Gessert Erica 4

4 · UPWORK, INC · Filed Jun 23, 2026

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Updated Jun 23, 2026

UPWK CFO Erica Gessert Sells Shares After RSU Vesting

What Happened

Erica Gessert, Chief Financial Officer of Upwork, Inc. (UPWK), had restricted stock units (RSUs) convert to common stock on June 18, 2026 and a portion of the resulting shares were sold to satisfy tax withholding. The filing shows conversions of 8,432 and 9,700 RSUs and a weighted-average open-market sale of 9,169 shares at $8.15 for total proceeds of $74,734. Two additional disposition entries (8,432 and 9,700 shares) are reported at $0 and reflect shares withheld to cover tax obligations.

Key Details

Transaction date: 2026-06-18; Form 4 filed: 2026-06-23 (reporting the 6/18 transactions).
Open-market sale: 9,169 shares at a weighted average price of $8.15; proceeds $74,734. Reported sale prices ranged $8.02–$8.25 per share (footnote F3).
Conversions/dispositions: 8,432 and 9,700 RSUs converted to shares; those same amounts were shown as disposed at $0 to satisfy tax withholding (footnote F2).
Footnotes: F1 explains RSUs represent rights to one share each; F4/F5 describe quarterly vesting schedules for the two RSU grants; F2 indicates the sell-to-cover was mandated by the company’s plan.
Shares owned after the transactions are not specified in the provided excerpt.

Context

These entries reflect RSU vesting and routine sell-to-cover tax withholding rather than a discretionary stock sale. Derivative code "M" here indicates conversion/settlement of RSUs to common stock. Such sell-to-cover transactions are common when equity awards vest and do not necessarily signal insider sentiment about the company.

Form 4

Period: 2026-06-18

Chief Financial Officer

Transactions

Exercise/Conversion
Common Stock
[F1]
2026-06-18+8,432→ 341,078 total
Exercise/Conversion
Common Stock
[F1]
2026-06-18+9,700→ 350,778 total
Sale
Common Stock
[F2][F3]
2026-06-18$8.15/sh−9,169$74,734→ 341,609 total
Exercise/Conversion
Restricted Stock Units
[F1][F4]
2026-06-18−8,432→ 59,031 total
→ Common Stock (8,432 underlying)
Exercise/Conversion
Restricted Stock Units
[F1][F5]
2026-06-18−9,700→ 106,697 total
→ Common Stock (9,700 underlying)

Footnotes (5)

[F1]Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.
[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.
[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.
[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.
[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.

Signature

/s/ Jacob McQuown, Attorney-in-Fact|2026-06-23

1 file