Upwork COO sells 45,732 shares in tax sale
Upwork’s GM & COO had RSUs vest into shares, with part of the stock sold automatically to cover taxes under a mandated sell-to-cover arrangement.
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Form Type
4
Rhea-AI Filing Summary
UPWORK, INC (UPWK) reported that GM & Chief Operating Officer Anthony Ray Kappus had restricted stock units vest and convert into common stock on September 18, 2026. 114,860 RSUs converted into the same number of common shares, and a portion of those shares was sold to cover tax withholding obligations under the company’s mandated “sell to cover” policy, rather than as a discretionary trade. After this vesting event, Kappus held 344,582 RSUs directly.
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
45,732 shs ($386K)
Approx. gross sale proceeds
$386K
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Restricted Stock Units F1, F4 | 114,860 | $0.00 | $0.00 |
| Exercise | Common Stock F1 | 114,860 | -- | -- |
| Sale | Common Stock F2, F3 | 45,732 | $8.4508 | $386K |
Holdings After Transaction:
Restricted Stock Units — 344,582 contracts (Direct);
Common Stock — 76,342 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 $8.315 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 25% on September 18, 2026, and then 1/16th of the total number of shares on each quarterly anniversary thereafter, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
Key Figures
RSUs converted: 114,860 units
Common shares acquired: 114,860 shares
Shares sold: 45,732 shares
+3 more
6 metrics
RSUs converted
114,860 units
Restricted stock units vesting and converting into common stock on September 18, 2026
Common shares acquired
114,860 shares
Shares received upon RSU conversion on September 18, 2026
Shares sold
45,732 shares
Automatic sale to cover tax withholding obligations on September 18, 2026
Weighted average sale price
$8.4508 per share
Shares sold in multiple transactions between $8.315 and $8.52 per share
Remaining RSUs held
344,582 units
RSUs directly held by Anthony Ray Kappus after the reported vesting event
RSU vesting schedule
25% on September 18, 2026, then 1/16 quarterly
Vesting continues quarterly, subject to continued employment on each vesting date
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
"funded by a "sell to cover" transaction and does not represent a discretionary trade"
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 equity activity did UPWK’s GM & COO report on September 18, 2026?
UPWK’s GM & COO, Anthony Ray Kappus, reported the vesting and conversion of 114,860 RSUs into common stock, followed by an automatic sale of a portion of those shares to satisfy tax withholding obligations through a mandated “sell to cover” transaction.
How many UPWK restricted stock units vested and converted for Anthony Ray Kappus?
On September 18, 2026, 114,860 restricted stock units vested for Anthony Ray Kappus, each RSU representing a contingent right to receive one share of Upwork common stock, resulting in the acquisition of 114,860 common shares upon conversion.
How many UPWK RSUs does Anthony Ray Kappus hold after this transaction?
Following the September 18, 2026 vesting and conversion, Anthony Ray Kappus directly held 344,582 restricted stock units in UPWK, which continue to vest over time subject to his continued employment with the company.
Were the UPWK insider transactions by Anthony Ray Kappus under a Rule 10b5-1 plan?
No. The filing indicates no Rule 10b5-1 trading plan for these transactions. However, the sale of shares was still non-discretionary, as it was required by Upwork’s election to satisfy tax withholding obligations through a mandated “sell to cover” transaction.
AI-generated analysis. How Rhea-AI works. Not financial advice.
