Waystar Insider Filing: 10b5‑1 Trades and Untimely Tax Withholding Disclosure
Rhea-AI Filing Summary
Christopher L. Schremser, Chief Technology Officer of Waystar Holding Corp. (WAY), reported multiple transactions. On 06/06/2025 he had 15,673 shares of Common Stock withheld to satisfy taxes on vested non‑qualified stock options at a closing price of $40.55, leaving him with 422,371 shares beneficially owned. Pursuant to a written plan intended to meet Rule 10b5‑1 affirmative defense conditions adopted 12/06/2024, on 09/10/2025 he was recorded as acquiring 8,623 stock options with a $4.14 strike and selling 8,623 shares in multiple transactions at weighted average prices in the $40.10–$40.87 range, returning beneficial ownership to 422,371 shares. The Form 4 notes the tax‑withholding transaction was not timely filed. The filing is signed by an attorney‑in‑fact, Gregory R. Packer, on 09/11/2025.
Positive
- Continued substantial ownership: Reporting person retains 422,371 shares after transactions
- Use of a documented 10b5‑1 plan: Transactions on 09/10/2025 occurred automatically under a plan adopted 12/06/2024
- Options acquired are vested: The filing states the reported options are currently vested
Negative
- Untimely disclosure: The Form 4 states the 06/06/2025 tax‑withholding transaction was not timely filed
- Sale of shares: 8,623 shares were sold on 09/10/2025 at prices ranging $40.10–$40.87, reducing liquid share count
- Tax withholding disposition: 15,673 shares were surrendered to cover taxes on vested options
Insights
TL;DR: Insider executed routine tax withholding and 10b5‑1 plan trades; holding remains sizable at 422,371 shares.
The reported transactions are largely administrative: tax withholding of 15,673 shares upon option vesting and automatic transactions under a 10b5‑1 plan that resulted in the sale of 8,623 shares and the acquisition of 8,623 stock options at a $4.14 strike. The filings confirm continued material ownership and that some equity is still subject to vesting. The late filing of the tax‑withholding disposition is a disclosure control lapse but does not, from this form alone, indicate other governance issues. Impact on investor value is likely minimal absent additional context.
TL;DR: Use of a documented 10b5‑1 plan is evident; late reporting of a withholding sale is noted.
The disclosure shows the reporting person adopted a written trading plan on 12/06/2024 and that certain transactions executed automatically under that plan on 09/10/2025. The form explicitly states the tax‑withholding transaction on 06/06/2025 was not timely filed, which is a procedural compliance issue requiring remediation. The signature by an attorney‑in‑fact is properly provided. Overall governance signals are mixed: documented trading plan is a compliance best practice, but the untimely Form 4 filing is a negative control point.
Insider Trade Summary
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Stock Options (right to buy) | 8,623 | $0.00 | -- |
| Exercise | Common Stock | 8,623 | $4.14 | $36K |
| Sale | Common Stock | 8,623 | $40.4914 | $349K |
| Tax Withholding | Common Stock | 15,673 | $40.55 | $636K |
Footnotes (1)
- 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. These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on December 6, 2024 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). Includes unvested RSUs. 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 $40.10 to $40.87, 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.
