Upwork CFO reports RSU vesting and tax share sale

Upwork, Inc.’s Chief Financial Officer Erica Gessert reported multiple equity-related transactions.

Rhea-AI Filing Summary

Upwork, Inc.’s Chief Financial Officer Erica Gessert reported multiple equity-related transactions. On February 17–18, 2026, performance stock units and restricted stock units converted into common stock, and she also received a new grant of 136,388 RSUs that vest quarterly over four years beginning May 18, 2026.

To satisfy tax withholding obligations from these vestings, 26,292 shares of common stock were automatically sold in a mandated “sell to cover” transaction at a weighted average price of $13.8022 per share, within a range of $13.34 to $14.085. After these transactions, she directly held 298,386 shares of common stock and 187,500 RSUs.

Insider Trade Summary

Exercise and sale activity reported; no spread calculated

Exercise and Sale 6 txns

Insider Gessert Erica

Role Chief Financial Officer

Sold 26,292 shs ($363K)

Approx. gross sale proceeds $363K

Approx. exercise cost $0.00

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Units	37,500	$0.00	$0.00
Grant/Award	Restricted Stock Units	136,388	$0.00	$0.00
Exercise	Common Stock	37,500	$0.00	$0.00
Sale	Common Stock	26,292	$13.8022	$363K
Exercise	Performance Stock Units	40,477	$0.00	$0.00
Exercise	Common Stock	40,477	$0.00	$0.00

Holdings After Transaction: Performance Stock Units — 0 contracts (Direct); Restricted Stock Units — 323,888 contracts (Direct); Common Stock — 298,386 shares (Direct)

Footnotes (6)

1. F1. Each restricted stock unit ("RSU") or performance stock unit ("PSU") represents a contingent right to receive one share of the Issuer's common stock.
2. F2. 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 or PSUs 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. F3. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $13.34 to $14.085 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. F4. Represents earned PSUs that vested based on the achievement of performance criteria for a performance period that ended on December 31, 2025, as certified by the compensation committee of the board of directors of the Issuer on February 17, 2026. The earned PSUs vested 100% upon certification.
5. F5. 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.
6. F6. The RSUs vest in equal quarterly installments over four years beginning on May 18, 2026, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

FAQ

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What insider transactions did Upwork (UPWK) CFO Erica Gessert report?

Erica Gessert reported vesting and conversion of RSUs and PSUs into common stock, a new grant of 136,388 RSUs, and an automatic sale of 26,292 shares to cover tax withholding obligations tied to these equity awards.

How many Upwork (UPWK) shares did the CFO sell, and at what price?

The CFO had 26,292 Upwork common shares sold in an automatic “sell to cover” transaction at a weighted average price of $13.8022 per share, with individual sale prices ranging from $13.34 to $14.085 during the reported trading session.

Why were Upwork (UPWK) shares sold by the CFO in this Form 4?

The reported sale was required to cover tax withholding on vested RSUs and PSUs. Upwork’s equity plans mandate a “sell to cover” approach, so this transaction did not represent a discretionary trade by Erica Gessert personally.

What new restricted stock units did the Upwork (UPWK) CFO receive?

Erica Gessert received a grant of 136,388 restricted stock units. These RSUs are scheduled to vest in equal quarterly installments over four years starting May 18, 2026, contingent on her continued employment with Upwork on each vesting date.

How many Upwork (UPWK) shares does the CFO hold after these transactions?

Following the reported transactions, Erica Gessert directly held 298,386 shares of Upwork common stock. She also held 187,500 restricted stock units, each representing a contingent right to receive one additional share of Upwork common stock in the future.

How were Upwork (UPWK) performance stock units treated in this Form 4?

Earned performance stock units vested based on performance through December 31, 2025, as certified on February 17, 2026. Those PSUs converted into common stock immediately upon certification, and the related tax obligations were satisfied through the mandated sell-to-cover share sale.

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Form 4 Insider Transactions: What Each Field Means →

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Accepted by SEC EDGAR 02/19/2026 - 08:03 PM Learn about SEC filing dates

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

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

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)
02/17/2026

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	02/17/2026		M		40,477	A	(1)	287,178	D
Common Stock	02/18/2026		M		37,500	A	(1)	324,678	D
Common Stock	02/18/2026		S(2)		26,292	D	$13.8022(3)	298,386	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
Performance Stock Units	(1)	02/17/2026		M			40,477	(4)	(4)	Common Stock	40,477	$0.00	0.00	D
Restricted Stock Units	(1)	02/18/2026		M			37,500	(5)	(5)	Common Stock	37,500	$0.00	187,500	D
Restricted Stock Units	(1)	02/18/2026		A		136,388		(6)	(6)	Common Stock	136,388	$0.00	136,388	D

Explanation of Responses:

1. Each restricted stock unit ("RSU") or performance stock unit ("PSU") 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 or PSUs 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 $13.34 to $14.085 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. Represents earned PSUs that vested based on the achievement of performance criteria for a performance period that ended on December 31, 2025, as certified by the compensation committee of the board of directors of the Issuer on February 17, 2026. The earned PSUs vested 100% upon certification.

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.

6. The RSUs vest in equal quarterly installments over four years beginning on May 18, 2026, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Remarks:

	/s/ Jacob McQuown, Attorney-in-Fact	02/19/2026
	** 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).
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