Erica Gessert - 18 Jun 2026 Form 4 Insider Report for UPWORK, INC (UPWK)

Reporting relationship: Chief Financial Officer
Issuer ticker: UPWK
Reported as of: 18 Jun 2026
Net transaction value: -$74,734
SEC form: 4
Accepted by SEC: 23 Jun 2026, 17:18:34 UTC
Prior SEC filing: 20 May 2026
Source filing: View source filing
Reporting owner signature: /s/ Jacob McQuown, Attorney-in-Fact

Key filing fact

Erica Gessert filed Form 4 for UPWORK, INC (UPWK) on 23 Jun 2026.

Key facts

This page summarizes Erica Gessert's Form 4 filing for UPWORK, INC (UPWK).
5 reported transactions and 2 derivative rows are listed below.
Accepted by SEC: 23 Jun 2026, 17:18.

Change

Previous filing in this sequence was filed on 20 May 2026.
Current net transaction value: -$74,734.

Research use

This tells you what this filing adds before you inspect full transaction and derivative tables.
You can trace every row back to the original SEC filing document.

Evidence

Filed on Form 4

Ownership activity is grounded in SEC Form 4 disclosures.

View source filing

Reporting Owners (1)

CIK 0001975669 Primary reporting owner

Gessert Erica

Relationship: Chief Financial Officer
Address: C/O UPWORK INC., 530 LYTTON AVENUE, SUITE 301, PALO ALTO
Signature: /s/ Jacob McQuown, Attorney-in-Fact
Signature date: 23 Jun 2026

Reported non-derivative transactions

Shares, units, or other non-derivative securities reported in this filing.

UPWK transaction

Common Stock

Options Exercise

Transaction value
Shares: +8,432
Change %: +2.5%
Price
Shares after: 341,078
Date: 18 Jun 2026
Ownership: Direct
Footnotes: F1

UPWK transaction

Common Stock

Options Exercise

Transaction value
Shares: +9,700
Change %: +2.8%
Price
Shares after: 350,778
Date: 18 Jun 2026
Ownership: Direct
Footnotes: F1

UPWK transaction

Common Stock

Sale

Transaction value: $74,734
Shares: -9,169
Change %: -2.6%
Price: $8.15
Shares after: 341,609
Date: 18 Jun 2026
Ownership: Direct
Footnotes: F2, F3

Reported derivative securities

Options, warrants, convertible securities, or similar derivative positions disclosed in the filing.

UPWK transaction Derivative

Restricted Stock Units

Options Exercise

Transaction value
Shares: -8,432
Change %: -12%
Price: $0.000000^*
Shares after: 59,031
Date: 18 Jun 2026
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 8,432
Exercise price
Footnotes: F1, F4

UPWK transaction Derivative

Restricted Stock Units

Options Exercise

Transaction value
Shares: -9,700
Change %: -8.3%
Price: $0.000000^*
Shares after: 106,697
Date: 18 Jun 2026
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 9,700
Exercise price
Footnotes: F1, F5

^* marks a reported price that did not pass the local price check.

Additional SEC filing notes

Filing notes and footnotes

Explanation of responses 5 footnotes

Footnote F1

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

Footnote 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 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.

Footnote F3

The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $8.02 to $8.25 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.

Footnote F4

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.

Footnote F5

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.