Waystar Form 4: Hawkins Executes Options, Automatic 10b5-1 Sales
Rhea-AI Filing Summary
Matthew J. Hawkins, Chief Executive Officer and Director of Waystar Holding Corp. (WAY), reported multiple insider transactions. On 06/06/2025 he had 46,657 shares disposed at an average price of $40.55, resulting in reported beneficial ownership of 717,474 shares (which includes unvested RSUs). Subsequent automatic transactions under a plan intended to satisfy Rule 10b5-1 conditions show acquisitions of 12,200 and 12,800 shares on 09/22/2025 and 09/23/2025 at a $4.14 option price (with related sales at weighted average prices of about $38.08). The filing discloses holdings of exercisable stock options with a $4.14 exercise price and additional equity held indirectly through two grantor retained annuity trusts totaling 593,135 options reported indirectly.
Positive
- Substantial insider ownership retained: Reporting person continues to hold 717,474 shares directly, indicating alignment with shareholders.
- Use of 10b5-1 plan: Subsequent sales and acquisitions on 09/22/2025 and 09/23/2025 were executed under a pre-established plan, reducing risk of opportunistic trading.
- Options largely vested: Options reported as currently vested and exercisable, showing realized commitment through option exercise activity.
Negative
- Late reporting: The filing discloses the 06/06/2025 tax-withholding transaction was "not timely filed," which is a disclosure control lapse.
- Material disposals occurred: Disposal of 46,657 shares on 06/06/2025 reduced direct holdings and may be viewed as significant insider sells (though due to tax withholding).
Insights
TL;DR: Routine insider option exercises and sales under a pre-established trading plan; current direct holding remains material.
The filing documents standard executive equity activity: tax-withholding share disposals tied to option vesting, exercises at a $4.14 strike, and contemporaneous market sales executed under an affirmative 10b5-1 plan on 09/22/2025 and 09/23/2025. The reporting person still holds 717,474 shares directly, plus significant option positions and indirect trust holdings, which maintain substantial insider ownership alignment with shareholders. The late filing note for the June 6, 2025 withholding is disclosed but the explanatory footnote clarifies the reason.
TL;DR: Transactions appear governed by pre-set plans and include standard tax-withholding mechanics; timely disclosure issues were noted.
The report shows use of a 10b5-1 trading plan to effect share sales and option exercises, which is common for executives to manage legal risk. However, the form discloses one transaction was "not timely filed," specifying shares withheld for taxes on vested options. Although the filing provides explanatory detail and current balances, the late reporting item is a governance point investors may review in the companys disclosure controls context.
Insider Trade Summary
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Stock Options (right to buy) | 12,800 | $0.00 | -- |
| Exercise | Common Stock | 12,800 | $4.14 | $53K |
| Sale | Common Stock | 12,800 | $38.0789 | $487K |
| Exercise | Stock Options (right to buy) | 12,200 | $0.00 | -- |
| Exercise | Common Stock | 12,200 | $4.14 | $51K |
| Sale | Common Stock | 12,200 | $38.0792 | $465K |
| Tax Withholding | Common Stock | 46,657 | $40.55 | $1.89M |
| holding | Stock Options (right to buy) | -- | -- | -- |
| holding | Stock Options (right to buy) | -- | -- | -- |
Footnotes (1)
- Includes unvested RSUs. This transaction was not timely filed. The transaction represents shares of common stock withheld to pay taxes upon vesting of Non-Qualified Stock Options granted to the Reporting Person on June 6, 2024. The number of shares withheld was determined on June 6, 2025, based on the closing price of WAY common stock on that date. The ending balance reported herein is accurate and reflects the Reporting Person's current holdings. These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on June 6, 2025 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). 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 $38.00 to $38.20, 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. 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 $38.00 to $38.16, 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. These options are currently vested.
