Waystar CEO exercises options and executes 10b5-1 sale of 46,667 shares
Rhea-AI Filing Summary
Waystar Holding Corp. director and Chief Executive Officer Matthew J. Hawkins exercised vested stock options and sold the same shares under a pre-established Rule 10b5-1 trading plan adopted November 22, 2024. On 08/12/2025 he exercised options at an exercise price of $4.14 to acquire 46,667 shares and sold 46,667 shares in multiple transactions at a weighted average price of $34.6622 (range $34.44–$34.89 as disclosed).
Following these transactions the reporting person directly beneficially owned 764,131 shares. The filing also shows direct beneficial ownership of 1,289,745 stock options and indirect option holdings of 343,135 and 250,000 via grantor retained annuity trusts. The transactions are reported as occurring automatically pursuant to the 10b5-1 plan and the options involved were noted as vested.
Positive
- Transactions executed under a pre-established Rule 10b5-1 plan, adopted November 22, 2024, indicating pre-planned trading activity.
- Options were reported as vested, allowing lawful exercise and immediate disposition as disclosed.
Negative
- Director/CEO sold 46,667 shares, which reduced his direct beneficial ownership from 810,798 to 764,131 shares as shown on the form.
- Insider sale is material to insider liquidity (exercise at $4.14 and sale at weighted average $34.6622), which may be interpreted by some investors as cashing gains.
Insights
TL;DR: CEO exercised vested options at $4.14 and sold 46,667 shares at a weighted average of $34.6622 under a 10b5-1 plan.
The activity is a routine insider option exercise followed by an immediate planned sale, consistent with a Rule 10b5-1 program adopted on November 22, 2024. The exercise price of $4.14 versus the weighted average sale price of $34.6622 shows a large per-share gain on the exercised options; the filing reports the exact sale price range. This disclosure is procedural and provides transparency about timing and pricing of the transactions.
Impact assessment: Neutral for immediate valuation; informational for share-count and insider liquidity analysis.
TL;DR: Transactions were executed under a pre-established, documented 10b5-1 plan and options stated as vested; reporting is compliant and transparent.
The filer discloses that the sales were made pursuant to an affirmative defense plan, and the form specifies that the options were vested. The filing also itemizes direct and indirect beneficial option holdings, including amounts held in grantor retained annuity trusts. From a governance perspective, use of a documented plan reduces questions about opportunistic timing, and clear reporting of holdings and transaction prices supports regulatory compliance and market transparency.
Impact assessment: Not materially impactful to corporate governance beyond routine insider liquidity disclosure.
Insider Trade Summary
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Stock Options (right to buy) | 46,667 | $0.00 | -- |
| Exercise | Common Stock | 46,667 | $4.14 | $193K |
| Sale | Common Stock | 46,667 | $34.6622 | $1.62M |
| holding | Stock Options (right to buy) | -- | -- | -- |
| holding | Stock Options (right to buy) | -- | -- | -- |
Footnotes (1)
- These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on November 22, 2024 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 $34.44 to $34.89, 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.
