Kappus Anthony Ray 4

What Happened
Anthony Kappus, Chief Operating Officer of Upwork (UPWK), had 5,114 restricted stock units (RSUs) convert into common shares on May 18, 2026. To satisfy tax withholding on the vesting, 1,905 of those shares were sold in the open market at a weighted average price of $8.66 for total proceeds of $16,504. The filing also shows the derivative position for 5,114 RSUs was converted (reported as a $0 disposition of the derivative) and 5,114 shares were acquired — resulting in a net increase of approximately 3,209 shares retained by Kappus.

Key Details

• Transaction date: May 18, 2026; Form 4 filed May 20, 2026.
• Sale: 1,905 shares disposed at a weighted average price of $8.66 (range $8.57–$8.73) for $16,504 (footnote F3).
• Conversion/Exercise: 5,114 RSUs converted to 5,114 common shares (derivative disposition reported at $0) (codes M).
• Net retained from this vesting: 5,114 acquired − 1,905 sold = ~3,209 shares retained.
• Shares owned after transaction: not specified in the filing.
• Notable footnotes: F1 explains RSUs equal one share each on vesting; F2 confirms the 1,905-share sale was a mandatory "sell to cover" for taxes (not a discretionary sale); F4 notes these RSUs vest in equal quarterly installments over four years beginning May 18, 2026.
• Timeliness: Filed two days after the transaction date; no late-filing flag indicated.

Context
This was primarily a routine RSU vesting event, not an independent open-market purchase or a discretionary sale for investment reasons. The sale of 1,905 shares was a mandated sell-to-cover for tax withholding, which is common in equity compensation plans. The derivative code (M) indicates conversion/exercise of the RSU award into common shares.