[Form 4] UPWORK, INC Insider Trading Activity

Rhea-AI Filing Summary

Upwork Inc. (UPWK) filed a Form 4 reporting equity transactions by its Chief Financial Officer. On 11/18/2025, 37,500 restricted stock units (RSUs) vested and were converted into the same number of common shares. These RSUs were part of an award that began vesting 25% on May 18, 2024, with additional vesting in equal quarterly installments.

To cover tax withholding obligations from this vesting, the CFO had 9,059 shares sold at a weighted average price of $16.1382 per share and 9,434 shares sold at a weighted average price of $17.2402 per share under a mandated “sell to cover” arrangement, which the filing states was not a discretionary trade. Following these transactions, the CFO directly owned 237,612 shares of Upwork common stock and held 225,000 RSUs representing contingent rights to receive an equal number of shares.

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 CA 94301

(City) (State) (Zip)

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

3. Date of Earliest Transaction (Month/Day/Year)
11/18/2025

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	11/18/2025		M		37,500	A	(1)	256,105	D
Common Stock	11/18/2025		S(2)		9,059	D	$16.1382(3)	247,046	D
Common Stock	11/18/2025		S(2)		9,434	D	$17.2402(4)	237,612	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)	11/18/2025		M			37,500	(5)	(5)	Common Stock	37,500	$0.00	225,000	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 $15.66 to $16.65 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 reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $16.67 to $17.4932 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.

5. The RSUs vest 25% on May 18, 2024 and then 1/16th of the total number of shares on each quarterly anniversary thereafter, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Remarks:

	/s/ Jacob McQuown, Attorney-in-Fact	11/20/2025
	** 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 transaction did UPWK report on this Form 4?

Upwork Inc. reported that its Chief Financial Officer had 37,500 restricted stock units vest and convert into common stock on 11/18/2025, along with related share sales to cover taxes.

How many UPWK shares were sold and at what prices on 11/18/2025?

The CFO had 9,059 shares sold at a weighted average price of $16.1382 per share and 9,434 shares sold at a weighted average price of $17.2402 per share, as disclosed in the Form 4.

Were the UPWK share sales discretionary trades by the CFO?

No. The filing explains the sales were made to cover tax withholding obligations tied to RSU vesting under a mandated “sell to cover” election in Upwork’s equity incentive plans and were not discretionary trades by the CFO.

How many UPWK shares does the CFO own after these transactions?

After the reported transactions, the CFO directly owned 237,612 shares of Upwork common stock, according to the Form 4.

How many restricted stock units does the UPWK CFO still hold?

The Form 4 states the CFO held 225,000 restricted stock units following the transactions, each RSU representing a contingent right to receive one share of Upwork common stock.

How do the UPWK CFO’s RSUs vest over time?

The RSU award vests 25% on May 18, 2024 and then 1/16th of the total shares on each quarterly anniversary thereafter, subject to the CFO’s continued employment with Upwork on each vesting date.