Hawkins Matthew J. 4

What Happened

• Matthew J. Hawkins, CEO of Waystar Holding Corp., exercised options to acquire a total of 70,000 shares (33,099 on 2026-07-15 and 36,901 on 2026-07-16) at $4.14 per share (total exercise cost ≈ $289,800) and then sold those 70,000 shares in open-market transactions for aggregate proceeds of about $1,613,976 (sales on 7/15 and 7/16 at weighted average prices of $23.02 and $23.09).
• The exercises and immediate sales effectively converted option/derivative holdings into cash (a cashless-like outcome). The filing also shows derivative-disposal entries at $0.00 (classified as derivative transactions), which reflect settlement/conversion activity rather than market sales.

Key Details

• Transaction dates and prices:
  • 2026-07-15: Exercised 33,099 shares at $4.14 (acquired $137,030); sold 33,099 shares at weighted avg $23.02 (≈ $762,032).
  • 2026-07-16: Exercised 36,901 shares at $4.14 (acquired $152,770); sold 36,901 shares at weighted avg $23.09 (≈ $851,944).
• Total exercised: 70,000 shares; total proceeds from sales: ≈ $1.61M; total exercise cost: ≈ $290k.
• Shares owned after the transactions: not specified in the Form 4 filing.
• Notable footnotes:
  • F2: Transactions occurred automatically under a 10b5-1 trading plan adopted March 13, 2026.
  • F3/F4: Reported sale prices are weighted averages; actual sale prices ranged $23.00–$23.08 and $23.00–$23.27 across multiple trades; the filer can provide a per-price breakdown on request.
  • F1: Filing includes unvested RSUs in holdings; F5: options exercised were vested; F6: some entries reflect annuity/form changes exempt under Rule 16a-13.
• Filing date: Form 4 filed 2026-07-17 (transactions on 7/15–7/16), which appears timely.

Context

• This pattern — exercising vested options and promptly selling the resulting shares — is common among executives to realize gains or cover tax/option costs; the presence of a 10b5-1 plan indicates the sales were pre-planned and automatic, not ad hoc market-timing decisions.
• Derivative entries with $0.00 prices denote settlement/conversion of awards rather than open-market sales; they do not represent cash proceeds.