Upwork (NASDAQ: UPWK) CFO exercises RSUs and sells 9,278 shares to cover taxes

Rhea-AI Filing Summary

Upwork, Inc. Chief Financial Officer Erica Gessert reported routine equity compensation activity involving restricted stock units and common stock. On March 18, 2026, she exercised restricted stock units covering 8,433 and 9,699 shares, receiving the same number of common shares at a conversion price of $0.00 per share.

On the same date, 9,278 shares of common stock were sold at a weighted average price of $12.312 per share, pursuant to a mandatory “sell to cover” arrangement to satisfy tax withholding obligations, as required under Upwork’s equity incentive plans. Following these transactions, Gessert directly held 307,240 shares of common stock. The restricted stock units vest in equal quarterly installments over four years beginning on June 18, 2024 and June 18, 2025, subject to her continued employment.

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).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Gessert Erica

(Last) (First) (Middle)

C/O UPWORK INC.

530 LYTTON AVENUE, SUITE 301

(Street)

PALO ALTO CALIFORNIA 94301

(City) (State) (Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
UPWORK, INC [ UPWK ]

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
03/18/2026

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

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

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

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	03/18/2026		M		8,433	A	(1)	306,819	D
Common Stock	03/18/2026		M		9,699	A	(1)	316,518	D
Common Stock	03/18/2026		S(2)		9,278	D	$12.312(3)	307,240	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	(1)	03/18/2026		M			8,433	(4)	(4)	Common Stock	8,433	$0.00	67,463	D
Restricted Stock Units	(1)	03/18/2026		M			9,699	(5)	(5)	Common Stock	9,699	$0.00	116,397	D

Explanation of Responses:

1. Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.

2. Represents the number of shares required to be sold by the Reporting Person to cover tax withholding obligations in connection with the vesting of the RSUs listed in Table II. This sale is mandated by the Issuer's election under its equity incentive plans to require the satisfaction of tax withholding obligations to be funded by a "sell to cover" transaction and does not represent a discretionary trade by the Reporting Person.

3. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $12.13 to $12.52 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon written request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

4. The RSUs vest in equal quarterly installments over four years beginning on June 18, 2024, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

5. The RSUs vest in equal quarterly installments over four years beginning on June 18, 2025, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Remarks:

	/s/ Jacob McQuown, Attorney-in-Fact	03/20/2026
	** 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.
* Form 4: SEC 1474 (03-26)

FAQ

What insider transactions did Upwork (UPWK) CFO Erica Gessert report on March 18, 2026?

Upwork CFO Erica Gessert exercised restricted stock units into 8,433 and 9,699 shares of common stock and reported a related sale of 9,278 shares. The sale was linked to tax withholding obligations rather than a discretionary trading decision.

How many Upwork (UPWK) shares does CFO Erica Gessert hold after the latest Form 4?

After the March 18, 2026 transactions, Erica Gessert directly holds 307,240 shares of Upwork common stock. This reflects her equity position following RSU conversions and the mandated sale of 9,278 shares to cover associated tax withholding obligations.

Was the Upwork (UPWK) CFO’s March 18, 2026 share sale a discretionary trade?

The 9,278-share sale was not discretionary. It was a “sell to cover” transaction mandated by Upwork’s equity incentive plans to fund tax withholding obligations arising from RSU vesting, according to the Form 4 explanatory footnote.

At what price were the 9,278 Upwork (UPWK) shares sold by the CFO on March 18, 2026?

The 9,278 shares were sold at a weighted average price of $12.312 per share. The filing states individual sale prices ranged from $12.13 to $12.52 per share, and detailed breakdowns are available on request from the reporting person.

How do Erica Gessert’s Upwork (UPWK) RSUs vest following the reported Form 4?

The restricted stock units vest in equal quarterly installments over four years. One RSU grant began vesting on June 18, 2024, and another begins on June 18, 2025, with each vesting schedule conditioned on her continued employment at Upwork.

What type of derivative security did the Upwork (UPWK) CFO exercise in the March 18, 2026 Form 4?

Erica Gessert exercised restricted stock units, each representing a contingent right to receive one share of Upwork common stock. The Form 4 shows two RSU exercises, converting 8,433 and 9,699 units into the same number of common shares at a $0.00 conversion price.