Waystar CEO exercises options and sells shares
Waystar Holding Corp. Chief Executive Officer Matthew J. Hawkins reported option exercises and related share sales.
Rhea-AI Filing Summary
Waystar Holding Corp. Chief Executive Officer Matthew J. Hawkins reported option exercises and related share sales. He exercised stock options for 82,500 shares of common stock at an exercise price of $4.14 per share and sold the same number of shares in open-market transactions at weighted average prices of $25.0358 and $25.0121 per share. These trades were executed pursuant to a Rule 10b5-1(c) trading plan adopted on March 13, 2026. Hawkins continues to hold vested options indirectly through 2024 and 2025 grantor retained annuity trusts covering 343,135 and 46,208 underlying shares, respectively.
Positive
- None.
Negative
- None.
Insider Trade Summary 10b5-1
Exercise and Sale: 82,500 shares ($1.72M approx. pre-tax spread)
Exercise and Sale
8 txns
Insider
Hawkins Matthew J.
Role
Chief Executive Officer
Sold
82,500 shs ($2.06M)
Approx. gross sale proceeds
$2.06M
Approx. exercise cost
$342K
Approx. pre-tax spread
$1.72M
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Stock Options (right to buy) F5 | 60,038 | $0.00 | $0.00 |
| Exercise | Common Stock F1, F2 | 60,038 | $4.14 | $249K |
| Sale | Common Stock F4, F1, F2 | 60,038 | $25.0121 | $1.50M |
| Exercise | Stock Options (right to buy) F5 | 22,462 | $0.00 | $0.00 |
| Exercise | Common Stock F1, F2 | 22,462 | $4.14 | $93K |
| Sale | Common Stock F3, F1, F2 | 22,462 | $25.0358 | $562K |
| holding | Stock Options (right to buy) F5 | -- | -- | -- |
| holding | Stock Options (right to buy) F5 | -- | -- | -- |
Holdings After Transaction:
Stock Options (right to buy) — 1,315,837 contracts (Direct);
Common Stock — 1,835,081 shares (Direct);
Stock Options (right to buy) — 343,135 contracts (Indirect, By 2024 grantor retained annuity trust);
Stock Options (right to buy) — 46,208 contracts (Indirect, By 2025 grantor retained annuity trust)
Footnotes (5)
- 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 $25.00 to $25.08, 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 $25.00 to $25.05, 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.
Key Figures
Options exercised: 82,500 shares
Exercise price: $4.14 per share
Shares sold: 82,500 shares
+4 more
7 metrics
Options exercised
82,500 shares
Total common shares acquired via option exercises on August 11 and 13, 2026 at $4.14
Exercise price
$4.14 per share
Exercise or conversion price of stock options exercised into Waystar common stock
Shares sold
82,500 shares
Common shares sold in open-market or private transactions on August 11 and 13, 2026
Weighted average sale price (Aug 11)
$25.0358 per share
Weighted average sale price for 22,462 shares sold in multiple trades ranging $25.00–$25.08
Weighted average sale price (Aug 13)
$25.0121 per share
Weighted average sale price for 60,038 shares sold in multiple trades ranging $25.00–$25.05
Remaining options via 2024 GRAT
343,135 underlying shares
Indirect stock options held by 2024 grantor retained annuity trust at $4.14, expiring Nov. 1, 2027
Remaining options via 2025 GRAT
46,208 underlying shares
Indirect stock options held by 2025 grantor retained annuity trust at $4.14, expiring Nov. 1, 2027
Key Terms
Rule 10b5-1(c), weighted average price, grantor retained annuity trust, Stock Options (right to buy)
4 terms
Rule 10b5-1(c) regulatory
"plan adopted by the Reporting Person on March 13, 2026 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c)"
Rule 10b5-1(c) is an SEC guideline that lets company insiders set up a written, pre-planned schedule to buy or sell their company stock when they are not in possession of material, nonpublic information. For investors, it matters because such plans can reduce the appearance of insider trading by separating decisions from inside knowledge—like putting your trades on autopilot—while also requiring scrutiny since pre-planned trades can still affect market confidence and share value.
weighted average price financial
"The price reported in Column 4 is a weighted average price. These shares of common stock"
Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.
grantor retained annuity trust financial
"By 2024 grantor retained annuity trust"
A grantor retained annuity trust (GRAT) is an estate-planning tool where the person who creates the trust transfers assets into it but receives fixed cash payments (an annuity) from the trust for a set number of years; whatever remains after that term passes to designated beneficiaries. It matters to investors because it can shift future appreciation of assets out of the creator’s taxable estate—like putting an asset into a timed vending machine that pays you fixed amounts while any extra value that grows inside the machine goes to heirs with reduced gift or estate tax consequences.
Stock Options (right to buy) financial
"Stock Options (right to buy)"
FAQ
What did Waystar (WAY) CEO Matthew J. Hawkins report in this Form 4?
Hawkins reported exercising options for 82,500 shares of Waystar common stock at $4.14 per share and selling the same number of shares in open-market transactions at weighted average prices above $25 per share.
Were the Waystar (WAY) CEO’s transactions made under a Rule 10b5-1 plan?
Yes. The filing states the transactions occurred automatically under a Rule 10b5-1(c) trading plan adopted by Matthew J. Hawkins on March 13, 2026, indicating they were pre-arranged rather than discretionary trades.
What stock options did the Waystar (WAY) CEO exercise in this filing?
Hawkins exercised vested stock options to acquire 82,500 shares of Waystar common stock at an exercise price of $4.14 per share. The options are described as currently vested and carry an expiration date of November 1, 2027.
What derivative holdings does the Waystar (WAY) CEO still have after these transactions?
He continues to hold vested stock options indirectly through grantor retained annuity trusts covering 343,135 and 46,208 underlying Waystar common shares, each with an exercise price of $4.14 and expiring on November 1, 2027.
AI-generated analysis. How Rhea-AI works. Not financial advice.
