Upwork (UPWK) CEO's 73K share sale splits tax and plan
Rhea-AI Filing Summary
UPWORK, INC (UPWK) reported insider transactions by President & CEO Hayden Brown on August 18, 2026. Brown had 46,822 Restricted Stock Units (RSUs) convert into an equal number of common shares, then sold a total of 73,241 shares of common stock. Of these, 23,241 shares were sold to cover tax-withholding obligations mandated by Upwork’s equity plans, while 50,000 shares were sold pursuant to a pre-arranged Rule 10b5-1 plan. The RSUs involved vest in scheduled quarterly installments over four years, contingent on continued employment.
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Insights
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Insider Trade Summary 10b5-1
Exercise and sale activity reported; no spread calculated
Exercise and Sale
8 txns
Insider
Brown Hayden
Role
President & CEO
Sold
73,241 shs ($617K)
Approx. gross sale proceeds
$617K
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Restricted Stock Units F1, F6 | 14,850 | $0.00 | $0.00 |
| Exercise | Restricted Stock Units F1, F7 | 18,333 | $0.00 | $0.00 |
| Exercise | Restricted Stock Units F1, F8 | 13,639 | $0.00 | $0.00 |
| Exercise | Common Stock F1 | 14,850 | -- | -- |
| Exercise | Common Stock F1 | 18,333 | -- | -- |
| Exercise | Common Stock F1 | 13,639 | -- | -- |
| Sale | Common Stock F2, F3 | 23,241 | $8.4257 | $196K |
| Sale | Common Stock F4, F5 | 50,000 | $8.4271 | $421K |
Holdings After Transaction:
Restricted Stock Units — 257,311 shares (Direct);
Common Stock — 771,076 shares (Direct)
Footnotes (8)
- 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 $8.37 to $8.45 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. This transaction was effected pursuant to a Rule 10b5-1 plan adopted by the Reporting Person on November 19, 2025.
- F5. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $8.245 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.
- F6. 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.
- F7. 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.
- F8. The RSUs vest in equal quarterly installments over four years beginning on May 18, 2026, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
Key Figures
Shares sold for tax withholding: 23,241 shares
Shares sold under Rule 10b5-1 plan: 50,000 shares
Total shares sold: 73,241 shares
+5 more
8 metrics
Shares sold for tax withholding
23,241 shares
Common stock sold August 18, 2026 to cover tax withholding obligations
Shares sold under Rule 10b5-1 plan
50,000 shares
Common stock sold August 18, 2026 pursuant to a Rule 10b5-1 plan
Total shares sold
73,241 shares
Aggregate common stock sales reported for August 18, 2026
Weighted average price (23,241-share sale)
$8.4257 per share
Multiple trades in the range $8.37–$8.45 per share
Weighted average price (50,000-share sale)
$8.4271 per share
Multiple trades in the range $8.245–$8.52 per share
RSU conversions
46,822 shares
RSUs converting into an equal number of UPWK common shares on August 18, 2026
Initial cliff vesting percentage
25%
One RSU grant vests 25% on February 18, 2024
Quarterly vesting rate
6.25%
Same RSU grant vests 6.25% of total shares each quarterly anniversary thereafter
Key Terms
Restricted Stock Units, sell to cover, Rule 10b5-1 plan, weighted average price
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
"require the satisfaction of 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.
Rule 10b5-1 plan regulatory
"This transaction was effected pursuant to a Rule 10b5-1 plan adopted"
A Rule 10b5-1 plan is a prearranged, written schedule that lets corporate insiders buy or sell company stock at set times or amounts, even if they later learn material nonpublic information. Think of it like setting an automatic thermostat for trades: it creates a clear record that trades were planned in advance, reducing the risk of insider-trading accusations and helping investors trust that insider transactions are routine rather than based on secret information.
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.
FAQ
What insider transactions did UPWK CEO Hayden Brown report on August 18, 2026?
Hayden Brown reported RSU conversions into 46,822 shares of Upwork common stock and sales totaling 73,241 shares on August 18, 2026. Some shares were sold to cover tax withholding, and others were sold under a Rule 10b5-1 trading plan.
How do Hayden Brown’s RSUs in UPWK vest according to this filing?
One RSU grant vests 25% on February 18, 2024, then 6.25% quarterly thereafter. Another vests in equal quarterly installments over four years beginning May 18, 2023, and a third vests in equal quarterly installments over four years beginning May 18, 2026, all subject to continued employment.
What does each RSU represent in Hayden Brown’s UPWK Form 4?
Each Restricted Stock Unit (RSU) represents a contingent right to receive one share of UPWORK, INC common stock. As RSUs vest, they convert into common shares, as reflected in the reported RSU conversions totaling 46,822 underlying shares.
AI-generated analysis. How Rhea-AI works. Not financial advice.
