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  4. [Form 4] Upwork Inc. Insider Trading Activity

Upwork CFO's Stock Sale Tied to RSU Vesting, Not Strategic Exit

Filing Impact
(Moderate)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Upwork CFO Erica Gessert reported multiple transactions on June 18, 2025, involving restricted stock units (RSUs) and common stock:

  • Acquired 8,433 RSUs that vest quarterly over four years from June 18, 2024
  • Acquired 9,699 RSUs that vest quarterly over four years from June 18, 2025
  • Sold 9,267 shares at weighted average price of $13.51 per share in a mandatory "sell to cover" transaction to satisfy tax obligations

Following these transactions, Gessert directly owns 190,738 shares of common stock, plus 92,762 and 145,496 unvested RSUs from two separate grants. The share sale was not discretionary but rather mandated by Upwork's equity incentive plan to cover tax withholding requirements.

Positive

  • None.

Negative

  • None.
Insider Gessert Erica
Role Chief Financial Officer
Sold 9,267 shs ($125K)
Type Security Shares Price Value
Exercise Restricted Stock Units 8,433 $0.00 --
Exercise Restricted Stock Units 9,699 $0.00 --
Exercise Common Stock 8,433 $0.00 --
Exercise Common Stock 9,699 $0.00 --
Sale Common Stock 9,267 $13.5054 $125K
Holdings After Transaction: Restricted Stock Units — 92,762 shares (Direct); Common Stock — 190,306 shares (Direct)
Footnotes (1)
  1. Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock. 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. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $13.24 to $13.73 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. 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. 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.
Form 4 Insider Transactions: What Each Field Means →
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)
06/18/2025
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 06/18/2025 M 8,433 A (1) 190,306 D
Common Stock 06/18/2025 M 9,699 A (1) 200,005 D
Common Stock 06/18/2025 S(2) 9,267 D $13.5054(3) 190,738 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) 06/18/2025 M 8,433 (4) (4) Common Stock 8,433 $0.00 92,762 D
Restricted Stock Units (1) 06/18/2025 M 9,699 (5) (5) Common Stock 9,699 $0.00 145,496 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 $13.24 to $13.73 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 06/23/2025
** 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.

Source: View Original Filing on SEC EDGAR

FAQ

What insider trading activity occurred at UPWK on June 18, 2025?

UPWK's Chief Financial Officer Erica Gessert exercised 18,132 Restricted Stock Units (8,433 + 9,699 RSUs) that converted to common stock, and subsequently sold 9,267 shares at an average price of $13.5054 per share to cover tax withholding obligations.

How many UPWK shares does CFO Erica Gessert own after the June 18, 2025 transactions?

Following the reported transactions, CFO Erica Gessert directly owns 190,738 shares of UPWK common stock. She also holds 92,762 unvested RSUs from one grant and 145,496 unvested RSUs from another grant.

What was the vesting schedule for UPWK CFO's Restricted Stock Units?

The RSUs vest in two separate schedules: one grant vests in equal quarterly installments over four years beginning June 18, 2024, and another grant vests in equal quarterly installments over four years beginning June 18, 2025. Both are subject to continued employment.

Was UPWK CFO Erica Gessert's stock sale discretionary?

No, the sale was not discretionary. The sale of 9,267 shares was mandated by Upwork's equity incentive plans to cover tax withholding obligations through a 'sell to cover' transaction following the RSU vesting.

What was the price range of UPWK shares sold by the CFO on June 18, 2025?

The shares were sold in multiple transactions at prices ranging from $13.24 to $13.73 per share, with a weighted average price of $13.5054 per share.