,396 )

Net cash (used in) provided by investing activities ( 191,197 ) ( 162,909 ) 81,229

Net cash provided by (used in) investing activities 44,612 ( 191,197 ) ( 162,909 )

Cash flows from financing activities:

Proceeds from issuance of convertible senior notes, net of initial purchasers' discounts and transaction costs — — 677,370

Purchase of capped calls related to issuance of convertible senior notes — — ( 31,395 )

Repayments of convertible senior notes ( 726,979 ) ( 16 ) ( 77,906 )

Repurchases of common stock ( 145,515 ) ( 63,041 ) —

Payment of revolving credit facility costs — — ( 2,453 )

Payment of tax withholding obligation on RSU settlement and ESPP purchase ( 84,403 ) ( 386,521 ) ( 372,463 )

Settlement of capped calls, net of related costs 23,688 — —

Payment of tax withholding obligation on net RSU settlement and ESPP purchase ( 144,218 ) ( 84,403 ) ( 386,521 )

Proceeds from exercise of stock options 13,991 12,678 23,729

18 unchanged sentences

Operating lease right-of-use assets exchanged for lease obligations 3,149 63,086 2,749

Fair value of shares issued as consideration for acquisition — — 48,361

Fair value of shares issued as part of the repayments of convertible senior notes — 2 174,230

8 unchanged sentences

We merged with and into DocuSign, Inc., a Delaware corporation, in March 2015.

DocuSign is the global leader in the eSignature category.

We offer products that address broader agreement workflows, and digital transformation, including the world’s leading electronic signature product, enabling agreements to be signed electronically on a wide variety of devices, from virtually anywhere in the world, securely.

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.

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.

Basis of Presentation and Principles of Consolidation

5 unchanged sentences

References to fiscal 2024, for example, are to the fiscal year ended January 31, 2024.

Certain prior year amounts have been reclassified to conform to current year presentation.

These amounts were not material to any of the periods presented.

Use of Estimates

3 unchanged sentences

• the average period of benefit associated with deferred contract acquisition costs and fulfillment costs;

• the valuation of strategic investments;

• the fair value of certain stock awards issued;

2 unchanged sentences

• the discount rate used for operating leases;

• the recognition and measurement of loss contingencies;

• the recognition, measurement and valuation of deferred income taxes.

64 unchanged sentences

The period of benefit for commissions paid for the acquisition of the initial subscription contract, of five years , is determined by taking into consideration our initial estimated customer life and the technological life of our software platform and related significant features.

The period of benefit for renewal subscription contracts, of two years , is determined by considering the average contractual term for renewal contracts.

The period of benefit for renewal subscription contracts, of two years , is determined by the weighted average contractual term for renewal contracts.

Commissions paid on professional services contracts are amortized over the period of benefit, being the period the associated revenue is earned as the commissions paid on new and renewal professional services contracts are commensurate with each other.

Amortization of deferred contract acquisition costs is primarily included in the “Sales and marketing” expense in the consolidated statements of operations and comprehensive loss.

Amortization of deferred contract acquisition costs is primarily included in the “Sales and marketing” expense in the consolidated statements of operations and comprehensive income (loss).

We periodically review these deferred costs to determine whether events or changes in circumstances have occurred that could impact the period of benefit of these deferred contract acquisition costs.

7 unchanged sentences

“Professional services and other” cost of revenue consists primarily of personnel costs for our professional services delivery team, travel-related costs and allocated overhead.

Advertising costs are expensed as incurred and are included in “Sales and marketing” expense in our consolidated statements of operations and comprehensive loss.

Advertising costs are expensed as incurred and are included in “Sales and marketing” expense in our consolidated statements of operations and comprehensive income (loss).

Advertising expense was $ 95.0 million, $ 128.3 million and $ 115.7 million in the years ended January 31, 2024, 2023 and 2022.

26 unchanged sentences

Nonmonetary assets and liabilities are not remeasured.

We recognize gains and losses from such adjustments within “Interest income and other income, net” in the consolidated statements of operations and comprehensive loss in the period of occurrence.

We recognize gains and losses from such adjustments within “Interest income and other income, net” in the consolidated statements of operations and comprehensive income (loss) in the period of occurrence.

We present our financial statements in U.S.

Adjustments resulting from translating foreign functional currency financial statements into U.S.

dollars are recorded as a separate component on our consolidated statements of comprehensive loss, net of tax.

dollars are recorded as a separate component on our consolidated statements of comprehensive income (loss), net of tax.

All assets and liabilities denominated in a foreign currency are translated at the exchange rate on the balance sheet date.

1 unchanged sentence

Equity transactions are translated using the historical exchange rate.

Net Loss Per Share Attributable to Common Stockholders

In periods when we have net income, we compute basic and diluted net loss per share in conformity with the two-class method required for participating securities.

Net Income (Loss) Per Share Attributable to Common Stockholders

In periods when we have net income, we compute basic and diluted net income per share in conformity with the two-class method required for participating securities.

The undistributed earnings are allocated between common stock and participating securities as if all earnings had been distributed during the period presented.

We consider any shares issued on the early exercise of stock options subject to repurchase to be participating securities because holders of such shares have non-forfeitable dividend rights in the event a dividend is paid on common stock.

The holders of early exercised shares do not have a contractual obligation to share in our losses.

As such, our net losses in all the years presented were not allocated to these participating securities.

Basic net loss per share attributable to common stockholders is computed by dividing the net loss attributable to common stockholders by the weighted-average number of shares of common stock outstanding during the period.

Diluted net loss per share attributable to common stockholders is computed by giving effect to all potential shares of common stock, including shares underlying our convertible senior notes, unvested RSUs, early exercised or outstanding stock options, ESPP purchase rights, convertible preferred stock, and warrants to purchase common stock and convertible preferred stock, to the extent they are dilutive.

Since we have reported net losses for all periods presented, dilutive common shares are not assumed to have been issued as their effect would have been antidilutive.

Basic net income (loss) per share attributable to common stockholders is computed by dividing the net income (loss) attributable to common stockholders by the weighted-average number of shares of common stock outstanding during the period.

Diluted net income per share attributable to common stockholders is computed by giving effect to all potential shares of common stock, including shares underlying our convertible senior notes, unvested stock awards, outstanding stock options, ESPP purchase rights, convertible preferred stock, and warrants to purchase common stock and convertible preferred stock, to the extent they are dilutive.

The dilutive potential shares of common stock are computed using the treasury stock method or the as-if converted method, as applicable.

For periods presented in which we have reported net losses, dilutive common shares are not assumed to have been issued as their effect would have been antidilutive.

Therefore, diluted net loss per share attributable to common stockholders is the same as basic net loss per share attributable to common stockholders.

1 unchanged sentence

Cash and cash equivalents consist of money market funds, highly liquid investments with original maturities of three months or less at the date of purchase and deposits with financial institutions and are carried at fair value.

Investments in marketable securities consist of commercial paper, corporate notes and bonds, as well as U.S.

Investments in marketable securities consist of commercial paper, corporate notes and bonds, municipal notes and bonds, as well as U.S.

Treasury and government agency securities.

13 unchanged sentences

Restricted Cash

Restricted cash consists of certificates of deposits collateralizing our operating lease agreements for office space and cash withheld from employees to fund claims and program expenses related to the Voluntary Disability Plans in California and Washington.

Restricted cash consists primarily of certificates of deposits collateralizing our operating lease agreements for office space and cash withheld from employees to fund claims and program expenses related to the Voluntary Disability Plans in California.

The following table illustrates the reconciliation of cash, cash equivalents, and restricted cash shown in the consolidated statements of cash flows as of January 31, 2024, 2023, and 2022:

20 unchanged sentences

DocuSign, Inc.| 2024 Form 10-K | 73

Accounts Receivable and Allowance for Doubtful Accounts and Credit Losses

Accounts Receivable and Credit Losses

Accounts receivable primarily consist of amounts billed currently due from customers.

14 unchanged sentences

Leasehold improvements Lesser of lease term and 10 years

Disposals are removed at cost less accumulated depreciation, and any gain or loss from disposition is reflected in the statement of operations and comprehensive loss in the year of disposition.

Disposals are removed at cost less accumulated depreciation, and any gain or loss from disposition is reflected in the statement of operations and comprehensive income (loss) in the year of disposition.

Additions and improvements that increase the value or extend the life of an asset are capitalized.

15 unchanged sentences

Operating leases are classified in “Operating lease right-of-use assets”, “Operating lease liabilities—current”, and “Operating lease liabilities—noncurrent” on our consolidated balance sheets.

Operating lease expense is recognized on a straight-line basis over the expected lease term and included in “Loss from operations” in our consolidated statements of operations and comprehensive loss.

Operating lease expense is recognized on a straight-line basis over the expected lease term and included in “Income (loss) from operations” in our consolidated statements of operations and comprehensive income (loss).

We did not have material finance leases for all periods presented.

DocuSign, Inc.| 2024 Form 10-K | 74

34 unchanged sentences

During the measurement period, not to exceed one year from the date of acquisition, we may record adjustments to the assets acquired and liabilities assumed, with a corresponding offset to goodwill if new information is obtained related to facts and circumstances that existed as of the acquisition date.

After the measurement period, any subsequent adjustments are reflected in the consolidated statements of operations and comprehensive loss.

After the measurement period, any subsequent adjustments are reflected in the consolidated statements of operations and comprehensive income (loss).

Acquisition costs, such as legal and consulting fees, are expensed as incurred.

18 unchanged sentences

The cost incurred in connection with the capped calls was recorded as a reduction to additional paid-in capital.

Subsequent unwinding of capped calls was recorded as an increase to cash and additional paid-in capital upon settlement.

Legal Contingencies

2 unchanged sentences

A determination of the amount of the liabilities required, if any, for these contingencies is made after the analysis of each separate matter.

Recently Adopted Accounting Pronouncements

We have not adopted accounting pronouncements during the year ended January 31, 2023.

DocuSign, Inc.| 2024 Form 10-K | 76

Subscription revenue is recognized over time and accounted for approximately 97 %, 97 % and 95 % of our revenue for the years ended January 31, 2023, 2022 and 2021.

Recent Accounting Pronouncements

In November 2023, the Financial Accounting Standards Board (“FASB”) issued Accounting Standards Update No.

2023-07, “Segment Reporting (Topic 280):

Improvements to Reportable Segment Disclosures” (“ASU 2023-07”), which enhances disclosures required for operating segments.

ASU 2023-07 expands public entities’ segment disclosures by requiring disclosure of significant segment expenses that are regularly provided to the chief operating decision maker and included within each reported measure of segment profit or loss, an amount and description of its composition for other segment items, and interim disclosures of a reportable segment’s profit or loss and assets.

All disclosure requirements of ASU 2023-07 are required for entities with a single reportable segment.

ASU 2023-07 is effective for the Company’s fiscal year beginning February 1, 2024, and interim periods for the fiscal year beginning February 1, 2025, and should be applied on a retrospective basis to all periods presented.

We are currently evaluating the effect of adopting ASU 2023-07 on our financial statement disclosures.

In December 2023, the FASB issued Accounting Standards Update 2023-09, “Income Taxes (Topic 740):

Improvements to Income Tax Disclosures” (“ASU 2023-09”), amending existing income tax disclosure guidance, primarily requiring more detailed disclosure for income taxes paid and the effective tax rate reconciliation.

ASU 2023-09 is effective for annual reporting periods beginning after December 15, 2024, with early adoption permitted and can be applied on either a prospective or retrospective basis.

We are currently evaluating the effect of adopting ASU 2023-09 on our income tax disclosures.

We have not adopted accounting pronouncements during the year ended January 31, 2024.

Subscription revenue is recognized over time and accounted for approximately 97 % of our revenue in each of the years ended January 31, 2024, 2023 and 2022.

Performance Obligations

As of January 31, 2024, the amount of the transaction price allocated to remaining performance obligations for contracts greater than one year was $ 2.2 billion.

We expect to recognize 57 % of the transaction price allocated to remaining performance obligations within the 12 months following January 31, 2023 in our consolidated statement of operations and comprehensive loss.

We expect to recognize 56 % of the transaction price allocated to remaining performance obligations within the 12 months following January 31, 2024 in our consolidated statement of operations and comprehensive income (loss).

Contract Balances

2 unchanged sentences

The change in contract assets reflects the difference in timing between our satisfaction of remaining performance obligations and our contractual right to bill our customers.

Contract liabilities consist of deferred revenue and include payments received in advance of performance under the contract.

Contract liabilities consist of deferred revenue and payments received in advance of performance under the contract.

Such amounts are generally recognized as revenue over the contractual period.

For the years ended January 31, 2023 , 2022 and 2021, we recognized revenue of $ 1.0 billion , $ 773.7 million and $ 499.5 million that was included in the corresponding contract liability balance at the beginning of the periods presented.

For the years ended January 31, 2024 , 2023 and 2022, we recognized reve nue of $ 1.2 billion, $ 1.0 billion and $ 773.7 million that was included in the corresponding contract liability balance at the beginning of the periods presented.

We receive payments from customers based upon contractual billing schedules.

1 unchanged sentence

Payment terms on invoiced amounts are typically 30 days.

DocuSign, Inc.| 2024 Form 10-K | 77

Fair Value Measurements

6 unchanged sentences

Commercial paper 43,845 — ( 9 ) 43,836

government agency securities 9,968 — ( 1 ) 9,967

Available-for-sale securities

1 unchanged sentence

Corporate notes and bonds 299,166 262 ( 670 ) 298,758

Municipal notes and bonds 7,983 — ( 65 ) 7,918

governmental securities 28,752 — ( 66 ) 28,686

1 unchanged sentence

Total $ 723,206 $ 264 $ ( 771 ) $ 722,699

DocuSign, Inc.| 2023 Form 10-K | 74

January 31, 2023

7 unchanged sentences

Corporate notes and bonds 367,930 101 ( 3,771 ) 364,260

Municipal notes and bonds 7,983 — ( 65 ) 7,918

governmental securities 38,344 4 ( 405 ) 37,943

4 unchanged sentences

The fair value of our Level 2 investments is determined using pricing based on quoted market prices or alternative market observable inputs .

DocuSign, Inc.| 2024 Form 10-K | 78

The fair value of our available-for-sale securities as of January 31, 2024, by remaining contractual maturities, were as follows (in thousands):

9 unchanged sentences

During the year ended January 31, 2023, the value of these investments decreased $ 3.7 million, net.

During the year ended January 31, 2022, the value of these investments increased $ 4.8 million.

Convertible Senior Notes

We estimated the fair value based on the estimated or actual bids and offers of the Notes in an over-the-counter market on the last trading day of the reporting period (Level 2).

The Notes are recorded at face value less unamortized debt discount and transaction costs as “Convertible senior notes, net—noncurrent” and “Convertible senior notes—current.” Refer to Note 8 for further information.

DocuSign, Inc.| 2023 Form 10-K | 75

(in thousands) 2023 2022

As of January 31, 2024, the 2023 Notes and 2024 Notes had been extinguished.

As of January 31, 2023, we estimated the fair value based on the estimated or actual bids and offers of the Notes in an over-the-counter market on the last trading day of the reporting period (Level 2), and the Notes were recorded at face value less unamortized debt discount and transaction costs as “Convertible senior notes—current.” Refer to Note 7 for further information.

(in thousands) January 31, 2023

0.5 % Convertible Senior Notes due in 2023

16 unchanged sentences

$ 245,173 $ 199,892

DocuSign, Inc.| 2024 Form 10-K | 79

Depreciation and amortization expenses associated with property and equipment was $ 75.7 million, $ 65.5 million and $ 57.1 million in the years ended January 31, 2024, 2023 and 2022.

This included amortization expense related to capitalized internally-developed software costs of $ 35.1 million, $ 19.7 million and $ 10.3 million in the respective years .

We capitalized $ 66.1 million, $ 39.0 million and $ 29.3 million of internally developed software costs, including $ 19.2 million, $ 9.8 million and $ 7.2 million of capitalized stock-based compensation in the years ended January 31, 2023, 2022 and 2021.

Acquisition of Seal Software Group Limited

On May 1, 2020, we completed the acquisition of Seal Software Group Limited (“Seal”), a contract analytics and artificial intelligence (“AI”) technology provider headquartered in Walnut Creek, California.

The acquisition allows us to integrate Seal's technology comprehensively across the DocuSign Agreement Cloud to deliver increased functionality to companies using the Agreement Cloud to prepare, sign, act on and manage agreements.

Under the terms of the purchase agreement, we paid $ 184.7 million in cash, net of cash acquired, transaction costs and working capital adjustments, for Seal’s outstanding stock.

We accounted for the transaction as a business combination using the acquisition method of accounting.

We allocated the purchase price to the tangible and identifiable intangible assets acquired and liabilities assumed based on their respective estimated fair values on the acquisition date.

Fair values were determined using the income and cost approaches.

Excess purchase price consideration was recorded as goodwill and is primarily attributable to the assembled workforce and expanded market opportunities when integrating Seal’s AI and analytics capabilities within our existing product offering.

DocuSign, Inc.| 2023 Form 10-K | 76

In the year ended January 31, 2021, we recognized revenues from Seal of $ 16.3 million and net losses of $ 20.1 million, excluding the impact of acquired intangible asset amortization.

The results of operations of Seal were included in our consolidated statements of operations from the acquisition date.

The following unaudited pro forma information has been prepared for illustrative purposes only and assumes the acquisition occurred on February 1, 2019.

It includes pro forma adjustments related to the amortization of acquired intangible assets, share-based compensation expense, professional services revenue and contract acquisitions costs adjustments under the new revenue recognition standard, and contract liabilities fair value adjustment.

The unaudited pro forma results have been prepared based on estimates and assumptions, which we believe are reasonable, however, they are not necessarily indicative of the consolidated results of operations had the acquisition occurred on February 1, 2019, or of future results of operations:

Year Ended January 31,

(in thousands) (unaudited) 2021

Revenue $ 1,464,424

Net loss ( 246,819 )

Acquisition of Liveoak Technologies, Inc.

On July 6, 2020, we completed the acquisition of Liveoak Technologies, Inc.

(“Liveoak”), a virtual customer engagement and business platform based in Austin, Texas.

The company’s platform includes several technologies specific to remote agreements, such as video conferencing, video identity verification, collaborative form-filling, an integration with DocuSign eSignature, and a detailed audit trail.

The acquisition enables us to leverage Liveoak’s technology and expertise to accelerate the launch of DocuSign Notary, a new product for remote online notarization, where signers and the notary public are in different places.

The consideration to acquire Liveoak’s outstanding stock was $ 48.4 million, which consisted primarily of the fair value of our common stock issued and the fair value of stock options issued to substitute vested Liveoak options.

We included the results of operations of Liveoak in our consolidated statements of operations from the acquisition date.

These results, including pro forma information, were not material to our consolidated statements of operations for the year ended January 31, 2021 .

We capitalized $ 95.3 million, $ 66.1 million and $ 39.0 million of internally developed software costs, including $ 30.8 million, $ 19.2 million and $ 9.8 million of capitalized stock-based compensation in the years ended January 31, 2024, 2023 and 2022, respectively.

Goodwill and Intangible Assets, Net

1 unchanged sentence

Balance at January 31, 2022 $ 355,058

Additions—Seal 1,185

Additions—Clause 4,100

Foreign currency translation ( 1,439 )

2 unchanged sentences

Balance at January 31, 2024 $ 353,138

DocuSign, Inc.| 2023 Form 10-K | 77

Intangible assets consisted of the following:

41 unchanged sentences

The net proceeds from the issuance of the 2024 Notes were $ 677.3 million after deducting the initial purchasers’ discounts and transaction costs.

The Notes are senior unsecured obligations and rank senior in right of payment to any of our indebtedness that is expressly subordinated in right of payment to the Notes;

When outstanding, the Notes were senior unsecured obligations and ranked senior in right of payment to any of our indebtedness that was expressly subordinated in right of payment to the Notes;

equal in right of payment to any of our unsecured indebtedness then existing and future liabilities that are not so subordinated;

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and structurally junior to all indebtedness and other liabilities (including trade payables) of our subsidiaries.

Upon conversion of the Notes, holders will receive cash, shares of our common stock or a combination of cash and shares of our common stock, at our election.

The 2023 Notes are governed by an indenture dated September 18, 2018 (the “2018 Indenture”).

The 2024 Notes are governed by an indenture dated January 15, 2021 (the “2021 Indenture,” and together with the 2018 Indenture, the “Indentures”).

The Indentures are between us, as the issuer, and U.S.

The 2023 Notes were governed by an indenture dated September 18, 2018 (the “2018 Indenture”).

The 2024 Notes were governed by an indenture dated January 15, 2021 (the “2021 Indenture,” and together with the 2018 Indenture, the “Indentures”).

The Indentures were between us, as the issuer, and U.S.

Bank National Association, as trustee.

The Indentures do not contain any financial covenants or restrictions on the payments of dividends, the incurrence of indebtedness, or the issuance or repurchase of securities by us or any of our subsidiaries.

The 2023 Notes mature on September 15, 2023, unless earlier repurchased or redeemed by us or earlier converted in accordance with their terms prior to the maturity date.

Interest on the 2023 Notes is payable semi-annually in arrears on March 15 and September 15 of each year.

The Notes are subject to additional interest in certain events of default.

The 2024 Notes mature on January 15, 2024 unless earlier repurchased by us or earlier converted in accordance with their terms prior to the maturity date.

DocuSign, Inc.| 2023 Form 10-K | 79

Conversion terms

The 2023 Notes have an initial conversion rate of 13.9860 shares of our common stock per $1,000 principal amount of the 2023 Notes, which is equal to an initial conversion price of approximately $ 71.50 per share of our common stock.

The 2024 Notes have an initial conversion rate of 2.3796 shares of our common stock per $1,000 principal amount of the 2024 Notes, which is equal to an initial conversion price of approximately $ 420.24 per share of our common stock.

The initial conversation rates are subject to adjustment in some events.

Following certain corporate events that occur prior to the maturity date or, with respect to the 2023 Notes, following our issuance of a notice of redemption, we will increase the conversion rate for a holder who elects to convert its Notes in connection with such corporate event or during the related redemption period in certain circumstances.

Additionally, upon the occurrence of a corporate event that constitutes a “fundamental change” as defined within the respective Indentures, holders of the Notes may require us to repurchase for cash all or a portion of their Notes at a purchase price equal to 100 % of the principal amount of the Notes plus accrued and unpaid interest, if any.

No such corporate events have occurred as of January 31, 2023.

Holders of the 2023 Notes may convert all or any portion of their 2023 Notes at any time on or after June 15, 2023, until the close of business on September 13, 2023.

Prior to the close of business on the business day immediately preceding June 15, 2023, holders of the 2023 Notes may convert all or any portion of their 2023 Notes, in integral multiples of $1,000 principal amount, only under the following circumstances (the “2023 Notes conversion conditions”):

• During any fiscal quarter commencing after the fiscal quarter ending on January 31, 2019 (and only during such fiscal quarter), if the last reported sale price of our common stock for at least 20 trading days (whether or not consecutive) during a period of 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding fiscal quarter is greater than or equal to 130 % of the conversion price on each applicable trading day;

• During the 5 -business day period after any 10 consecutive trading day period (the “measurement period”) in which the trading price as defined in the 2018 Indenture per $1,000 principal amount of notes for each trading day of the measurement period was less than 98 % of the product of the last reported sale price of our common stock and the conversion rate on each such trading day;

• If we call any or all of the notes for redemption, at any time prior to the close of business on the scheduled trading day immediately preceding the redemption date;

• Upon the occurrence of specified corporate events described in the 2018 Indenture.

Based upon the reported sales price of our common stock, the 2023 Notes became convertible on August 1, 2020 and continued to be convertible through July 31, 2022.

As of January 31, 2023, the 2023 Notes did not meet the conversion terms and are not convertible.

Holders of the 2024 Notes may convert all or any portion of their 2024 Notes at any time on or after October 15, 2023, until the close of business on January 11, 2024.

Prior to the close of business on the business day immediately preceding October 15, 2023, holders of the 2024 Notes may convert all or any portion of their 2024 Notes, in integral multiples of $1,000 principal amount, only under the following circumstances (the “2024 Notes conversion conditions”):

• During any fiscal quarter commencing after the fiscal quarter ending on April 30, 2021 (and only during such fiscal quarter), if the last reported sale price of our common stock for at least 20 trading days (whether or not consecutive) during a period of 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding fiscal quarter is greater than or equal to 130 % of the conversion price on each applicable trading day;

• During the 5 -business day period after any 10 consecutive trading day period (the “measurement period”) in which the trading price as defined in the 2021 Indenture per $1,000 principal amount of notes for each trading day of the measurement period was less than 98 % of the product of the last reported sale price of our common stock and the conversion rate on each such trading day;

• Upon the occurrence of specified corporate events described in the 2021 Indenture.

As of January 31, 2023, the 2024 Notes conversion conditions described above were not met and therefore the 2024 Notes are not yet convertible.

Redemption terms

We may redeem for cash or shares all or any portion of the 2023 Notes, at our option, at a redemption price equal to 100 % of the principal amount of the notes to be redeemed, plus accrued and unpaid interest, beginning on or after September 20, 2021 if the last reported sale price of our common stock for at least 20 trading days (whether or not consecutive) during any period of 30 consecutive trading days ending on, and including, the trading day immediately preceding the date on which the Company provides the notice of redemption is greater than or equal to 130 % of the conversion price on each applicable trading day.

DocuSign, Inc.| 2023 Form 10-K | 80

We may not redeem the 2024 Notes prior to the maturity date.

Repurchases of the 2023 Notes

In connection with our issuance of the 2024 Notes in fiscal 2021, we used a portion of the proceeds to repurchase $ 460.0 million aggregate principal amount of the 2023 Notes in privately negotiated transactions for an aggregate consideration of $ 1.7 billion, consisting of $ 459.2 million in cash and 4.7 million shares of our common stock with a value of $ 1.2 billion, a non-cash financing activity.

We recorded an extinguishment loss of $ 33.8 million as a result of the transaction.

In our consolidated statement of cash flows, the cash paid to repurchase the 2023 Notes was bifurcated into two components:

the portion of the repayment attributable to accreted interest related to debt discount is classified as cash outflows from operating activities, and the portion of the repayment attributable to the principal is classified as cash outflows from financing activities.

The Indentures did not contain any financial covenants or restrictions on the payments of dividends, the incurrence of indebtedness, or the issuance or repurchase of securities by us or any of our subsidiaries.

The 2023 Notes matured on September 15, 2023.

Interest on the 2023 Notes was payable semi-annually in arrears on March 15 and September 15 of each year.

The Notes were subject to additional interest in certain events of default.

The 2024 Notes matured on January 15, 2024.

Conversions of the 2023 Notes

In January 2021, certain holders of the 2023 Notes exercised their option to convert $ 23.9 million aggregate amount of the principal of the 2023 Notes.

As the principal was settled in cash in March 2021, we reclassified $ 20.5 million of the carrying value to “Convertible senior notes—current” and $ 3.4 million, representing the difference between the aggregate principal and the carrying value, to mezzanine equity from permanent equity on our consolidated balance sheet as of January 31, 2021.

During the year ended January 31, 2022, we settled $ 77.9 million aggregate amount of the principal of 2023 Notes, for aggregate consideration of $ 252.1 million, consisting of $ 77.9 million in cash and 0.7 million shares of our common stock with a value of $ 174.2 million.

The $ 0.9 million excess of the cash consideration over the corresponding carrying value was recorded as a reduction to additional paid-in capital.

DocuSign, Inc.| 2024 10-K | 81

Extinguishment of the 2023 Notes and 2024 Notes

We repaid in cash $ 37.1 million and $ 689.9 million in aggregate principal amount of the 2023 Notes and 2024 Notes respectively during the year ended January 31, 2024.

Net Carrying Amounts of the Liability Components

The 2023 Notes and 2024 Notes are within one year of maturity and are therefore classified as current liabilities in our consolidated balance sheets as of January 31, 2023.

As of January 31, 2024, the 2023 Notes and 2024 Notes had been extinguished, and all outstanding amounts were repaid in full.

As of January 31, 2023, the 2023 Notes and 2024 Notes were within one year of maturity and were therefore classified as current liabilities in our consolidated balance sheets.

The net carrying amounts of the Notes were as follows:

(in thousands) 2024 2023

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Principal $ 690,000 $ 690,000

extinguishment or conversion ( 690,000 ) —

Unpaid principal — 690,000

unamortized transaction costs — ( 4,078 )

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Excess of if-converted value over principal $ — $ —

DocuSign, Inc.| 2023 Form 10-K | 81

Interest expense recognized related to the Notes was as follows:

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Contractual interest expense $ 425 $ 185 $ 168

Amortization of debt discount — — 25,828

Amortization of transaction costs 4,197 4,415 4,544

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To minimize the potential economic dilution to our common stock upon conversion of the Notes, we entered into privately-negotiated capped call transactions ("Capped Calls") with certain counterparties.

The capped call transactions were as follows:

(in thousands, except per share amounts) 2023 Notes 2024 Notes

Aggregate cost of capped calls $ 67,563 $ 31,395

Initial strike price per share (1)

$ 71.50 $ 420.24

Initial cap price per share (1)

$ 110.00 $ 525.30

Shares of our common stock covered by the capped calls (1)

(1) Subject to adjustments for certain events, such as merger events and tender offers, and anti-dilution adjustments

Impact on Loss Per Share

Upon adoption of ASU 2020-06 on February 1, 2021, in periods when we have net income, the shares of our common stock subject to the Notes outstanding during the period are included in our diluted earnings per share under the if-converted method.

Prior to the adoption of ASU 2020-06, had we had net income, the shares of our common stock subject to the Notes outstanding during the period would have been included in our diluted earnings per share.

In the fourth quarter of 2021, share settlement was presumed leading to the application of the if-converted method.

In periods before that, cash settlement was presumed and shares subject to the Notes would have been included under the treasury stock method.

In the first quarter of fiscal 2024, we unwound $ 23.7 million of the Capped Calls in relation to our 2023 Notes and received cash from the counterparties.

All remaining Capped Calls associated with the 2023 Notes and 2024 Notes expired during the year ended January 31, 2024.

DocuSign, Inc.| 2024 10-K | 82

Impact on Net Income (Loss) Per Share

In periods when we have net income, the shares of our common stock subject to the Notes outstanding during the period are included in our diluted earnings per share under the if-converted method.

Capped Calls are excluded from the calculation of diluted earnings per share, as they would be antidilutive.

However, upon conversion, there will be no economic dilution from the Notes unless the market price of our common stock exceeds the cap prices listed above in the Capped Calls section, as exercise of the Capped Calls offsets any dilution from the Notes from the conversion price up to the cap price.

However, upon conversion, there will be no economic dilution from the Notes unless the market price of our common stock exceeds the initial $ 110.00 per share cap price associated with the 2023 Notes and $ 525.30 per share cap price associated with the 2024 Notes, as exercise of the Capped Calls offsets any dilution from the Notes from the conversion price up to the cap price.

As of January 31, 2024 and 2023, the market price of our common stock did not exceed the $ 110.00 per share cap price associated with the 2023 Notes or the $ 525.30 cap price associated with the 2024 notes.

Therefore, the Notes would not have caused economic dilution if converted as of January 31, 2024 and 2023.

As of January 31, 2022, the market price of our common stock exceeded the $ 110.00 per share cap price associated with the 2023 Notes but not the $ 525.30 cap price associated with the 2024 notes.

Therefore, the 2023 Notes would have caused economic dilution if converted as of January 31, 2022.

As of January 31, 2023, the market price of our common stock did not exceed the $ 110.00 per share cap price associated with the 2023 Notes or the $ 525.30 cap price associated with the 2024 notes.

Therefore, the Notes would not have caused economic dilution if converted as of January 31, 2023.

Revolving Credit Facility

In January 2021, we entered into a credit agreement with a syndicate of banks.

In January 2021, we entered into a credit agreement, as subsequently amended in May 2023, with a syndicate of banks.

The credit agreement extended a senior secured revolving credit facility to us in an aggregate principal amount of $ 500.0 million, which amount may be increased by an additional $ 250.0 million subject to the terms of the credit agreement.

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The facility is subject to customary fees for loan facilities of this type, including ongoing commitment fees at a rate between 0.25 % and 0.30 % per annum on the daily undrawn balance.

DocuSign, Inc.| 2023 Form 10-K | 82

We lease offices under noncancelable operating lease agreements that expire at various dates through the end of July 2034.

As of January 31, 2023, we had no finance leases.

Some of our operating leases contain escalation provisions for adjustments in the consumer price index and options to renew.

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The discount rates for operating leases as of January 31, 2024 and 2023 were 4.7 % and 4.6 %.

DocuSign, Inc.| 2024 10-K | 83

Commitments and Contingencies

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Under the agreement, the minimum commitment is $ 175.0 million through fiscal 2028.

As of January 31, 2023, the remaining commitment was $ 157.1 million.

The remaining commitment is excluded from the table above.

DocuSign, Inc.| 2023 Form 10-K | 83

As of January 31, 2024, the remaining commitment, which is excluded from the table above, was $ 123.0 million.

Indemnification

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From time to time, we may be subject to legal proceedings, claims and litigation made against us in the ordinary course of business.

All legal costs associated with litigation are expensed as incurred.

Legal costs associated with litigation are expensed as incurred.

We believe the final outcome of these matters, including the case described below, will not have a material adverse effect on our business, consolidated financial position, results of operations or cash flows.

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DocuSign, Inc., et al., Case No.

3:22-cv-00824, naming DocuSign and certain of our current and former officers as defendants.

3:22-cv-00824, naming DocuSign and certain of our then-current and former officers as defendants.

An amended complaint was filed on July 8, 2022.

As amended, the suit purports to allege claims under Sections 10(b) and 20(a) of the Securities Exchange Act of 1934, and Rule 10b-5 promulgated thereunder, based on allegedly false and misleading statements about our business and prospects during the course of the COVID-19 pandemic.

As amended, the suit purports to allege claims under Sections 10(b) and 20(a) of the Securities Exchange Act of 1934, as amended, and Rule 10b-5 promulgated thereunder, based on allegedly false and misleading statements about our business and prospects during the course of the COVID-19 pandemic.

As amended, the suit is purportedly brought on behalf of purchasers of our securities between June 4, 2020 and June 9, 2022.

We moved to dismiss the amended complaint on September 16, 2022.

Our motion to dismiss the case at the pleading stage was denied by the U.S.

District Court on April 18, 2023 and the suit is now proceeding.

DocuSign, Inc.| 2024 10-K | 84

An earlier action alleging similar claims against the same defendants, captioned Collins v.

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3:22-cv-00851, filed in the Eastern District of New York and subsequently transferred to the Northern District of California, was voluntarily dismissed on February 14, 2022.

Four putative shareholder derivative cases have been filed containing allegations based on or similar to those in the securities class action (Weston).

Five putative shareholder derivative cases have been filed containing allegations based on or similar to those in the securities class action (Weston).

The cases were filed on May 17, 2022, in the U.S.

District Court for the District of Delaware, captioned Potteti v.

District Court for the District of Delaware, captioned Pottetti v.

Springer, et al., Case No.

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3:22-cv-02987;

and on September 20, 2022 in the U.S.

on September 20, 2022 in the U.S.

District Court for the Northern District of California, captioned Fox v.

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3:22-cv-05343;

and on March 7, 2024 in the Delaware Court of Chancery, captioned Roy v.

Alhadeff, et al., Case No.

2024-0223-JTL.

Each case is allegedly brought on the Company’s behalf.

The suits name the Company as a nominal defendant and, depending on the particular case, the members of our board of directors or, in certain instances, current or former officers, as defendants.

The suits name the Company as a nominal defendant and, depending on the particular case, the members of our board of directors or, in certain instances, then-current or former officers, as defendants.

While the complaints vary, they are based largely on the same underlying allegations as the securities class action suit described above (Weston), as well as, in certain instances, alleged insider trading.

Collectively, these lawsuits purport to assert claims for, among other things, breach of fiduciary duty, aiding and abetting such breach, corporate waste, unjust enrichment, and under Sections 10(b) and 21D of the Securities Exchange Act of 1934.

Collectively, these lawsuits purport to assert claims for, among other things, breach of fiduciary duty, aiding and abetting such breach, corporate waste, gross mismanagement, unjust enrichment, and under Sections 10(b) and 21D of the Securities Exchange Act of 1934.

The complaints seek to recover unspecified damages and other relief on the Company’s behalf.

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The third case in the Northern District of California (Fox) was related to the other derivative suits and assigned to the same judge, and was similarly stayed by order of the court on December 2, 2022.

The Delaware suit (Potteti) was voluntarily dismissed on September 1, 2022, and then re-filed in the Delaware Court of Chancery on September 22, 2022, under the caption Pottetti v.

The Delaware suit (Pottetti) was voluntarily dismissed on September 1, 2022, and then re-filed in the Delaware Court of Chancery on September 22, 2022, under the caption Pottetti v.

Springer, et al., Case No.

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The Delaware Court of Chancery issued an order on September 30, 2022 staying the action in light of the securities class action and no response to the complaint will be due unless and until the stay is lifted.

DocuSign, Inc.| 2023 Form 10-K | 84

We anticipate seeking a stay of the newly filed Delaware suit (Roy) on similar terms.

DocuSign Civil Litigation

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Springer’s resignation from our board of directors.

Springer’s complaint sought relief determining that he did not resign from his position on our board of director and remains a director, and for an award of attorneys’ fees and costs associated with the civil action.

Springer’s complaint sought relief determining that he did not resign from his position on our board of directors and remains a director, and for an award of attorneys’ fees and costs associated with the civil action.

To avoid the cost and distraction of further litigation with Mr.

Springer, the Company offered to stipulate to entry of judgment in favor of Mr.

Springer as to his disputed resignation and his status as a member of our Board.

Springer as to his disputed resignation and his status as a member of our board of directors.

Following our offer, on January 11, 2023, the Chancery Court issued an order declaring and confirming that (i) Mr.

Springer has not resigned from the Board and (ii) Mr.

Springer is currently a member of the Board.

Springer has not resigned from the board of directors and (ii) Mr.

Springer is currently a member of the board of directors.

Springer subsequently filed a motion seeking payment of his attorneys’ fees.

DocuSign has opposed this motion, which remains pending before the Chancery Court.

DocuSign has opposed this motion, which remains pending before the Delaware Court of Chancery.

In addition, on January 26, 2023, Mr.

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In the demand, Mr.

Springer alleges that he was wrongfully terminated as CEO;

Springer alleges that he was wrongfully terminated as Chief Executive Officer;

asserts related claims against DocuSign and Ms.

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and seeks unspecified damages and other relief.

DocuSign has engaged legal counsel to defend the matter, and on March 10, 2023 submitted a motion to dismiss several of the causes of action asserted in the demand.

The arbitration hearing for this case took place from March 11-15, 2024, and a final order from the arbitrator is expected on or before June 30, 2024.

DocuSign, Inc.| 2024 10-K | 85

Stockholders' Equity

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RSUs granted under the 2018 Plan generally vest over a four-year period, either quarterly or with 25 % vesting at the end of one year and the remainder quarterly thereafter.

Additionally, the Company grants performance-based and market-based RSUs to its executives on an annual basis.

DocuSign, Inc.| 2023 Form 10-K | 85

Additionally, we grant performance stock awards to our executives on an annual basis.

Shares available for grant under the 2018 Plan for the year ended January 31, 2024 was as follows:

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Shares granted ( 19,573 )

Shares cancelled/expired 3,731

Shares canceled/expired 2,888

Shares withheld for taxes 2,715

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The most recent automatic increase of 10.3 million shares occurre d o n February 1, 2024.

DocuSign, Inc.| 2024 10-K | 86

The majority of RSUs vest upon the satisfaction of a service-based vesting condition.

From time to time, we may also grant RSUs that are subject to either a performance-based or market-based vesting condition.

From time to time, we may also grant RSUs that are subject to either a performance-based or market-based vesting conditions.

The performance-based conditions will be satisfied upon satisfaction of certain financial performance targets.

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We expect to recognize this expense over the remaining weighted-average period of approximately 3.0 years.

As of January 31, 2023, the grant date fair value of unvested RSUs that are subject to market-based vesting conditions was $ 97.5 million.

As of January 31, 2024, the grant date fair value of unvested RSUs subject to market-based and performance-based vesting conditions was $ 117.9 million.

We calculated the fair value of the RSU with market conditions using Monte Carlo option-pricing model based on the following assumptions:

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Risk-free interest rate 4.12 % 3.21 % - 4.42 %

0.30 % 0.22 %

Expected dividend yield — % — % — %

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Expected volatility 71 % 54 % - 66 %

DocuSign, Inc.| 2023 Form 10-K | 86

Stock Options

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Outstanding at January 31, 2024, all vested and exercisable 1,385 $ 17.39 2.63 $ 60,117

DocuSign, Inc.| 2024 10-K | 87

As of January 31, 2024, there was no remaining unrecognized compensation cost related to stock option grants.

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1.15 % - 4.04 %

0.04 %- 0.06 %

Expected dividend yield — % — % — %

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In March 2022, our board of directors authorized a stock repurchase program of up to $ 200.0 million of our outstanding common stock.

During the year ended January 31, 2023, we repurchased and cancelled 1.1 million shares of common stock at an average price of $ 55.52 per share, for an aggregate amount of $ 63.0 million.

DocuSign, Inc.| 2023 Form 10-K | 87

Subsequently, in September 2023, our board of directors authorized an increase to its existing stock repurchase program for an additional amount of up to $ 300.0 million of our outstanding common stock.

During the year ended January 31, 2024, we repurchased and canceled 3.1 million shares of common stock at an average price of $ 47.57 per share, for an aggregate amount of $ 145.5 million.

During the year ended January 31, 2023, we repurchased and canceled 1.1 million shares of common stock at an average price of $ 55.52 per share, for an aggregate amount of $ 63.0 million.

DocuSign, Inc.| 2024 10-K | 88

Restructuring and Other Related Charges

2023 Restructuring Plan

During fiscal 2023, the board of directors authorized a restructuring plan (the “2023 Restructuring Plan”) in response to changing economic conditions and in an effort to reduce our operational costs and improve our organizational efficiency.

We expect to incur costs associated with the Restructuring Plan related to employee termination benefits and other costs mainly in the third and fourth quarters of fiscal 2023.

These amounts are recorded to the Restructuring and other related charges within our consolidated statements of operations and comprehensive loss as they are incurred.

As of the fourth quarter of fiscal 2023, the 2023 Restructuring Plan had been substantially completed.

2024 Restructuring Plan

During fiscal 2024 , the board of directors authorized a restructuring plan (the “2024 Restructuring Plan”) designed to support our growth, scale and profitability objectives.

As of the second quarter of fiscal 2024, the 2024 Restructuring Plan had been substantially completed.

The amounts associated with both restructuring plans are recorded to the Restructuring and other related charges within our consolidated statements of operations and comprehensive income (loss) as they are incurred.

For the year ended January 31, 2024, restructuring and other related charges were $ 30.4 million, and primarily composed of $ 28.8 million for employee termination benefits, which included stock-based compensation expense of $ 5.0 million.

For the year ended January 31, 2023, restructuring and other related charges were $ 28.3 million, and primarily composed of $ 27.4 million for employee termination benefits, which included stock-based compensation expense of $ 5.6 million.

The following table summarizes our restructuring liabilities during the year ended January 31, 2024:

(in thousands) January 31, 2023 Accruals Cash Payments January 31, 2024

2023 Restructuring Plan

Employee termination benefits $ 384 $ 1,749 $ ( 2,133 ) $ —

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Total $ 542 $ 1,769 $ ( 2,311 ) $ —

Net Loss per Share Attributable to Common Stockholders

The following table presents the calculation of basic and diluted net loss per share attributable to common stockholders for periods presented:

2024 Restructuring Plan

Employee termination benefits $ — $ 21,837 $ ( 21,837 ) $ —

Other — 1,554 ( 1,432 ) 122

Total $ — $ 23,391 $ ( 23,269 ) $ 122

DocuSign, Inc.| 2024 10-K | 89

Net Income (Loss) per Share Attributable to Common Stockholders

The following table presents the calculation of basic and diluted net income (loss) per share attributable to common stockholders for periods presented:

Year Ended January 31,

(in thousands, except per share data) 2024 2023 2022

Net loss attributable to common stockholders $ ( 97,454 ) $ ( 69,976 ) $ ( 243,267 )

Weighted-average common shares outstanding 200,903 196,675 185,760

Net loss per share attributable to common stockholders:

Basic and diluted $ ( 0.49 ) $ ( 0.36 ) $ ( 1.31 )

Net income (loss) attributable to common stockholders, basic $ 73,980 $ ( 97,454 ) $ ( 69,976 )

Interest expense on convertible senior notes 425 — —

Net income (loss) attributable to common stockholders, diluted $ 74,405 $ ( 97,454 ) $ ( 69,976 )

Weighted-average common shares outstanding, basic 204,070 200,903 196,675

Effect of dilutive securities 4,880 — —

Weighted-average common shares outstanding, diluted 208,950 200,903 196,675

Net income (loss) per share attributable to common stockholders:

Basic $ 0.36 $ ( 0.49 ) $ ( 0.36 )

Diluted $ 0.36 $ ( 0.49 ) $ ( 0.36 )

Outstanding potentially dilutive securities that were excluded from the diluted per share calculations because they would have been antidilutive are as follows:

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During the year ended January 31, 2024, 2023 and 2022, we recognized expenses of $ 33.2 million, $ 32.3 million and $ 25.5 million related to matching contributions.

DocuSign, Inc.| 2023 Form 10-K | 88

The domestic and foreign components of pre-tax loss were as follows:

The domestic and foreign components of pre-tax income (loss) were as follows:

Year Ended January 31,

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International 39,128 ( 109,554 ) 26,442

Loss before income taxes $ ( 89,881 ) $ ( 66,914 ) $ ( 229,492 )

The components of our income tax provision (benefit) were as follows:

Income (loss) before income taxes $ 93,679 $ ( 89,881 ) $ ( 66,914 )

DocuSign, Inc.| 2024 10-K | 90

The components of our income tax provision were as follows:

Year Ended January 31,

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Foreign tax rate differential 37.9 16.4 ( 3.4 )

Increase (decrease) unrecognized tax benefit ( 0.5 ) 1.0 ( 5.6 )

Foreign-derived intangible income deduction ( 11.7 ) — —

Stock-based compensation 81.8 ( 55.1 ) 309.6

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Effective tax rate 21.0 % ( 8.4 ) % ( 4.6 ) %

DocuSign, Inc.| 2023 Form 10-K | 89

DocuSign, Inc.| 2024 10-K | 91

The significant components of net deferred tax balances were as follows:

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in those jurisdictions in which we would incur significant additional costs upon repatriation of such amounts.

Therefore, no deferred tax liabilities for foreign withholding taxes have been recorded relating to the earnings of our foreign subsidiaries.

Recognized tax benefits on total stock-based compensation expense, which are reflected in the "Provision for income taxes" in the consolidated statements of operations and comprehensive loss, were $ 3.3 million, $ 1.6 million and $ 2.2 million in the years ended January 31, 2023, 2022 and 2021, respectively.

Our tax provision includes a $ 2.2 million tax shortfall, and $ 1.9 million and $ 2.0 million of excess tax benefits from stock-based compensation for the years ended January 31, 2023, 2022 and 2021, respectively.

We concluded any book/tax outside basis differences are not material to the consolidated financial statements as a whole as of and for the year ended January 31, 2024.

Recognized tax benefits on total stock-based compensation expense, which are reflected in the "Provision for income taxes" in the consolidated statements of operations and comprehensive income (loss), were $ 7.1 million, $ 3.3 million and $ 1.6 million in the years ended January 31, 2024, 2023 and 2022, respectively.

Our tax provision includes a $ 3.8 million tax shortfall, $ 2.2 million tax shortfall and $ 1.9 million of excess tax benefits from stock-based compensation for the years ended January 31, 2024, 2023 and 2022, respectively.

As of January 31, 2024, we had accumulated net operating loss carryforwards of $ 2.2 billion for federal and $ 1.2 billion for state.

3 unchanged sentences

As of January 31, 2024, we had accumulated U.S.

research tax credits of $ 126.3 million for federal, $ 33.3 million for California and $ 1.4 million for Illinois.

federal and Illinois research tax credits will begin to expire in 2033 and 2027, respectively.

research tax credits of $ 153.7 million for federal and $ 52.3 million for California.

federal research tax credits will begin to expire in 2033.

The California research tax credits do not expire.

5 unchanged sentences

Additional limitations on the use of these tax attributes could occur in the event of possible disputes arising in examination from various taxing authorities.

DocuSign, Inc.| 2023 Form 10-K | 90

DocuSign, Inc.| 2024 10-K | 92

A reconciliation of the beginning and ending balance of total unrecognized tax benefits was as follows:

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The remainder of the unrecognized tax benefits would not affect the effective tax rate due to a significant portion of the unrecognized tax benefit being recorded as a reduction in our gross deferred tax asset, offset by a reduction in our valuation allowance.

We have net uncertain tax positions of $ 11.3 million, $ 16.2 million and $ 16.7 million included in other liabilities on our consolidated balance sheet as of January 31, 2023, 2022 and 2021.

We have aggregate net uncertain tax positions of $ 12.3 million, $ 11.3 million and $ 16.2 million included in Other liabilities—noncurrent on our consolidated balance sheet as of January 31, 2024, 2023 and 2022.

We do not expect our gross unrecognized tax benefit to change significantly within the next 12 months.

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deferred tax assets have been fully offset by a valuation allowance.

The valuation allowance increased by $ 32.8 million in the year ended January 31, 2023 and by $ 275.4 million in the year ended January 31, 2022.

The valuation allowance decreased by $ 97.2 million in the year ended January 31, 2024 and increased by $ 32.8 million in the year ended January 31, 2023.

The following table represents the rollforward of our valuation allowance:

3 unchanged sentences

Valuation allowance charged to income tax provision ( 97,200 ) 32,825 256,017

Valuation allowance from acquisitions — — 9,354

Convertible senior notes settled — — 14,985

Convertible senior notes issued — — ( 15,453 )

Adoption of ASU 2020-06 — — 19,407

Ending balance $ 934,816 $ 1,032,016 $ 999,191

DocuSign, Inc.| 2023 Form 10-K | 91

Geographic Information

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had revenue greater than 10% of total revenue in the years ended January 31, 2024, 2023 and 2022.

DocuSign, Inc.| 2024 10-K | 93

Our long-lived assets by geographic area, which consist of property and equipment, net and operating lease right-of-use assets were as follows:

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Subsequent Events

On February 16, 2023, we announced a restructuring plan (“2024 Restructuring Plan”) that was designed to support our growth, scale and profitability objectives.

As part of the 2024 Restructuring Plan, we expect it will restructure and reduce our current workforce by approximately 10 %, primarily in our worldwide field organization.

We currently estimate that we will incur charges of approximately $ 25 million to $ 35 million in connection with the 2024 Restructuring Plan, consisting primarily of cash expenditures for employee transition, notice period severance payments, employee benefits, and related costs as well as non-cash expenses related to vesting of share-based awards.

On February 6, 2024, we announced a restructuring plan (“2025 Restructuring Plan”) that was designed to strengthen and support our financial and operational efficiency while continuing to invest in product and related initiatives.

As part of the 2025 Restructuring Plan, we expect to restructure and reduce our current workforce by approximately 6 %, with the majority in our Sales & Marketing organizations.

We currently estimate that we will incur charges of approximately $ 28 million to $ 32 million in connection with the 2025 Restructuring Plan, consisting primarily of cash expenditures for employee transition, notice period and severance payments, employee benefits, and related costs as well as non-cash expenses related to vesting of share-based awards.

We expect that the majority of the restructuring charges will be incurred in the first quarter of fiscal 2025, and that the execution of the 2025 Restructuring Plan will be substantially complete by the end of the second quarter of fiscal 2025.

On March 9, 2023, we announced that Cynthia Gaylor, our Chief Financial Officer, notified us of her intention to resign.

Gaylor will continue to provide services in her current capacities to provide for the orderly transition of her duties through June 15, 2023, the effective date of her resignation.

On March 10, 2023, the Federal Deposit Insurance Corporation (“FDIC”) issued a press release stating that Silicon Valley Bank, Santa Clara, California, (“SVB”) was closed by the California Department of Financial Protection and Innovation, which appointed the FDIC as receiver.

Thereafter, the FDIC transferred all deposits of SVB to a newly created bridge bank, named Silicon Valley Bridge Bank, N.A., providing all depositors access to their money beginning on March 13, 2023,and committing to the resolution of SVB in a manner that fully protects all depositors.

We maintain operating accounts at SVB with immaterial balances and therefore believe that our exposure to loss because of SVB’s receivership is immaterial.

CHANGES IN AND DISAGREEMENTS WITH ACCOUNTANTS ON ACCOUNTING AND FINANCIAL DISCLOSURE

DocuSign, Inc.| 2023 Form 10-K | 92

Compared sentence by sentence after normalising whitespace, quotation marks, case and digits, so re-formatting and restated figures do not read as changed language. Wording changes appear as one removal and one addition. The current filing and the prior one are authoritative.

What changed 10-K

Item 7A. Quantitative and Qualitative Disclosures About Market Risk