[Form 4] DOCUSIGN, INC. Insider Trading Activity

Rhea-AI Filing Summary

DocuSign CFO Blake Grayson reported multiple equity transactions on 09/15/2025, primarily reflecting the vesting and settlement of restricted stock units (RSUs) and performance stock units (PSUs). The filing shows 37,449 shares acquired and 15,289 shares withheld to satisfy tax obligations, leaving the reporting person with 136,958 shares after the transactions. Several RSU grants vest over multi‑year schedules (quarterly over four years or front‑loaded schedules) and PSUs vest subject to FY25 subscription revenue and free cash flow performance with a 200% maximum payout, with earned PSUs vesting partially after one year then in quarterly installments. All reported holdings are direct.

Positive

• 37,449 shares acquired through settlement of RSUs/PSUs, increasing direct ownership
• Performance stock units are tied to FY25 subscription revenue and free cash flow with up to 200% payout, aligning executive incentives with company performance
• Detailed vesting schedules disclosed, showing multi‑year retention incentives

Negative

• 15,289 shares withheld to satisfy tax obligations, reducing net shares received from vesting
• Potential dilution from vested and potentially vested PSUs if performance targets are achieved up to the 200% cap

Insights

Securities Analyst

TL;DR: Routine executive equity vesting and tax withholdings; not a material change to ownership.

This Form 4 documents scheduled vesting and settlement activity for the company's CFO rather than open-market purchases or sales. The filing records 37,449 shares acquired from vested RSUs/PSUs and 15,289 shares withheld for taxes, resulting in 136,958 shares beneficially owned. The PSUs are performance‑based tied to FY25 subscription revenue and free cash flow with a 200% cap, which could affect future dilution if targets are met. Timing and structure are consistent with standard executive compensation practices and do not indicate an opportunistic trade.

Corporate Governance Expert

TL;DR: Compensation-driven vesting with performance conditions; disclosure aligns with typical Section 16 reporting.

The filing discloses multiple RSU schedules (quarterly vesting over four years or graduated year‑by‑year vesting) and PSUs contingent on FY25 metrics. Shares withheld to cover tax obligations are explicitly noted, a common settlement method. All holdings are reported as direct ownership and the form is signed by an attorney‑in‑fact, indicating administrative handling. There are no indications of departures, option exercises, sales to raise cash, or other governance red flags in this submission.

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^*

GRAYSON BLAKE JEFFREY

(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 Financial 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		37,449	A	$0	136,958	D
Common Stock	09/15/2025		F		15,289(1)	D	$0	121,669	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			23,141	(3)	(4)	Common Stock	23,141	$0	161,988	D
Restricted Stock Units	(2)	09/15/2025		M			5,119	(5)	(4)	Common Stock	5,119	$0	56,312	D
Restricted Stock Units	(2)	09/15/2025		M			5,185	(6)	(4)	Common Stock	5,185	$0	46,670	D
Performance Stock Units	(7)	09/15/2025		M			1,659	(8)	(8)	Common Stock	1,659	$0	12,184	D
Performance Stock Units	(7)	09/15/2025		M			2,345	(9)	(9)	Common Stock	2,345	$0	8,749	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") and performance-vested restricted stock unit ("PSUs").

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

3. The RSUs will vest in sixteen equal quarterly installments over four years, with a vesting commencement date of June 10, 2023, in each case subject to the Reporting Person being a service provider through each such date. The RSUs 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 May 10, 2024, in each case subject to the reporting person being a service provider through such date.

6. 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.

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

8. 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.

9. 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	09/16/2025
	** 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.
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FAQ

What transactions did DOCU insider Blake Grayson report on 09/15/2025?

The Form 4 reports 37,449 shares acquired from RSU/PSU settlement and 15,289 shares withheld for taxes, resulting in 136,958 shares beneficially owned.

Why were shares withheld in the DOCU Form 4 filing?

The filing states shares were withheld to satisfy a tax obligation realized upon vesting and settlement of RSUs and PSUs.

What performance metrics govern the PSUs reported in the DOCU filing?

PSUs vest based on the company's FY25 subscription revenue and FY25 free cash flow, each with a maximum payout capped at 200% of target.

How are the RSUs scheduled to vest according to the Form 4?

RSU schedules include quarterly vesting over four years, some grants with a commencement date in 2023, 2024, or 2025, and one grant with front‑loaded year percentages (40%/35%/15%/10%).

Does the Form 4 indicate direct or indirect ownership for Blake Grayson?

All reported holdings in the Form 4 are listed as direct (D) beneficial ownership.