Tax-driven share sale by Upwork (UPWK) CFO after RSU vesting
Filing Impact
Filing Sentiment
Form Type
4
Rhea-AI Filing Summary
Upwork CFO Erica Gessert reported routine equity transactions involving RSU vesting, tax withholding, and resulting share ownership. She sold 22,162 shares of common stock at a weighted average price of $8.6634 per share in an open-market transaction that, according to the disclosure, was required to cover tax withholding obligations from RSU vesting rather than a discretionary trade.
On the same date, she exercised restricted stock units that converted into a total of 46,024 shares of common stock (8,524 shares from one RSU grant and 37,500 shares from another). After these transactions, she held 346,284 shares of common stock directly, while continuing to hold RSU awards that vest over time under quarterly schedules described in the disclosure.
Positive
- None.
Negative
- None.
Insider Trade Summary
Net Seller: 22,162 shares ($191,998)
Net Sell
5 txns
Insider
Gessert Erica
Role
Chief Financial Officer
Sold
22,162 shs ($192K)
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Restricted Stock Units | 37,500 | $0.00 | -- |
| Exercise | Restricted Stock Units | 8,524 | $0.00 | -- |
| Exercise | Common Stock | 37,500 | $0.00 | -- |
| Exercise | Common Stock | 8,524 | $0.00 | -- |
| Sale | Common Stock | 22,162 | $8.6634 | $192K |
Holdings After Transaction:
Restricted Stock Units — 150,000 shares (Direct, null);
Common Stock — 346,284 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. 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. 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: 22,162 shares
Weighted average sale price: $8.6634 per share
RSUs exercised into common stock: 46,024 shares
+4 more
7 metrics
Shares sold
22,162 shares
Tax-related sale on 2026-05-18 to cover RSU withholding
Weighted average sale price
$8.6634 per share
Open-market sale on 2026-05-18
RSUs exercised into common stock
46,024 shares
8,524 + 37,500 underlying shares from RSU conversions
Common shares held after transactions
346,284 shares
Direct ownership following 2026-05-18 activity
RSUs remaining from one grant
127,864 RSUs
Post-transaction balance for one RSU award
RSUs remaining from another grant
150,000 RSUs
Post-transaction balance for second RSU award
ESPP shares acquired
1,544 shares
Employee stock purchase plan on 2026-05-14
Key Terms
restricted stock unit ("RSU"), employee stock purchase plan, sell to cover, weighted average price
4 terms
restricted stock unit ("RSU") financial
"Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock."
employee stock purchase plan financial
"Reflects 1,544 shares acquired under the Issuer's employee stock purchase plan on May 14, 2026."
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.
sell to cover financial
"required to be sold ... to be 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. These shares were sold in multiple transactions at prices ranging"
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.
FAQ
What did Upwork (UPWK) CFO Erica Gessert report in this Form 4?
Upwork CFO Erica Gessert reported RSU vesting, a tax-related share sale, and updated holdings. She sold 22,162 shares to cover tax withholding and exercised 46,024 RSUs into common stock, ending with 346,284 shares held directly plus additional unvested RSUs.
What RSU vesting schedules are disclosed for Upwork (UPWK) CFO Erica Gessert?
One RSU grant vests 25% on May 18, 2024, with the remainder vesting in sixteenth increments on each quarterly anniversary thereafter. Another grant vests in equal quarterly installments over four years beginning May 18, 2026, contingent on continued employment with Upwork.