Upwork (UPWK) GM Dave Bottoms sells 18,575 shares after RSU vesting
Rhea-AI Filing Summary
Upwork, Inc. GM, Marketplace Dave Bottoms reported a mix of RSU vesting and share sales. On March 18, 2026, he converted a total of 20,908 Restricted Stock Units into an equal number of common shares at a conversion price of $0.00 per share, reflecting routine equity compensation vesting.
On the same day, he sold 11,575 common shares at a weighted average price of $12.3118 per share, followed by an additional sale of 7,000 shares on March 19, 2026 at a weighted average price of $11.4926 per share. Footnotes state that part of the shares sold were required to cover tax withholding obligations through a “sell to cover” transaction under Upwork’s equity incentive plans, meaning those sales were not discretionary trades.
Another footnote explains that the transactions were effected pursuant to a Rule 10b5-1 trading plan adopted on May 30, 2025, indicating the sales were pre-planned. After these transactions, Bottoms directly holds 2,678 shares of Upwork common stock, alongside ongoing RSU awards that vest in equal quarterly installments over four-year periods beginning on December 18, 2022, June 18, 2024, and June 18, 2025, subject to continued employment.
Positive
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Negative
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Insights
Routine RSU vesting with pre-planned and tax-driven sales; limited signal.
Dave Bottoms, GM of Marketplace at Upwork, reported conversion of 20,908 RSUs into common shares and total open-market sale activity of 18,575 shares. The data and footnotes show a standard equity compensation cycle rather than an abrupt portfolio shift.
One block of shares was sold to satisfy tax withholding obligations via a mandated “sell to cover” mechanism under the company’s equity plans, which is mechanical and not a discretionary decision. A separate footnote states the transactions were executed under a Rule 10b5-1 trading plan adopted on May 30, 2025, suggesting the timing was pre-scheduled.
Following these transactions, Bottoms holds 2,678 shares directly, and the RSU tables indicate continued unvested awards with quarterly vesting over four-year terms starting on December 18, 2022, June 18, 2024, and June 18, 2025. Given the pre-planned and tax-driven nature of much of the activity, this filing appears routine and is unlikely to materially alter an informed view of Upwork’s equity story.
Insider Trade Summary 10b5-1
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Sale | Common Stock | 7,000 | $11.4926 | $80K |
| Exercise | Restricted Stock Units | 8,980 | $0.00 | -- |
| Exercise | Restricted Stock Units | 6,024 | $0.00 | -- |
| Exercise | Restricted Stock Units | 5,904 | $0.00 | -- |
| Exercise | Common Stock | 8,980 | $0.00 | -- |
| Exercise | Common Stock | 6,024 | $0.00 | -- |
| Exercise | Common Stock | 5,904 | $0.00 | -- |
| Sale | Common Stock | 11,575 | $12.3118 | $143K |
Footnotes (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 $12.13 to $12.52 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. This transaction was effected pursuant to a Rule 10b5-1 plan adopted by the Reporting Person on May 30, 2025. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $11.33 to $11.72 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 December 18, 2022, 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, 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.
