Blake Jeffrey Grayson - 15 Sep 2025 Form 4 Insider Report for DOCUSIGN, INC. (DOCU)

Role: Chief Financial Officer
Signature: /s/ Derrick Chapman, Attorney-in-fact
Issuer symbol: DOCU
Transactions as of: 15 Sep 2025
Net transactions value: $0
Form type: 4
Filing time: 16 Sep 2025, 19:05:34 UTC
Previous filing: 17 Jul 2025
Next filing: 17 Sep 2025
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
GRAYSON BLAKE JEFFREY	Chief Financial Officer	C/O DOCUSIGN, INC., 221 MAIN STREET, SUITE 800, SAN FRANCISCO	/s/ Derrick Chapman, Attorney-in-fact	16 Sep 2025	0001796825

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	DOCU	Common Stock	Options Exercise	$0	+37,449	+38%	$0.000000	136,958	15 Sep 2025	Direct
transaction	DOCU	Common Stock	Tax liability	$0	-15,289	-11%	$0.000000	121,669	15 Sep 2025	Direct	F1

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	DOCU	Restricted Stock Units	Options Exercise	$0	-23,141	-12%	$0.000000	161,988	15 Sep 2025	Common Stock	23,141		Direct	F2, F3, F4
transaction	DOCU	Restricted Stock Units	Options Exercise	$0	-5,119	-8.3%	$0.000000	56,312	15 Sep 2025	Common Stock	5,119		Direct	F2, F4, F5
transaction	DOCU	Restricted Stock Units	Options Exercise	$0	-5,185	-10%	$0.000000	46,670	15 Sep 2025	Common Stock	5,185		Direct	F2, F4, F6
transaction	DOCU	Performance Stock Units	Options Exercise	$0	-1,659	-12%	$0.000000	12,184	15 Sep 2025	Common Stock	1,659		Direct	F7, F8
transaction	DOCU	Performance Stock Units	Options Exercise	$0	-2,345	-21%	$0.000000	8,749	15 Sep 2025	Common Stock	2,345		Direct	F7, F9

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	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").
F2	Each RSU represents a contingent right to receive one share of the Issuer's common stock.
F3	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
F4	The RSUs do not expire; they either vest or are canceled prior to vesting date.
F5	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.
F6	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.
F7	Each PSU represents a contingent right to receive one share of the Issuer's common stock.
F8	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.
F9	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.