Waystar (WAY) CEO Matthew Hawkins Exercises Options, Sells Shares

What Happened

• Matthew J. Hawkins, Chief Executive Officer of Waystar Holding Corp. (WAY), exercised options and sold shares in early September 2026. On Sept. 2 he exercised/converted 82,500 shares (exercise price $4.14) and sold those 82,500 shares in the open market at a weighted average price of $25.97 for proceeds of approximately $2,142,583.
• On Sept. 1, 30,287 shares were withheld (sold-to-cover) to satisfy taxes on vesting RSUs at $25.73 per share, producing proceeds of about $779,285. The filing also reports a derivative conversion line at $0 tied to the exercise/conversion process.

Key Details

• Transaction dates and prices:
  • 2026-09-01: 30,287 shares withheld for taxes at $25.73 — $779,285 (reported as tax withholding, Code F).
  • 2026-09-02: Exercised/converted 82,500 shares at $4.14 (Acquired), sold 82,500 shares at weighted avg $25.97 — $2,142,583 (open market sale, Code S). Sale prices ranged $25.51–$26.51 per share (weighted average reported).
• Shares owned after transaction: Not disclosed in the provided filing.
• Notable footnotes:
  • F1: Tax-withholding (sell-to-cover) was for RSUs that vested; vesting schedule was modified (25% vested Sept 1, 2026, then 25% each year thereafter).
  • F2: Filing includes unvested RSUs.
  • F3: Some transactions were automatic under a 10b5-1 trading plan.
  • F4: Reported sale price is a weighted average across multiple trades ($25.51–$26.51).
  • F5: The options exercised were vested.
• Timeliness: Reported on 2026-09-03 for transactions on 2026-09-01 and 2026-09-02 — appears to be filed within the Form 4 two-business-day reporting window.

Context

• This was effectively a cashless exercise: vested/vestable options were exercised (paid at $4.14 per share) and most or all of the resulting shares were sold in the open market the same day. Tax-withholding via sell-to-cover on RSU vesting is routine and not necessarily an indicator of confidence change.
• The presence of a 10b5-1 plan note indicates some sales occurred under a pre-arranged trading plan, which is intended to insulate the insider from allegations of trading on non-public information.