Kappus Anthony Ray 4

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.