James P. Shaughnessy - 15 Jun 2025 Form 4 Insider Report for DOCUSIGN, INC. (DOCU)

Role: Chief Legal Officer
Signature: /s/ Lisa Yun, Attorney-in-fact
Issuer symbol: DOCU
Transactions as of: 15 Jun 2025
Net transactions value: $0
Form type: 4
Filing time: 17 Jun 2025, 18:03:34 UTC
Previous filing: 02 Apr 2025
Next filing: 02 Jul 2025
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
Shaughnessy James P	Chief Legal Officer	C/O DOCUSIGN, INC., 221 MAIN STREET, SUITE 1550, SAN FRANCISCO	/s/ Lisa Yun, Attorney-in-fact	17 Jun 2025	0001294600

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	DOCU	Common Stock	Options Exercise	$0	+25,418	+55%	$0.000000	71,293	15 Jun 2025	Direct
transaction	DOCU	Common Stock	Tax liability	$0	-11,976	-17%	$0.000000	59,317	15 Jun 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	-4,392	-20%	$0.000000	17,565	15 Jun 2025	Common Stock	4,392		Direct	F2, F3, F4
transaction	DOCU	Restricted Stock Units	Options Exercise	$0	-2,932	-17%	$0.000000	14,658	15 Jun 2025	Common Stock	2,932		Direct	F2, F4, F5
transaction	DOCU	Restricted Stock Units	Options Exercise	$0	-2,187	-11%	$0.000000	17,498	15 Jun 2025	Common Stock	2,187		Direct	F2, F4, F6
transaction	DOCU	Restricted Stock Units	Options Exercise	$0	-3,370	-7.7%	$0.000000	40,442	15 Jun 2025	Common Stock	3,370		Direct	F2, F4, F7
transaction	DOCU	Performance Stock Units	Options Exercise	$0	-536	-20%	$0.000000	2,142	15 Jun 2025	Common Stock	536		Direct	F8, F9
transaction	DOCU	Performance Stock Units	Options Exercise	$0	-1,458	-20%	$0.000000	5,834	15 Jun 2025	Common Stock	1,458		Direct	F8, F10
transaction	DOCU	Performance Stock Units	Options Exercise	$0	-4,367	-32%	$0.000000	9,113	15 Jun 2025	Common Stock	4,367		Direct	F8, F11
transaction	DOCU	Performance Stock Units	Options Exercise	$0	-6,176	-46%	$0.000000	7,304	15 Jun 2025	Common Stock	6,176		Direct	F8, F12

* 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") or performance-vested restricted stock units ("PSUs").
F2	Each RSU represents a contingent right to receive one share of the Issuer's common stock.
F3	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.
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 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.
F6	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.
F7	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.
F8	Each PSU represents a contingent right to receive one share of the Issuer's common stock.
F9	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.
F10	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.
F11	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.
F12	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.