Upwork (UPWK) CEO Hayden Brown sells shares, converts 46,822 RSUs
Filing Impact
Filing Sentiment
Form Type
4
Rhea-AI Filing Summary
Upwork, Inc.’s President & CEO Hayden Brown reported both stock sales and equity vesting activity. On May 18, 2026, she sold a total of 72,546 shares of common stock in open‑market transactions, including 50,000 shares at a weighted average price of $8.5695 per share and 22,546 shares at $8.6634 per share. Footnotes state that part of these sales were required "sell to cover" transactions to fund tax withholding on vesting restricted stock units, and that one sale was executed under a pre‑arranged Rule 10b5‑1 plan adopted on November 19, 2025, indicating the timing was not fully discretionary.
On the same date, Brown exercised or converted 46,822 restricted stock units into common stock at a conversion price of $0.00, in three tranches of 13,638, 18,334 and 14,850 RSUs, following quarterly vesting schedules tied to continued employment. A footnote also notes 1,544 shares acquired through the company’s employee stock purchase plan on May 14, 2026. The share balances reported after these transactions show that she continues to hold a substantial direct equity position in Upwork.
Positive
- None.
Negative
- None.
Insider Trade Summary 10b5-1
Net Seller: 72,546 shares ($623,800)
Net Sell
8 txns
Insider
Brown Hayden
Role
President & CEO
Sold
72,546 shs ($624K)
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Restricted Stock Units | 14,850 | $0.00 | -- |
| Exercise | Restricted Stock Units | 18,334 | $0.00 | -- |
| Exercise | Restricted Stock Units | 13,638 | $0.00 | -- |
| Exercise | Common Stock | 14,850 | $0.00 | -- |
| Exercise | Common Stock | 18,334 | $0.00 | -- |
| Exercise | Common Stock | 13,638 | $0.00 | -- |
| Sale | Common Stock | 22,546 | $8.6634 | $195K |
| Sale | Common Stock | 50,000 | $8.5695 | $428K |
Holdings After Transaction:
Restricted Stock Units — 44,550 shares (Direct, null);
Common Stock — 815,126 shares (Direct, null)
Footnotes (1)
- Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock. Reflects 1,544 shares acquired under the Issuer's employee stock purchase plan on May 14, 2026. 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 $8.57 to $8.73 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 November 19, 2025. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $8.10 to $8.79 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, 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. 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: 72,546 shares
First sale block price: $8.5695 per share
Second sale block price: $8.6634 per share
+3 more
6 metrics
Shares sold
72,546 shares
Total common stock sold on May 18, 2026
First sale block price
$8.5695 per share
Weighted average price for 50,000 shares sold
Second sale block price
$8.6634 per share
Weighted average price for 22,546 shares sold
RSUs converted
46,822 units
Restricted stock units converted to common stock on May 18, 2026
ESPP acquisition
1,544 shares
Shares acquired under employee stock purchase plan on May 14, 2026
Rule 10b5-1 plan date
November 19, 2025
Adoption date of trading plan covering one sale
Key Terms
Restricted Stock Units, Rule 10b5-1 plan, sell to cover, employee stock purchase plan, +1 more
5 terms
Restricted Stock Units financial
"The RSUs vest 25% on February 18, 2024, and then 6.25%..."
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.
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.
sell to cover financial
"required to be sold ... 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.
employee stock purchase plan financial
"Reflects 1,544 shares acquired under the Issuer's employee stock purchase plan..."
An employee stock purchase plan is a company program that lets workers buy shares through small payroll deductions, often at a discount to the market price and after a set offering period. Think of it like a workplace savings plan that turns into ownership: it encourages employees to share in the company’s success and can create predictable buying or selling of stock that investors watch because it affects supply, demand and employee incentives.
tax withholding obligations financial
"to cover tax withholding obligations in connection with the vesting of the RSUs..."
FAQ
What did Upwork (UPWK) CEO Hayden Brown report in this Form 4?
Hayden Brown reported a mix of stock sales and equity vesting activity. She sold 72,546 Upwork common shares and converted 46,822 restricted stock units into shares, while also reflecting shares acquired through the employee stock purchase plan in mid-May 2026.
Were Hayden Brown’s Upwork (UPWK) stock sales discretionary or pre-planned?
The filing indicates the sales were partly non‑discretionary. Some shares were sold to cover tax withholding obligations on RSU vesting, and another sale was executed under a Rule 10b5‑1 trading plan adopted on November 19, 2025, making the timing pre‑scheduled.
What restricted stock unit (RSU) activity did the Upwork (UPWK) CEO report?
Brown reported exercises or conversions of 46,822 RSUs into common stock on May 18, 2026, in tranches of 13,638, 18,334, and 14,850 units. These RSUs vest in quarterly installments over four years, conditioned on her continued employment with Upwork.
What do the vesting schedules look like for the CEO’s Upwork (UPWK) RSUs?
The RSUs vest over four years in quarterly installments. One award vests 25% on February 18, 2024, then 6.25% quarterly, while others vest in equal quarterly installments starting May 18, 2023 and May 18, 2026, contingent on continued employment.