Waystar CEO Matthew Hawkins Exercises Options, Sells Shares

What Happened

• Matthew J. Hawkins, CEO of Waystar Holding Corp. (WAY), exercised vested stock options and immediately sold the resulting shares. On Aug 11 and Aug 13, 2026 he exercised a total of 82,500 options (22,462 on 8/11; 60,038 on 8/13) at $4.14 per share (total exercise cost $341,550) and sold the 82,500 shares in open‑market transactions for aggregate proceeds of $2,064,030. The filings show the sales were executed at weighted average prices of $25.04 (8/11) and $25.01 (8/13). Net proceeds before taxes/fees were roughly $1.72M.

Key Details

• Transaction dates: exercised & sold 2026-08-11 (22,462 shares) and 2026-08-13 (60,038 shares).
• Exercise price: $4.14 per share (total cost $341,550).
• Sale proceeds: $562,354 (8/11) and $1,501,676 (8/13); total ~$2,064,030.
• Total shares involved: 82,500.
• Shares owned after transaction: not specified in the provided filing excerpt.
• Notable footnotes:
  • F2: Transactions were automatic under a 10b5‑1 trading plan adopted Mar 13, 2026.
  • F5: The options exercised were vested.
  • F3/F4: Reported sale prices are weighted averages; individual trades ranged $25.00–$25.08 and $25.00–$25.05 respectively.
  • Some derivative lines report $0.00 price — these reflect internal accounting entries tied to the option exercises.
• Filing: Form 4 filed 2026-08-13 reporting transactions on 8/11 and 8/13; appears timely (Form 4 is typically due within two business days).

Context

• This was an exercise-and-sell (cashless-style) transaction: Hawkins exercised vested options and immediately sold the shares, which is common for executives to cover exercise costs and taxes. Because the trades were executed pursuant to a pre-arranged 10b5‑1 plan, they were automatic and not necessarily a fresh signal of sentiment.
• For retail investors, purchases by insiders can be more informative about conviction; routine option exercises followed by sales are often compensation/liquidity events rather than directional bets.