[Form 4] DOCUSIGN, INC. Insider Trading Activity

Rhea-AI Filing Summary

James P. Shaughnessy, Chief Legal Officer of DocuSign (DOCU), reported insider transactions dated 09/15/2025. The filing shows 20,966 shares were acquired and 9,841 shares were withheld to satisfy tax obligations, leaving the reporting person with 62,942 total shares after the non-derivative transactions. The Form 4 details multiple restricted stock units (RSUs) and performance stock units (PSUs) that vested or were settled on that date, with specified vesting schedules and performance conditions tied to subscription revenue and free cash flow for FY24 and FY25.

Positive

• Executive ownership increased through settlement of 20,966 shares, which can align management and shareholder interests
• Performance-based PSUs tie a portion of compensation to subscription revenue and free cash flow, capped at 200% of target

Negative

• 9,841 shares were withheld to satisfy tax obligations, reducing the net increase in outstanding shares held by the reporting person
• No open-market purchases were reported; the changes reflect internal equity settlements rather than fresh insider purchases

Insights

Securities Analyst

TL;DR: Routine executive vesting and tax-withholding transactions; no new cash purchases or sales reported.

The Form 4 documents settlement of vested equity awards for the Chief Legal Officer, including RSUs and PSUs, and the issuer withholding shares to satisfy tax liabilities. Transaction codes indicate vesting/settlement activity rather than open-market trades. The PSUs have performance-based vesting tied to subscription revenue and free cash flow for FY24 and FY25, each capped at 200% of target, which is material for executive compensation alignment but does not, by itself, change public capital structure.

Corporate Governance Expert

TL;DR: Settlement of long-term incentive awards with standard vesting schedules and tax withholding; governance implications are routine.

The filing lists multiple RSU grant tranches with staggered vesting commencement dates (June 10, 2022; July 10, 2022; May 10, 2023; May 10, 2024; May 10, 2025) and PSUs tied to specific FY performance periods. The RSUs include accelerated vesting upon certain terminations or change in control. These terms align executive incentives with multi-year performance metrics and retention, reflecting standard governance practice for senior officers.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

1. Name and Address of Reporting Person^*

Shaughnessy James P

(Last) (First) (Middle)

C/O DOCUSIGN, INC.

221 MAIN STREET, SUITE 800

(Street)

SAN FRANCISCO CA 94105

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
DOCUSIGN, INC. [ DOCU ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Legal Officer

3. Date of Earliest Transaction (Month/Day/Year)
09/15/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	09/15/2025		M		20,966	A	$0	72,783	D
Common Stock	09/15/2025		F		9,841(1)	D	$0	62,942	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Restricted Stock Units	(2)	09/15/2025		M			4,391	(3)	(4)	Common Stock	4,391	$0	13,174	D
Restricted Stock Units	(2)	09/15/2025		M			2,931	(5)	(4)	Common Stock	2,931	$0	11,727	D
Restricted Stock Units	(2)	09/15/2025		M			2,187	(6)	(4)	Common Stock	2,187	$0	15,311	D
Restricted Stock Units	(2)	09/15/2025		M			3,370	(7)	(4)	Common Stock	3,370	$0	37,072	D
Restricted Stock Units	(2)	09/15/2025		M			3,457	(8)	(4)	Common Stock	3,457	$0	31,113	D
Performance Stock Units	(9)	09/15/2025		M			536	(10)	(10)	Common Stock	536	$0	1,606	D
Performance Stock Units	(9)	09/15/2025		M			1,458	(11)	(11)	Common Stock	1,458	$0	4,376	D
Performance Stock Units	(9)	09/15/2025		M			1,092	(12)	(12)	Common Stock	1,092	$0	8,021	D
Performance Stock Units	(9)	09/15/2025		M			1,544	(13)	(13)	Common Stock	1,544	$0	5,760	D

Explanation of Responses:

1. Represents shares withheld by the Issuer to satisfy a tax obligation realized by the Reporting Person upon the vesting and settlement of restricted stock units ("RSUs") or performance-vested restricted stock units ("PSUs").

2. Each RSU represents a contingent right to receive one share of the Issuer's common stock.

3. The RSUs will vest 35% on the one year anniversary of the grant date, 35% in equal quarterly installments after year one, 15% in equal quarterly installments after year two, and 15% in equal quarterly installments after year 3, with a vesting commencement date of June 10, 2022, in each case subject to the Reporting Person being a service provider through each such date. The restricted stock units are subject to accelerated vesting in the event of a termination of employment of the Reporting Person including under certain circumstances following a change in control of the Issuer.

4. The RSUs do not expire; they either vest or are canceled prior to vesting date.

5. The RSUs will vest in equal quarterly installments over four years, with a vesting commencement date of July 10, 2022, in each case subject to the Reporting Person being a service provider through each such date. The restricted stock units are subject to accelerated vesting in the event of a termination of employment of the Reporting Person including under certain circumstances following a change in control of the Issuer.

6. The RSUs will vest in equal quarterly installments over four years, with a vesting commencement date of May 10, 2023, in each case subject to the reporting person being a service provider through such date.

7. The RSUs will vest in equal quarterly installments over four years, with a vesting commencement date of May 10, 2024, in each case subject to the reporting person being a service provider through such date.

8. The RSUs will vest quarterly over a four year period commencing May 10, 2025, with 40% vesting during year 1, 35% vesting during year 2, 15% vesting during year 3, and 10% vesting during year 4, in each case subject to the Reporting Person being a service provider through each such date.

9. Each PSU represents a contingent right to receive one share of the Issuer's common stock.

10. The PSUs will vest depending on the Company's subscription revenue for the twelve-month period ended January 31, 2024 (the "FY24 Performance Period"). The maximum number of the subscription revenue-based PSUs that may vest is capped at 200% of the target number of subscription revenue-based PSUs. To the extent achieved, 1/3 of any achieved subscription revenue-based PSUs will vest following the one-year anniversary of the date of grant and the balance will vest in eight equal quarterly installments thereafter, subject to continued service with certain limited exceptions.

11. The PSUs will vest depending on the Company's free cash flow for the FY24 Performance Period. The maximum number of free cash flow-based PSUs that may vest is capped at 200% of the target number of free cash flow-based PSUs. To the extent achieved, 1/3 of any achieved free cash flow-based PSUs will vest following the one-year anniversary of the date of grant and the balance will vest in eight equal quarterly installments thereafter subject to continued service with certain limited exceptions.

12. The PSUs will vest depending on the Company's subscription revenue for the twelve-month period ended January 31, 2025 (the "FY25 Performance Period"). The maximum number of subscription revenue-based PSUs that may vest is capped at 200% of the target number of subscription revenue-based PSUs. To the extent achieved, 1/3 of any achieved subscription revenue-based PSUs will vest following the one-year anniversary of the date of grant and the balance will vest in eight equal quarterly installments thereafter, subject to continued service with certain limited exceptions.

13. The PSUs will vest depending on the Company's free cash flow for the FY25 Performance Period. The maximum number of free cash flow-based PSUs that may vest is capped at 200% of the target number of free cash flow-based PSUs. To the extent achieved, 1/3 of any achieved free cash flow-based PSUs will vest following the one-year anniversary of the date of grant and the balance will vest in eight equal quarterly installments thereafter, subject to continued service with certain limited exceptions.

Remarks:

	/s/ Derrick Chapman, Attorney-in-fact	09/17/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What insider transactions did DOCU Chief Legal Officer report on 09/15/2025?

The filing reports the settlement of vested awards resulting in 20,966 shares acquired and 9,841 shares withheld for taxes on 09/15/2025.

How many DOCU shares does James P. Shaughnessy beneficially own after the transactions?

Following the reported transactions, the Form 4 shows 62,942 shares beneficially owned for the reporting person from the non-derivative portion.

What types of equity awards were involved in the DOCU Form 4?

The Form 4 lists Restricted Stock Units (RSUs) and Performance Stock Units (PSUs) that vested or were settled on 09/15/2025.

What performance metrics govern the PSUs in this filing?

PSU vesting depends on the Company's subscription revenue and free cash flow for the FY24 and FY25 performance periods, each capped at 200% of target.

Do the RSUs have accelerated vesting conditions?

Yes, the RSUs are subject to accelerated vesting upon certain terminations of employment, including certain circumstances following a change in control.