What changed in this filing

/stocks — the workspaceLOADING

Item 7A. Quantitative and Qualitative Disclosures About Market Risk

2023-03-27 compared with 2022-03-25 · 193 added, 187 removed, 1049 unchanged (27% of the section changed)

4 unchanged sentences

Interest Rate Risk

As of January 31, 2022, we had cash, cash equivalents and investments totaling $897.8 million, which consisted primarily of bank deposits, money market funds, commercial paper, corporate notes and bonds and U.S.

As of January 31, 2023, we had cash, cash equivalents and investments totaling $1.2 billion, which consisted primarily of bank deposits, money market funds, commercial paper, corporate notes and bonds and U.S.

Treasury and government agency securities.

4 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, 2022 as our 2023 Notes and 2024 Notes were issued at fixed rates of 0.5% and 0.0%, respectively.

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.

9 unchanged sentences

dollar against the other currencies may negatively or positively affect our operating results as expressed in U.S.

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

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.

19 unchanged sentences

Stockholders' Equity

Restructuring and Other Related Charges

Net Loss Per Share Attributable to Common Stockholders

11 unchanged sentences

Also in our opinion, the Company maintained, in all material respects, effective internal control over financial reporting as of January 31, 2023, based on criteria established in Internal Control - Integrated Framework (2013) issued by the COSO.

Changes in Accounting Principles

As discussed in Note 1 to the consolidated financial statements, the Company changed the manner in which it accounts for convertible debt effective February 1, 2021 and the manner in which it accounts for leases effective February 1, 2019.

Change in Accounting Principle

As discussed in Note 1 to the consolidated financial statements, the Company changed the manner in which it accounts for convertible debt effective February 1, 2021.

Basis for Opinions

38 unchanged sentences

/s/ PricewaterhouseCoopers LLP

San Francisco, California

San Jose, California

March 27, 2023

36 unchanged sentences

Commitments and contingencies (Note 10)

Convertible senior notes (Note 8) — 3,390

Stockholders’ equity

9 unchanged sentences

Additional paid-in capital 2,240,732 1,720,013

Accumulated other comprehensive income (loss) ( 4,809 ) 4,964

Accumulated other comprehensive loss ( 22,996 ) ( 4,809 )

Accumulated deficit ( 1,598,684 ) ( 1,438,189 )

19 unchanged sentences

General and administrative 316,228 232,757 192,697

Restructuring and other related charges 28,335 — —

Total operating expenses 2,067,858 1,702,646 1,262,844

10 unchanged sentences

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

Unrealized gains (losses) on investments, net of tax ( 1,838 ) ( 831 ) 865

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

Other comprehensive income (loss) ( 18,187 ) ( 9,773 ) 6,637

6 unchanged sentences

General and administrative 88,125 54,761 47,288

Restructuring and other related charges 5,626 — —

The accompanying notes are an integral part of these consolidated financial statements.

5 unchanged sentences

Balances at January 31, 2020 181,254 $ 18 $ 1,685,167 $ — $ ( 1,673 ) $ ( 1,137,185 ) $ 546,327

Settlement of convertible senior notes due in 2023 4,698 1 ( 31,933 ) — — — ( 31,932 )

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 2,072 — 24,305 — — — 24,305

Settlement of restricted stock units 4,072 — — — — — —

Tax withholding on net share settlement of restricted stock units — — ( 166,504 ) — — — ( 166,504 )

Tax withholding on net share settlement of restricted stock units and employee stock purchase plan — — ( 376,542 ) ( 1,048 ) — — ( 377,590 )

Employee stock purchase plan 464 — 29,859 — — — 29,859

1 unchanged sentence

Net loss — — — — — ( 243,267 ) ( 243,267 )

Cumulative impact of Topic 842 adoption — — — — — ( 48 ) ( 48 )

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

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

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

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

9 unchanged sentences

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

Settlement of restricted stock units and employee stock purchase plan 5,071 1 ( 1 ) — — — —

Settlement of restricted stock units 4,230 — — — — — —

Tax withholding on net share settlement of restricted stock units and employee stock purchase plan ( 1,428 ) — ( 88,900 ) ( 253 ) — — ( 89,153 )

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

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

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

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

22 unchanged sentences

Accounts receivable ( 75,964 ) ( 117,380 ) ( 73,913 )

Contract assets 4,893 1,912 ( 1,508 )

Prepaid expenses and other current assets ( 5,038 ) ( 7,074 ) ( 1,155 )

19 unchanged sentences

Repayments of convertible senior notes ( 16 ) ( 77,906 ) ( 384,199 )

Repurchases of common stock ( 63,041 ) — —

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

2 unchanged sentences

Proceeds from employee stock purchase plan 36,526 46,077 29,859

Net cash (used in) provided by financing activities ( 394,621 ) ( 58,976 ) ( 70,455 )

Net cash used in financing activities ( 98,256 ) ( 394,621 ) ( 58,976 )

Effect of foreign exchange on cash, cash equivalents and restricted cash ( 3,784 ) ( 5,594 ) 5,646

17 unchanged sentences

Fair value of shares issued as part of the repayments of convertible senior notes 2 174,230 1,233,990

Derecognition of build-to-suit lease — — 2,479

The accompanying notes are an integral part of these consolidated financial statements.

7 unchanged sentences

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

We provide a platform that enables businesses of all sizes to digitally prepare, sign, act on and manage agreements, thereby simplifying and accelerating the process of doing business.

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.

Basis of Presentation and Principles of Consolidation

14 unchanged sentences

• the fair value of certain stock awards issued;

• the f air value of the liability and equity components of convertible notes;

• the f air value of convertible notes;

• the useful life and recoverability of long-lived assets;

1 unchanged sentence

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

Since the emergence of the COVID-19 pandemic in March 2020, we have undertaken measures to protect our employees, partners and customers, including providing the majority of our employees the option to work remotely until at least January 31, 2023.

However, there can be no assurance that these measures will be effective, that we will be able to adopt new measures as needed or that we will be able to discontinue these measures without adversely affecting our business operations.

In addition, the COVID-19 pandemic and related recent developments (including the emergence of new coronavirus variants, the actions undertaken to contain the virus or mitigate its impacts, including actions mandated by governments and health authorities and changing public health directives or restrictions, vaccine efficacy against COVID-19 variants, current or future travel restrictions and how quickly and to what extent normal global economic and operating conditions can or will resume) have created and may continue to create significant uncertainty in global financial markets, which may decrease technology spending, depress demand for our products and harm our business and results of operations.

As of the date of issuance of the financial statements, we are not aware of any specific event or circumstance that would require us to update our estimates or judgments or revise the carrying value of our assets or liabilities, except for certain subleases that resulted in an impairment of $ 5.1 million on operating lease right-of-use assets recorded during the twelve months ended January 31, 2022.

These estimates may change as new events occur and additional information is obtained, which could be recognized in the consolidated financial statements as soon as they become known.

Actual results could differ from those estimates and any such differences may be material to our financial statements.

DocuSign, Inc.| 2022 Form 10-K | 69

Concentration of Credit Risk

11 unchanged sentences

To achieve the core principle of this standard, we apply the following steps:

DocuSign, Inc.| 2023 Form 10-K | 65

Identification of the contract, or contracts, with the customer

17 unchanged sentences

We generate all our revenue from contracts with customers.

DocuSign, Inc.| 2022 Form 10-K | 70

Subscription Revenue

12 unchanged sentences

The maintenance and support on the on-premises solutions is a stand-ready obligation to perform this service over the term of the arrangement and, as a result, is accounted for ratably over the term of the arrangement.

DocuSign, Inc.| 2023 Form 10-K | 66

Contracts with Multiple Performance Obligations

16 unchanged sentences

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

DocuSign, Inc.| 2022 Form 10-K | 71

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.

7 unchanged sentences

“Subscription” cost of revenue primarily consists of personnel and related costs to support our software platform, amortization expense associated with capitalized internally-developed software and technology-related intangible assets, property and equipment depreciation, allocated overhead expenses, merchant processing fees and server hosting costs.

DocuSign, Inc.| 2023 Form 10-K | 67

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

4 unchanged sentences

Stock-Based Compensation

Compensation cost for stock-based awards issued to employees, including stock options, employee stock purchase plan (“ESPP”) purchase rights and restricted stock units (“RSUs”), is measured at fair value on the date of grant and recognized over the service period, generally on a straight-line basis.

Compensation cost for stock-based awards issued to employees, including stock options, ESPP purchase rights and RSUs, is measured at fair value on the date of grant and recognized over the service period, generally on a straight-line basis.

The fair value of stock options and ESPP purchase rights is estimated on the date of grant using a Black-Scholes option-pricing model.

1 unchanged sentence

From time to time, we grant RSUs that also include performance-based or market-based conditions.

For RSUs granted with a market condition, we use a lattice model simulation analysis to value the RSUs.

Compensation expense for RSUs granted prior to January 31, 2018, is recognized on a graded basis over the requisite service period.

Such RSUs contain a performance condition in the form of a specified liquidity event which was satisfied upon the effectiveness of our registration statement on Form S-1 (“IPO Registration Statement”) on April 26, 2018.

RSUs granted after January 31, 2018, generally vest only on the satisfaction of service-based condition.

For RSUs granted with a market condition, we use a Monte Carlo option-pricing model to determine the fair value of the RSUs.

Compensation expense for RSUs granted with a market or a performance condition is recognized on a graded vesting basis over the requisite service period.

1 unchanged sentence

We recognize compensation expense related to shares issued pursuant to the 2018 ESPP on a straight-line basis over the offering period of six months .

DocuSign, Inc.| 2022 Form 10-K | 72

Compensation expense is recognized net of forfeitures that are estimated at the time of grant and revised in subsequent periods if actual forfeitures differ from those estimates.

2 unchanged sentences

In these instances, we record the liability for withholding amounts to be paid by us as treasury stock or as a reduction to additional paid-in capital, and include these payments as a reduction of cash flows from financing activities.

Restructuring charges

Restructuring liabilities arise when management commits to a restructuring plan, the restructuring plan identifies all significant actions, the period of time to complete the restructuring plan indicates that significant changes to the plan are not likely and employees who are impacted have been notified of the pending involuntary termination.

Restructuring charges are accrued in the period in which it is probable that the employees are entitled to the restructuring benefits and the amounts can be reasonably estimated.

We use the asset and liability method of accounting for income taxes.

2 unchanged sentences

We record a valuation allowance to reduce our deferred tax assets to an amount for which realization is more likely than not.

DocuSign, Inc.| 2023 Form 10-K | 68

Foreign Currency

21 unchanged sentences

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.

DocuSign, Inc.| 2022 Form 10-K | 73

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

5 unchanged sentences

Estimated credit losses are determined using a discounted cash flow model and recorded as an allowance, with changes in expected credit losses on our investments recorded in “Interest income and other income, net” in the consolidated statements of operations and comprehensive loss.

Unrealized gains and losses related to noncredit factors are reflected in “Accumulated other comprehensive income (loss)” on the consolidated balance sheets.

Prior to February 1, 2020, we evaluated our investments to assess whether those with unrealized loss positions were other than temporarily impaired.

We considered impairments to be other than temporary if they were related to deterioration in credit risk or if it is likely we will sell the securities before the recovery of their cost basis.

Realized gains and losses and declines in value judged to be other than temporary were determined based on the specific identification method and reported in “Interest income and other income, net” in the consolidated statements of operations and comprehensive loss.

Unrealized gains and losses related to noncredit factors are reflected in “Accumulated other comprehensive loss” on the consolidated balance sheets.

DocuSign, Inc.| 2023 Form 10-K | 69

Strategic Investments

3 unchanged sentences

An impairment loss is recorded when an event or circumstance indicates a decline in value has occurred.

As of January 31, 2022 and 2021, we held equity investments in privately-held companies totaling $ 12.4 million and $ 6.0 million that are classified in “Other assets—noncurrent” on our consolidated balance sheets.

As of January 31, 2023 and 2022, we held equity investments in privately-held companies totaling $ 12.5 million and $ 12.4 million that were classified in “Other assets—noncurrent” on our consolidated balance sheets.

Restricted Cash

6 unchanged sentences

Total cash, cash equivalents, and restricted cash $ 723,201 $ 509,679 $ 566,336

DocuSign, Inc.| 2022 Form 10-K | 74

Fair Value of Financial Instruments

13 unchanged sentences

The carrying values of cash, accounts receivable and accounts payable approximate their respective fair values due to the short period of time to maturity, receipt or payment.

Accounts Receivable and Allowance for Doubtful Accounts

DocuSign, Inc.| 2023 Form 10-K | 70

Accounts Receivable and Allowance for Doubtful Accounts and Credit Losses

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

3 unchanged sentences

Our allowance for doubtful accounts includes balances that are specifically identified for adequacy based on a regular evaluation of such factors as age of the receivable balance, current economic conditions, credit quality of the customer, and past collection experience.

We also include in our allowance for doubtful accounts an estimate for future credit losses, based on historical experience, which is recorded in the period in which we invoice our customers starting February 1, 2020.

We also include in our allowance for doubtful accounts an estimate for future credit losses, based on historical experience, which is recorded in the period in which we invoice our customers.

We do not have any off-balance-sheet credit exposure related to our customers.

11 unchanged sentences

Maintenance and repairs are expensed as incurred.

DocuSign, Inc.| 2022 Form 10-K | 75

On February 1, 2019, we adopted Accounting Standards Update (“ASU”) No.

2016-02, Leases (Topic 842) using the modified retrospective approach and applied the related optional practical expedients.

Leases arise from contractual obligations that convey the right to control the use of identified property, plant or equipment for a period of time in exchange for consideration.

11 unchanged sentences

Our leases include options to renew or terminate.

We include the option to renew or terminate in our determination of the lease term when the option is deemed to be reasonably assured to be exercised.

We include the option to renew or terminate in our determination of the lease term when the option is deemed to be reasonably certain to be exercised.

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.

DocuSign, Inc.| 2023 Form 10-K | 71

Goodwill represents the excess of the purchase price over the fair value of net assets acquired in business combinations accounted for using the acquisition method of accounting and is not amortized.

We test goodwill for impairment at least annually, in the fourth quarter of each year, or as events occur or circumstances change that would more likely than not reduce the fair value of a reporting unit below its carrying amount.

We test goodwill for impairment at least annually, on November 1, or as events occur or circumstances change that would more likely than not reduce the fair value of a reporting unit below its carrying amount.

Such events and changes may include:

3 unchanged sentences

For the purposes of impairment testing, we have determined that we have one operating segment and one reporting unit.

We performed qualitative assessment for the fiscal year ended January 31, 2022, and concluded that it is more likely than not that the fair value of the reporting unit significantly exceeds its carrying value.

We performed a qualitative assessment for the fiscal year ended January 31, 2023, and concluded that it is more likely than not that the fair value of the reporting unit significantly exceeds its carrying value.

There was no impairment of goodwill recorded in the years ended January 31, 2022 and 2021.

6 unchanged sentences

(1) Includes certifications, maintenance contracts and related relationships, subscription backlog and tradenames and trademarks

DocuSign, Inc.| 2022 Form 10-K | 76

We evaluate the estimated remaining useful lives of intangible assets and other long-lived assets to assess whether a revision to the remaining periods of amortization is required.

14 unchanged sentences

The excess of the fair value of purchase consideration over the values of these identifiable assets and liabilities is recorded as goodwill.

DocuSign, Inc.| 2023 Form 10-K | 72

Management’s estimates of fair value are based upon assumptions believed to be reasonable, but which are inherently uncertain.

12 unchanged sentences

The equity component was not remeasured as long as it continued to meet the conditions for equity classification.

DocuSign, Inc.| 2022 Form 10-K | 77

The transaction costs incurred related to the issuance of the convertible debt instruments were allocated to the liability and equity components based on their relative initial carrying value of the convertible debt instruments.

1 unchanged sentence

Effective February 1, 2021, we account for our convertible debt instruments as a single liability measured at its amortized cost.

See “Recently Adopted Accounting Pronouncements” below.

At issuance, the carrying amount is calculated as the proceeds, net of initial purchasers’ discounts and transaction costs.

9 unchanged sentences

Recently Adopted Accounting Pronouncements

On February 1, 2021, we early adopted ASU No.

2020-06, Debt—Debt with Conversion and Other Options (Subtopic 470-20) and Derivatives and Hedging—Contracts in Entity’s Own Equity (Subtopic 815-40) using the modified retrospective approach.

This ASU removes separation models for convertible debt with a cash conversion feature and convertible instruments with a beneficial conversion feature.

Such convertible debt is accounted for as a single liability measured at its amortized cost and convertible preferred stock will be accounted for as a single equity instrument measured at its historical cost, as long as no other features require bifurcation and recognition as derivatives.

The ASU also requires the if-converted method to be used for convertible instruments and the effect of potential share settlement be included in the diluted earnings per share calculation when an instrument may be settled in cash or shares.

The adoption of the ASU using the modified retrospective method resulted in:

• an increase of $ 77.3 million to the total carrying value of our convertible senior notes to reflect the full principal amount of the convertible notes outstanding net of issuance costs,

• reductions of $ 86.1 million to additional paid-in capital and $ 3.4 million to mezzanine equity to remove the equity component separately recorded for the conversion features associated with the convertible notes, and

• a cumulative-effect adjustment of $ 12.2 million to the beginning balance of accumulated deficit as of February 1, 2021.

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

DocuSign, Inc.| 2023 Form 10-K | 73

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.

2 unchanged sentences

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.

DocuSign, Inc.| 2022 Form 10-K | 78

Contract Balances

4 unchanged sentences

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

For the years ended January 31, 2022 , 2021 and 2020, we recognized revenue of $ 773.7 million , $ 499.5 million and $ 374.8 million that was included in the corresponding contract liability balance at the beginning of the periods presented.

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.

We receive payments from customers based upon contractual billing schedules.

12 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

6 unchanged sentences

Money market funds $ 110,716 $ — $ — $ 110,716

Cash equivalents (1)

Commercial paper 3,499 — — 3,499

Available-for-sale securities

1 unchanged sentence

Corporate notes and bonds 243,840 — ( 1,296 ) 242,544

government securities 58,050 12 ( 6 ) 58,056

governmental securities 20,036 — ( 76 ) 19,960

Level 2 total 393,746 1 ( 1,547 ) 392,200

Available-for-sale securities

Corporate notes and bonds 500 — — 500

Total $ 504,462 $ 1 $ ( 1,547 ) $ 502,916

2 unchanged sentences

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

The fair value of our Level 3 investments is determined based on an income approach using unobservable inputs.

The fair value of our available-for-sale securities as of January 31, 2023, by remaining contractual maturities, were as follows (in thousands):

5 unchanged sentences

Strategic Investments

During the year ended January 31, 2022, investments in equity securities without readily determinable fair values increased by $ 4.8 million due to adjustments related to observable price changes that occurred primarily during the three months ended April 30, 2021.

During the year ended January 31, 2021, there were no material observable price changes.

As of January 31, 2023 and 2022, we held equity investments in privately-held companies totaling $ 12.5 million and $ 12.4 million.

The carrying value of strategic investments is adjusted to fair value on a non-recurring basis for observable transactions of identical or similar investments of the same issuer or for impairment.

Strategic investments measured at fair value on a non-recurring basis are classified as Level 3 in the fair value hierarchy because nonrecurring fair value measurements may include observable and unobservable inputs.

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 quoted market prices in an inactive market on the last trading day of the reporting period (Level 2).

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.

26 unchanged sentences

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.

Prior to the acquisition, we held a $ 15.0 million minority investment in Seal’s outstanding stock.

As of the acquisition, the fair value of our minority interest, calculated as the difference between the total acquisition consideration and the portion attributable to third party Seal shareholders, approximated the carrying value.

Additionally, to certain continuing employees of Seal, we granted restricted stock units with service and performance conditions covering up to 0.1 million shares of our common stock with an aggregate grant date fair value of $ 11.4 million that will be accounted for as a post-acquisition compensation expense over the vesting period.

The performance-based condition was based on Seal meeting certain bookings targets for the year ended January 31, 2021 and that performance condition was not met.

DocuSign, Inc.| 2022 Form 10-K | 81

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

2 unchanged sentences

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.

The following table summarizes the acquisition date fair values of assets acquired and liabilities assumed at the date of acquisition:

(in thousands) As Adjusted

Cash and cash equivalents $ 729

Accounts receivable 9,654

Contract assets 5,813

Prepaid expense and other assets 4,829

Property and equipment 915

Goodwill 115,848

Intangible assets 83,700

Right-of-use Assets 3,130

Accounts payable ( 854 )

Accrued compensation ( 2,697 )

Contract liabilities ( 7,745 )

Accrued expenses and other liabilities ( 5,852 )

Lease liabilities ( 3,126 )

Deferred tax liability—noncurrent ( 3,891 )

$ 5.3 million of the goodwill recognized upon acquisition is deductible for U.K.

income tax purposes, where Seal is registered.

No amount of the goodwill recognized upon acquisition is deductible for U.S.

federal income tax purposes.

The estimated useful lives of intangible assets, primarily based on the expected period of benefit to us, and fair values of the identifiable intangible assets at acquisition date were as follows:

(in thousands, except years) Estimated Fair Value Weighted Average Useful Life

Existing technology $ 37,400 5 years

Customer relationships—subscription 41,700 10 years

Backlog—subscription 4,600 2 years

Total intangible assets $ 83,700 7.3 years

In the year ended January 31, 2021, we incurred acquisition costs of $ 6.2 million.

These costs included legal, accounting fees and other costs directly related to the acquisition of Seal and are recognized within operating expenses in our consolidated statements of operations.

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.

3 unchanged sentences

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:

DocuSign, Inc.| 2022 Form 10-K | 82

Year Ended January 31,

2 unchanged sentences

Net loss ( 246,819 )

Net loss per share attributable to common stockholders, basic and diluted $ ( 1.33 ) $ ( 1.49 )

Acquisition of Liveoak Technologies, Inc.

4 unchanged sentences

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 recorded approximately $ 39.9 million of goodwill which is primarily attributed to the assembled workforce and expanded market opportunities for integrating Liveoak’s technology with our existing product offering.

No goodwill recognized upon acquisition was deductible for U.S.

federal income tax purposes.

In the year ended January 31, 2021, we incurred costs of $ 1.8 million directly related to the acquisition of Liveoak.

These costs are recognized within operating expenses in our consolidated statements of operations.

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

4 unchanged sentences

Additions—Seal 1,185

Additions—Liveoak 39,892

Additions—Clause 4,100

Foreign currency translation ( 378 )

Balance at January 31, 2022 355,058

Additions—Seal 1,185

Additions—Clause 4,100

Foreign currency translation ( 1,439 )

37 unchanged sentences

Amortization of deferred contract fulfillment costs ( 50,081 ) ( 31,489 )

Cumulative translation adjustment ( 348 ) —

Ending balance $ 21,076 $ 19,088

32 unchanged sentences

• 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 January 31, 2022.

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 September 15, 2024.

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”):

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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 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.

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

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 the prior year, 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.

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.

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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.

We accounted for early conversions and settlements of the 2023 Notes during the year ended January 31, 2022 under ASU 2020-06.

Refer to Note 1 for further discussion of early adoption.

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.

As of January 31, 2022, we had not received conversion notices on our 2023 Notes.

DocuSign, Inc.| 2022 Form 10-K | 87

Net Carrying Amounts of the Liability and Equity Components

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.

(in thousands) 2023 2022

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Unpaid principal 37,083 37,099

unamortized debt discount — ( 15,116 )

unamortized transaction costs ( 118 ) ( 303 )

Net carrying value of current and noncurrent liability component $ 36,796 $ 98,660

Proceeds allocated to the conversion option (debt discount) $ 134,667

extinguishment or conversion ( 31,933 )

transaction costs ( 3,336 )

Net carrying value of mezzanine and permanent equity component $ 99,398

Net carrying value of liability component $ 36,965 $ 36,796

Excess of if-converted value over principal $ — $ 28,159

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Principal $ 690,000 $ 690,000

unamortized debt discount — ( 63,619 )

unamortized transaction costs ( 4,078 ) ( 8,309 )

Net carrying value of noncurrent liability component $ 681,691 $ 615,028

Proceeds allocated to the conversion option (debt discount) $ 64,453

transaction costs ( 1,185 )

Net carrying value of permanent equity component $ 63,268

Net carrying value of liability component $ 685,922 $ 681,691

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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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.

DocuSign, Inc.| 2022 Form 10-K | 88

The capped call transactions were as follows:

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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.

As of January 31, 2022 and January 31, 2021, 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 and January 31, 2021.

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

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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.

We lease offices under noncancelable operating lease agreements that expire at various dates through the end of February 2032.

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.

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

We include a renewal option in the lease terms for calculating our lease liability when we are reasonably certain that we will exercise the renewal option.

Operating lease expense for the fiscal years ended January 31, 2023 , 2022 and 2021 was $ 33.2 million, $ 34.4 million and $ 34.0 million.

DocuSign, Inc.| 2022 Form 10-K | 89

Future lease payments under noncancelable operating leases as of January 31, 2022, were as follows:

Future lease payments under operating leases as of January 31, 2023, were as follows:

Fiscal Period:

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The weighted average remaining lease terms as of January 31, 2023 and 2022 were 8.5 years and 5.7 years.

The discount rates for operating leases as of January 31, 2022 and 2021 were both 4.3 %.

The discount rates for operating leases as of January 31, 2023 and 2022 were 4.6 % and 4.3 %.

Commitments and Contingencies

As of January 31, 2022, we had unused letters of credit outstanding associated with our various operating leases totaling $ 7.3 million.

As of January 31, 2023, we had unused letters of credit outstanding totaling $ 5.3 million, the majority of which are associated with our various operating leases.

We have entered into certain noncancelable contractual arrangements that require future purchases of goods and services.

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Total $ 94,703

In May 2022, we entered into an agreement with a public cloud computing service provider.

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

Indemnification

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These agreements require us to indemnify such individuals, to the fullest extent permitted by Delaware law, for certain liabilities to which they may become subject as a result of their affiliation with us.

DocuSign, Inc.| 2022 Form 10-K | 90

Claims and Litigation

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DocuSign, Inc.

Securities Litigation

Securities Litigation and Related Derivative Litigation

On February 8, 2022, a putative securities class action was filed in the U.S.

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

The complaint 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.

The suit is purportedly brought on behalf of purchasers of our securities between June 4, 2020 and December 2, 2021.

We are not yet required to respond to the complaint, but believe it is devoid of merit.

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 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.

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).

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

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

Springer, et al., Case No.

1:22-cv-00652;

on May 19, 2022 in the U.S.

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

Springer, et al., Case No.

3:22-cv-02980;

on May 20, 2022, in the U.S.

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

Springer, et al., Case No.

3:22-cv-02987;

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

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

Springer, et al., Case No.

3:22-cv-05343.

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.

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.

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

By court order dated July 19, 2022, the two cases in the Northern District of California (Lapin and Votto) have been consolidated and stayed in light of the securities class action and no response to the complaints in the action will be due unless and until the stay is lifted.

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.

Springer, et al., Case No.

2022-0852-PAF.

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

DocuSign Civil Litigation

On October 25, 2022, an action was filed in the Delaware Court of Chancery, captioned Daniel D.

Mary Agnes Wilderotter and DocuSign, Inc., Civil Action No.

2022-0963-LWW, concerning Mr.

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.

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.

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

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

In addition, on January 26, 2023, Mr.

Springer delivered a demand for arbitration before JAMS, a private alternative dispute resolution firm, captioned Daniel D.

DocuSign, Inc.

and Mary Agnes Wilderotter.

In the demand, Mr.

Springer alleges that he was wrongfully terminated as CEO;

asserts related claims against DocuSign and Ms.

Wilderotter, including defamation, withholding promised compensation and breach of contract;

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.

Stockholders' Equity

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The 2018 Plan permits the granting of incentive stock options, nonstatutory stock options, stock appreciation rights, restricted stock awards, restricted stock unit awards, performance stock awards, performance cash awards and other stock awards.

RSUs granted under the 2018 Plan generally vest over a four-year period, either quarterly or with 25 %

DocuSign, Inc.| 2022 Form 10-K | 91

vesting at the end of one year and the remainder quarterly thereafter.

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

Shares available for grant under the 2018 Plan for the year ended January 31, 2023 was as follows:

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The most recent automatic increase of 10.1 million shares occurre d o n February 1, 2023.

The majority of RSUs granted after January 31, 2018 vest upon the satisfaction of a service-based vesting condition.

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.

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Unvested at January 31, 2023 17,621 $ 81.30

As of January 31, 2022, our total unrecognized compensation cost related to RSUs was $ 875.8 million.

As of January 31, 2023, our total unrecognized compensation cost related to RSUs was $ 1.0 billion.

We expect to recognize this expense over the remaining weighted-average period of approximately 3.1 years.

We have $ 55.7 million and $ 46.2 million of unvested RSUs that are subject to market-based vesting conditions as of January 31, 2022 and 2021.

We calculated the fair value of the RSU with market conditions using lattice model simulation analysis based on the following assumptions:

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.

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

Year Ended January 31,

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Risk-free interest rate 3.21 % - 4.42 %

0.30 % 0.22 %

Expected dividend yield — % — % — %

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Expected volatility 54 % - 66 %

Weighted-average grant date fair value per share $ 331.26 $ 206.54 $ 45.14

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

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(in thousands, except per share data and years) Number of Options Weighted-Average Exercise Price Per Share Weighted-Average Remaining Contractual Term (Years) Aggregate Intrinsic Value

Outstanding at January 31, 2021 4,798 $ 15.55 5.03 $ 1,042,879

Issued as consideration for acquisition — —

Outstanding at January 31, 2022, all vested and exercisable 3,105 $ 16.41 4.45 $ 339,286

Exercised ( 868 ) 14.60

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The aggregate intrinsic value of options exercised during the years ended January 31, 2023, 2022 and 2021 was $ 48.1 million, $ 391.2 million and $ 302.4 million.

The total grant date fair value of options vested during the years ended January 31, 2022, 2021 and 2020 was $ 0.3 million, $ 7.5 million and $ 10.5 million.

2018 Employee Stock Purchase Plan

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Expected volatility 83 % - 102 %

Weighted-average grant date fair value per share $ 205.71 - $ 265.12

$ 90.15 - $ 221.20

$ 14.88 - $ 18.56

The expected term for the ESPP purchase rights is based on the duration of the offering period.

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As of January 31, 2023, 9.4 million shares of common stock were reserved for issuance under the ESPP.

Stock Repurchase Program

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

Restructuring and Other Related Charges

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.

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, 2023:

(in thousands) January 31, 2022 Accruals Cash Payments January 31, 2023

Employee termination benefits $ — $ 21,748 $ ( 21,364 ) $ 384

Other — 1,058 ( 900 ) 158

Total $ — $ 22,806 $ ( 22,264 ) $ 542

Net Loss per Share Attributable to Common Stockholders

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During the year ended January 31, 2023, 2022 and 2021, we recognized expenses of $ 32.3 million, $ 25.5 million and $ 18.9 million related to matching contributions.

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

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

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

DocuSign, Inc.| 2022 Form 10-K | 94

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

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(in percentage) 2023 2022 2021

U.S statutory rate 21.0 % 21.0 % 21.0 %

statutory rate 21.0 % 21.0 % 21.0 %

State taxes ( 2.4 ) 2.1 2.7

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Change in valuation allowance ( 35.5 ) ( 386.4 ) ( 118.4 )

Dual Jurisdiction Deferred Taxes 39.2 — —

Research and development credits 20.1 58.2 9.1

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Stock-based compensation 49,615 35,319

Operating lease liability 29,644 36,148

Research and development credits 118,183 99,353

Capitalized research and development expenses 204,501 —

Other 55,087 57,049

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Deferred tax liabilities

Operating lease right-of-use asset ( 21,038 ) ( 27,654 )

Deferred contract acquisition costs ( 103,185 ) ( 74,727 )

Convertible debt — ( 18,854 )

Acquired intangibles ( 1,006 ) ( 11,939 )

Other ( 30,646 ) ( 31,765 )

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

In the years ended January 31, 2022, 2021 and 2020, total stock-based compensation expense was $ 408.5 million, $ 286.9 million and $ 206.4 million.

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 $ 1.6 million, $ 2.2 million and $ 1.0 million in the years ended January 31, 2022, 2021 and 2020.

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.

As of January 31, 2023, we had accumulated net operating loss carryforwards of $ 2.9 billion for federal and $ 1.4 billion for state.

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As of January 31, 2023, we had accumulated U.S.

research tax credits of $ 108.5 million for federal and $ 26.8 million for state.

federal research tax credits will begin to expire in 2033.

state research tax credits do not expire.

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.

The California research tax credits do not expire.

Available net operating losses may be subject to annual limitations due to ownership change limitations provided by the Internal Revenue Code, as amended (the "Code"), and similar state provisions.

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Gross decrease for tax positions of prior years ( 1,734 ) ( 1,513 )

Settlements ( 2,484 ) —

Gross increase for tax positions of current year 5,102 9,176

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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.

A significant portion of the unrecognized tax benefit was recorded as a reduction in our gross deferred tax assets, 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.

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As of January 31, 2023, accrued interest and penalties was $ 0.6 million.

Our tax years from inception in 2003 through January 31, 2022, remain subject to examination by the U.S.

and California, as well as various other jurisdictions.

We are under examination by the Israeli Tax Authorities for the period January 1, 2016 through January 31, 2021.

The Company believes that it has reserved adequate amounts for these jurisdictions.

We are subject to taxation in the U.S.

and various foreign jurisdictions.

Our tax years from inception in 2003 through January 31, 2023 remain subject to examination by U.S.

and California taxing authorities, as well as taxing authorities in various other state and foreign jurisdictions.

We are not under examination in any material jurisdictions.

We recognize valuation allowances on deferred tax assets if it is more likely than not that some or all the deferred tax assets will not be realized.

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Subsequent Events

In March 2022, our Board of Directors authorized a stock repurchase program of up to $ 200 million of our outstanding common stock.

The program has no minimum purchase commitment and no mandated end date.

The repurchase program may be suspended or discontinued at any time at our discretion.

The timing and the amount of any repurchased common stock will be determined by management based on its evaluation of market conditions and other factors.

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.

We expect that the majority of the restructuring charges will be incurred in the first quarter of fiscal 2024 and that the execution of the 2024 Restructuring Plan will be substantially complete by the end of the second quarter of fiscal 2024.

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