Upwork CFO sells 9,336 shares for taxes
Upwork’s CFO had 18,133 RSUs vest and converted, selling 9,336 shares solely to cover tax withholding obligations at a weighted average price of about $8.45.
Rhea-AI Filing Summary
UPWORK, INC (UPWK) Chief Financial Officer Erica Gessert reported routine equity compensation activity on September 18, 2026. Two tranches of restricted stock units totaling 18,133 RSUs vested and were converted into an equal number of common shares. Of these, 9,336 shares of common stock were sold at a weighted average price of $8.4508 per share to cover tax withholding obligations under the company’s equity incentive plans, as a mandatory “sell to cover” transaction rather than a discretionary trade. The RSUs vest in equal quarterly installments over four years beginning June 18, 2024 and June 18, 2025, subject to continued employment, and no Rule 10b5-1 trading plan is reported.
Positive
- None.
Negative
- None.
Insider Trade Summary
Exercise and sale activity reported; no spread calculated
Exercise and Sale
5 txns
Insider
Gessert Erica
Role
Chief Financial Officer
Sold
9,336 shs ($79K)
Approx. gross sale proceeds
$79K
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Restricted Stock Units F1, F4 | 8,433 | $0.00 | $0.00 |
| Exercise | Restricted Stock Units F1, F5 | 9,700 | $0.00 | $0.00 |
| Exercise | Common Stock F1 | 8,433 | -- | -- |
| Exercise | Common Stock F1 | 9,700 | -- | -- |
| Sale | Common Stock F2, F3 | 9,336 | $8.4508 | $79K |
Holdings After Transaction:
Restricted Stock Units — 147,595 contracts (Direct);
Common Stock — 373,586 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: 18,133 units
First RSU tranche: 8,433 units
Second RSU tranche: 9,700 units
+4 more
7 metrics
RSUs converted
18,133 units
Total restricted stock units vesting and converting into common stock on September 18, 2026
First RSU tranche
8,433 units
RSUs vesting and converting into common stock from the grant beginning June 18, 2024
Second RSU tranche
9,700 units
RSUs vesting and converting into common stock from the grant beginning June 18, 2025
Shares sold for taxes
9,336 shares
Common shares sold in a mandated “sell to cover” transaction on September 18, 2026
Weighted average sale price
$8.4508 per share
Average price for 9,336 shares sold to cover tax withholding obligations
Sale price range
$8.315–$8.52 per share
Range of prices for multiple transactions included in the weighted average sale
RSU vesting term (each grant)
4 years, quarterly
RSUs vest in equal quarterly installments over four years starting June 18, 2024 and June 18, 2025
Key Terms
Restricted Stock Units, sell to cover, weighted average price, equity incentive plans, +1 more
5 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.
equity incentive plans financial
"mandated by the Issuer's election under its equity incentive plans to require"
Equity incentive plans are company programs that pay employees, executives, or directors with company stock, stock options, or share units instead of or in addition to cash, aiming to align their interests with shareholders—like giving team members a stake in the house they help build. For investors this matters because such plans can motivate better company performance but also dilute existing ownership and increase reported compensation costs, so they affect future earnings, voting power, and share value.
tax withholding obligations financial
"shares required to be sold by the Reporting Person to cover tax withholding obligations"
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What did UPWK CFO Erica Gessert report in this Form 4 transaction?
Erica Gessert reported the vesting and conversion of 18,133 RSUs into common stock on September 18, 2026, and the sale of 9,336 shares at a weighted average price of $8.4508 per share to cover tax withholding obligations.
How many UPWK RSUs vested for the CFO on September 18, 2026?
Two RSU tranches vested for a total of 18,133 restricted stock units, consisting of 8,433 RSUs from one grant and 9,700 RSUs from another, each converting into the same number of shares of Upwork common stock.
What are the vesting schedules for the CFO’s UPWK RSUs mentioned here?
One RSU grant vests in equal quarterly installments over four years beginning on June 18, 2024, and another vests in equal quarterly installments over four years beginning on June 18, 2025, each subject to the CFO’s continuing employment with Upwork.
Was a Rule 10b5-1 trading plan used for this UPWK Form 4 activity?
No. The filing indicates that no Rule 10b5-1 trading plan is reported. The sale described was instead mandated by the company’s equity incentive plan as a tax “sell to cover” transaction.
AI-generated analysis. How Rhea-AI works. Not financial advice.
