UPWK Form 4: CEO Hayden Brown 10b5-1 Sale and RSU Vesting Change Ownership
Rhea-AI Filing Summary
Upwork Inc. director and President & CEO Hayden Brown reported multiple transactions in August 2025 that changed her beneficial ownership of Upwork (UPWK) common stock. On August 15, 2025 she sold 60,000 shares under a Rule 10b5-1 plan at a weighted-average price of $13.7575, leaving her with 1,093,485 shares. Between August 18, 2025 transfers and vesting converted RSUs into shares, adding a total of 50,383 shares, and a "sell to cover" sale of 25,577 shares occurred to satisfy tax withholding at a weighted-average price of $13.8352. After these events her reported beneficial ownership is 1,118,291 shares. Several RSU awards remain subject to future vesting schedules.
Positive
- Use of Rule 10b5-1 plan for the 60,000-share sale, indicating the transaction was pre-established and not opportunistic
- Continued substantial ownership: the reporting person still beneficially owns 1,118,291 shares after transactions
- RSU vesting disclosed with clear schedules, showing alignment with long-term compensation structures
Negative
- Insider sold 85,577 shares total (60,000 under 10b5-1 and 25,577 sell-to-cover), reducing reported holdings
- Weighted-average sale prices of $13.7575 and $13.8352 indicate dispositions near mid-$13 per share range
Insights
TL;DR: Insider sold shares under a pre-established 10b5-1 plan and sold shares to cover taxes after RSU vesting; overall holding remains over one million shares.
The transactions include a planned sale of 60,000 shares under a Rule 10b5-1 plan and a mandatory "sell to cover" of 25,577 shares tied to RSU vesting. The RSU vesting converted 50,383 units into common stock, increasing share count before withholding. The use of a 10b5-1 plan indicates the large sale was prearranged and not an ad hoc disposition. Net change reduces reported beneficial ownership from the pre-sale level but leaves the reporting person with a substantial stake of 1,118,291 shares.
TL;DR: Transactions appear procedural and governance-compliant: planned trading and mandatory tax-withholding sales after RSU vesting.
The filing documents compliance with Rule 10b5-1 and issuer-mandated "sell to cover" for tax withholding, which are standard mechanisms to manage insider liquidity and tax obligations. Multiple RSU schedules are disclosed with vesting timelines, showing continued alignment with long-term incentive structures. No indication of unusual or opportunistic trades beyond the pre-arranged plan and mandatory withholding.
Insider Trade Summary
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Restricted Stock Unit | 9,589 | $0.00 | -- |
| Exercise | Restricted Stock Unit | 7,610 | $0.00 | -- |
| Exercise | Restricted Stock Unit | 14,850 | $0.00 | -- |
| Exercise | Restricted Stock Unit | 18,334 | $0.00 | -- |
| Exercise | Common Stock | 9,589 | $0.00 | -- |
| Exercise | Common Stock | 7,610 | $0.00 | -- |
| Exercise | Common Stock | 14,850 | $0.00 | -- |
| Exercise | Common Stock | 18,334 | $0.00 | -- |
| Sale | Common Stock | 25,577 | $13.8352 | $354K |
| Sale | Common Stock | 60,000 | $13.7575 | $825K |
Footnotes (1)
- This transaction was effected pursuant to a Rule 10b5-1 plan adopted by the Reporting Person on December 6, 2024. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $13.64 to $14.01 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. 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 $13.74 to $13.987 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 25% on February 18, 2023, and then 6.25% of the total shares vest on each quarterly anniversary thereafter, subject to the Reporting Person's continued employment with the Issuer on each vesting date. The RSUs vest in equal quarterly installments over four years beginning on May 18, 2022, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date. The RSUs vest 25% on February 18, 2024, and then 6.25% of the total shares vest on each quarterly anniversary thereafter, subject to the Reporting Person's continued employment with the Issuer on each vesting date. The RSUs vest in equal quarterly installments over four years beginning on May 18, 2023, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
