Upwork CFO sells 22,844 shares in tax sale
Upwork, Inc. (UPWK) reported that Chief Financial Officer Erica Gessert settled vested equity awards and a related tax sale.
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Form Type
4
Rhea-AI Filing Summary
Upwork, Inc. (UPWK) reported that Chief Financial Officer Erica Gessert settled vested equity awards and a related tax sale. On August 18, 2026, RSUs covering 37,500 and 8,524 shares of common stock converted into an equal number of shares. On the same date, 22,844 shares were sold at a $8.4257 weighted average price, in a mandated “sell to cover” transaction to satisfy tax withholding obligations, rather than a discretionary trade. The underlying RSU grants vest over multi-year quarterly schedules, conditioned on continued employment.
Insider Trade Summary
Exercise and sale activity reported; no spread calculated
Exercise and Sale
5 txns
Insider
Gessert Erica
Role
Chief Financial Officer
Sold
22,844 shs ($192K)
Approx. gross sale proceeds
$192K
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Restricted Stock Units F1, F4 | 37,500 | $0.00 | $0.00 |
| Exercise | Restricted Stock Units F1, F5 | 8,524 | $0.00 | $0.00 |
| Exercise | Common Stock F1 | 37,500 | -- | -- |
| Exercise | Common Stock F1 | 8,524 | -- | -- |
| Sale | Common Stock F2, F3 | 22,844 | $8.4257 | $192K |
Holdings After Transaction:
Restricted Stock Units — 231,840 contracts (Direct);
Common Stock — 364,789 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 $8.37 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 25% on May 18, 2024 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.
- F5. 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: 22,844 shares
Weighted average sale price: $8.4257 per share
RSUs converted (grant 1): 37,500 RSUs
+5 more
8 metrics
Shares sold
22,844 shares
Common stock sale on August 18, 2026 to cover tax withholding
Weighted average sale price
$8.4257 per share
Sale of 22,844 shares on August 18, 2026; trades ranged from $8.37 to $8.45
RSUs converted (grant 1)
37,500 RSUs
RSUs converting into common stock on August 18, 2026
RSUs converted (grant 2)
8,524 RSUs
Additional RSUs converting into common stock on August 18, 2026
Total RSUs converted
46,024 RSUs
Sum of 37,500 and 8,524 RSUs converted to shares on August 18, 2026
Initial vesting tranche
25%
First vesting on May 18, 2024 for one RSU grant
Ongoing vesting fraction
1/16 of total shares
Quarterly vesting after initial 25% tranche, subject to continued employment
Second grant vesting period
Four years, quarterly
Equal quarterly installments beginning May 18, 2026, subject to continued employment
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"
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"
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"
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.
contingent right financial
"represents a contingent right to receive one share of the Issuer's"
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What insider transactions did UPWK CFO Erica Gessert report on August 18, 2026?
Erica Gessert reported RSU conversions into 37,500 and 8,524 shares of Upwork common stock, and a same-day sale of 22,844 shares at a $8.4257 weighted average price to cover tax withholding obligations from the RSU vesting.
How many Upwork (UPWK) RSUs vested or converted for the CFO on August 18, 2026?
Two RSU blocks converted on August 18, 2026: one covering 37,500 shares and another covering 8,524 shares of Upwork common stock, for a total of 46,024 shares delivered upon vesting.
What are the vesting schedules of the UPWK RSUs reported by the CFO?
One RSU grant vests 25% on May 18, 2024, then 1/16 of the total quarterly thereafter, subject to continued employment. A second grant vests in equal quarterly installments over four years beginning May 18, 2026, also conditioned on continued employment.
AI-generated analysis. How Rhea-AI works. Not financial advice.
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