Upwork CEO sells 23,893 shares in tax sale
Upwork’s CEO had RSUs vest and an automatic share sale to cover tax withholding obligations.
Rhea-AI Filing Summary
UPWORK, INC (UPWK) reported that President & CEO Hayden Brown had restricted stock units convert into 17,733 and 28,677 shares of common stock on September 18, 2026, as part of scheduled vesting. To cover tax withholding from these RSU vestings, 23,893 shares were automatically sold in a mandated “sell to cover” transaction at a weighted average price of $8.4509 per share, with no Rule 10b5-1 trading plan reported.
Positive
- None.
Negative
- None.
Insider Trade Summary
Exercise and sale activity reported; no spread calculated
Exercise and Sale
5 txns
Insider
Brown Hayden
Role
President & CEO
Sold
23,893 shs ($202K)
Approx. gross sale proceeds
$202K
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Restricted Stock Units F1, F4 | 17,733 | $0.00 | $0.00 |
| Exercise | Restricted Stock Units F1, F5 | 28,677 | $0.00 | $0.00 |
| Exercise | Common Stock F1 | 17,733 | -- | -- |
| Exercise | Common Stock F1 | 28,677 | -- | -- |
| Sale | Common Stock F2, F3 | 23,893 | $8.4509 | $202K |
Holdings After Transaction:
Restricted Stock Units — 393,175 contracts (Direct);
Common Stock — 793,593 shares (Direct)
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 $8.315 to $8.52 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.
- 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.
Key Figures
RSUs converted (grant 1): 17,733 units
RSUs converted (grant 2): 28,677 units
Shares sold to cover taxes: 23,893 shares
+5 more
8 metrics
RSUs converted (grant 1)
17,733 units
RSUs converting into common stock on September 18, 2026
RSUs converted (grant 2)
28,677 units
Additional RSUs converting into common stock on September 18, 2026
Shares sold to cover taxes
23,893 shares
Automatic “sell to cover” transaction on September 18, 2026
Weighted average sale price
$8.4509 per share
Sale of 23,893 shares to cover tax withholding
Sale price range
$8.315–$8.52 per share
Price range for multiple sale transactions included in the weighted average
Vesting period (2024 grant)
4 years
RSUs vest quarterly beginning June 18, 2024, subject to continued employment
Vesting period (2025 grant)
4 years
RSUs vest quarterly beginning June 18, 2025, subject to continued employment
Total RSUs converted
46,410 units
Sum of RSUs converting into common stock in this filing
Key Terms
Restricted Stock Units, sell to cover, weighted average price, contingent right
4 terms
Restricted Stock Units financial
"Each restricted stock unit ("RSU") represents a contingent right to receive one share"
Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.
sell to cover financial
"tax withholding obligations to be funded by a "sell to cover" transaction"
Sell to cover is when a person who receives company stock through options or awards sells just enough shares immediately to pay required taxes, exercise costs, or fees, keeping the rest. Think of it like cashing part of a bonus to cover the tax bill so you can keep the remainder. For investors, it can create predictable small selling pressure and slightly change the number of shares actually held by insiders without increasing long‑term dilution.
weighted average price financial
"The reported price in Column 4 is a weighted average price."
Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.
contingent right financial
"represents a contingent right to receive one share of the Issuer's common stock."
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What insider transaction did UPWK’s CEO report on September 18, 2026?
Hayden Brown reported RSU conversions into 17,733 and 28,677 UPWK common shares, followed by an automatic sale of 23,893 shares to cover tax withholding obligations related to those RSU vestings.
Was the UPWK CEO’s September 18, 2026 sale a discretionary trade?
No. The 23,893-share sale was mandated as a “sell to cover” transaction under Upwork’s equity incentive plans to fund tax withholding obligations from RSU vesting, and does not represent a discretionary trade by the CEO.
Were Hayden Brown’s UPWK transactions under a Rule 10b5-1 plan?
No. The filing’s Rule 10b5-1 checkbox is not affirmed, and the footnotes do not state that the transactions were made pursuant to a Rule 10b5-1 trading plan.
What are the vesting schedules for the UPWK CEO’s RSUs mentioned here?
One RSU grant vests in equal quarterly installments over four years beginning on June 18, 2024, and another grant vests in equal quarterly installments over four years beginning on June 18, 2025, subject to continued employment.
How many RSUs converted into UPWK common stock in this Form 4?
A total of 46,410 restricted stock units (17,733 plus 28,677) each converted into one share of UPWK common stock in connection with scheduled vesting on September 18, 2026.
AI-generated analysis. How Rhea-AI works. Not financial advice.
