Kappus Anthony Ray 4
4 · UPWORK, INC · Filed Jul 21, 2026
Research Summary
AI-generated summary of this filing
Upwork (UPWK) COO Anthony Kappus Sells 558 Shares
What Happened
Anthony Kappus, Chief Operating Officer of Upwork (UPWK), had RSUs vest on July 18, 2026 that converted into 1,412 shares. To satisfy tax withholding, 558 of those shares were sold in an open-market "sell-to-cover" transaction at a weighted average price of $9.06, generating $5,053. The RSU conversion/settlement is also reported as a derivative transaction (showing the conversion/disposition of the RSUs).
Key Details
- Transaction date: July 18, 2026 (reported on Form 4 filed July 21, 2026). The filing shows the trades occurred on 7/18 and the Form 4 was filed 3 days later.
- Sale: 558 shares disposed at a weighted average price of $9.06 per share (range $9.01–$9.12). Proceeds: $5,053. (Footnote F3 explains the weighted average and price range.)
- RSU conversion: 1,412 RSUs converted/settled into shares on 7/18 (reported as derivative transactions). One derivative entry shows acquisition/conversion; another shows the RSUs surrendered/settled. (Footnote F1 explains each RSU = 1 share.)
- Tax withholding: The 558-share sale was a mandatory "sell-to-cover" to satisfy tax-withholding obligations, not a discretionary sale by the insider (Footnote F2).
- Vesting schedule: These RSUs vest in equal quarterly installments over four years beginning July 18, 2026 (Footnote F4).
- Shares owned after the transaction: Not specified in the provided data.
Context
This was a routine RSU settlement with a sell-to-cover for taxes rather than an individual choosing to sell stock for investment reasons. For derivative/RSU transactions, it’s common to see a conversion of units to shares and an immediate partial sale to cover withholding. Such mandated sell-to-cover transactions generally should not be interpreted as a bearish signal by themselves.
Insider Transaction Report
- Exercise/Conversion
Common Stock
[F1]2026-07-18+1,412→ 4,621 total - Sale
Common Stock
[F2][F3]2026-07-18$9.06/sh−558$5,053→ 4,063 total - Exercise/Conversion
Restricted Stock Units
[F1][F4]2026-07-18−1,412→ 21,191 total→ Common Stock (1,412 underlying)
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 $9.01 to $9.12 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 July 18, 2026, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.