Upwork COO sells 1,964 shares in tax sale
UPWORK, INC (UPWK) reported that executive Anthony Ray Kappus, GM & Chief Operating Officer, had 5,115 Restricted Stock Units (RSUs) convert into an equal number of shares of common stock on August 18, 2026.
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Form Type
4
Rhea-AI Filing Summary
UPWORK, INC (UPWK) reported that executive Anthony Ray Kappus, GM & Chief Operating Officer, had 5,115 Restricted Stock Units (RSUs) convert into an equal number of shares of common stock on August 18, 2026. A portion of these shares, 1,964 shares, was sold at a weighted average price of $8.4257 per share to cover tax withholding obligations, as mandated by the company’s equity incentive plan "sell to cover" election and not as a discretionary trade. Following the RSU conversion, 71,604 RSUs remain subject to vesting in equal quarterly installments over four years beginning on May 18, 2026, contingent on Mr. Kappus’s continued employment.
Insider Trade Summary
Exercise and sale activity reported; no spread calculated
Exercise and Sale
3 txns
Insider
Kappus Anthony Ray
Role
GM & Chief Operating Officer
Sold
1,964 shs ($17K)
Approx. gross sale proceeds
$17K
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Restricted Stock Units F1, F4 | 5,115 | $0.00 | $0.00 |
| Exercise | Common Stock F1 | 5,115 | -- | -- |
| Sale | Common Stock F2, F3 | 1,964 | $8.4257 | $17K |
Holdings After Transaction:
Restricted Stock Units — 71,604 contracts (Direct);
Common Stock — 7,214 shares (Direct)
Footnotes (4)
- 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. 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
RSUs converted: 5,115 RSUs
Shares sold: 1,964 shares
Weighted average sale price: $8.4257 per share
+3 more
6 metrics
RSUs converted
5,115 RSUs
RSUs converted into an equal number of common shares on August 18, 2026
Shares sold
1,964 shares
Common stock sold to cover tax withholding obligations on August 18, 2026
Weighted average sale price
$8.4257 per share
Weighted average price for 1,964 shares sold in the range $8.37–$8.45
Remaining RSUs
71,604 RSUs
RSUs reported as held following the RSU conversion transaction
RSU vesting term
Four years
RSUs vest in equal quarterly installments over four years beginning May 18, 2026
Vesting start date
May 18, 2026
Start date for quarterly RSU vesting schedule, subject to continued employment
Key Terms
Restricted Stock Units, sell to cover, weighted average price, vesting
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""
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.
vesting financial
"in connection with the vesting of the RSUs listed in Table II."
Vesting is the process by which you earn full ownership of something, like company stock or a retirement benefit, over time. It’s like earning the right to keep a gift piece by piece the longer you stay with a company, making sure employees stay committed before they receive all the benefits.
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What insider transactions did UPWK executive Anthony Ray Kappus report on this Form 4?
Anthony Ray Kappus reported the conversion of 5,115 RSUs into common stock and the sale of 1,964 shares of UPWORK, INC common stock on August 18, 2026, primarily to satisfy tax withholding obligations under a mandated "sell to cover" arrangement.
How many Restricted Stock Units does Anthony Ray Kappus still hold at UPWK?
After the reported RSU conversion, Anthony Ray Kappus has 71,604 RSUs reported as remaining. According to the filing, these RSUs vest in equal quarterly installments over four years beginning on May 18, 2026, subject to continued employment.
What vesting schedule applies to Anthony Ray Kappus’s UPWK RSUs?
The filing states that the RSUs vest in equal quarterly installments over four years, beginning on May 18, 2026. Vesting is conditioned on Anthony Ray Kappus’s continuing employment with UPWORK, INC on each vesting date.
AI-generated analysis. How Rhea-AI works. Not financial advice.
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