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Waystar Holding Corp.·4

Jul 17, 5:21 PM ET

Hawkins Matthew J. 4

4 · Waystar Holding Corp. · Filed Jul 17, 2026

Research Summary

AI-generated summary of this filing

Updated

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

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.

Insider Transaction Report

Form 4
Period: 2026-07-15
Waystar Holding Corp.WAY
Hawkins Matthew J.
DirectorChief Executive Officer
Transactions
  • Exercise/Conversion

    Common Stock

    [F1][F2]
    2026-07-15$4.14/sh+33,099$137,030→ 959,915 total
  • Sale

    Common Stock

    [F3][F1][F2]
    2026-07-15$23.02/sh−33,099$762,032→ 926,816 total
  • Exercise/Conversion

    Common Stock

    [F1][F2]
    2026-07-16$4.14/sh+36,901$152,770→ 963,717 total
  • Sale

    Common Stock

    [F4][F1][F2]
    2026-07-16$23.09/sh−36,901$851,944→ 926,816 total
  • Exercise/Conversion

    Stock Options (right to buy)

    [F5]
    2026-07-15−33,099→ 1,435,238 total
    Exercise: $4.14Exp: 2027-11-01→ Common Stock (33,099 underlying)
  • Exercise/Conversion

    Stock Options (right to buy)

    [F5]
    2026-07-16−36,901→ 1,398,337 total
    Exercise: $4.14Exp: 2027-11-01→ Common Stock (36,901 underlying)
Holdings

  • Stock Options (right to buy)

    [F5][F6]
    Exercise: $4.14Exp: 2027-11-01→ Common Stock (1,468,337 underlying)
    1,398,337

  • Stock Options (right to buy)

    [F5]
    (indirect: By Trust)
    Exercise: $4.14Exp: 2027-11-01→ Common Stock (343,135 underlying)
    343,135

  • Stock Options (right to buy)

    [F5][F6]
    (indirect: By Trust)
    Exercise: $4.14Exp: 2027-11-01→ Common Stock (46,208 underlying)
    46,208
Footnotes (6)
  • [F1]Includes unvested RSUs.
  • [F2]These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on March 13, 2026 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).
  • [F3]The price reported in Column 4 is a weighted average price. These shares of common stock, par value $0.01 per share ("Common Stock") of Waystar Holding Corp. (the "Issuer") were sold in multiple transactions ranging from $23.00 to $23.08, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares of Common Stock sold at each separate price in the range set forth in this footnote.
  • [F4]The price reported in Column 4 is a weighted average price. These shares of common stock, par value $0.01 per share ("Common Stock") of Waystar Holding Corp. (the "Issuer") were sold in multiple transactions ranging from $23.00 to $23.27, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares of Common Stock sold at each separate price in the range set forth in this footnote.
  • [F5]These options are currently vested.
  • [F6]Reflects annuity payments resulting in a change in the form of beneficial ownership (direct and trust holdings) without a change in pecuniary interest, exempt under Rule 16a-13.
Signature
/s/ Gregory R. Packer, as Attorney-in-Fact|2026-07-17

Documents

1 file
  • 4
    wk-form4_1784323257.xmlPrimary

    FORM 4