WAY insider: 16,666 options exercised at $4.14 and shares sold at ~$40.49
Rhea-AI Filing Summary
Waystar Holding Corp. insider transactions by CFO Steven M. Oreskovich. On 06/06/2025 14,038 shares were withheld to satisfy taxes upon vesting of non‑qualified stock options, reported at a price of $40.55, leaving 354,512 shares beneficially owned. On 09/10/2025 the reporting person acquired 16,666 shares by exercising options at a $4.14 exercise price under a plan intended to satisfy Rule 10b5‑1, and on the same date sold 16,666 shares in multiple transactions at a weighted average price of $40.4925, returning beneficial ownership to 354,512 shares. The reporting person holds 101,205 stock options following these events. The filing discloses that the June 6, 2025 tax‑withholding transaction was not timely filed.
Positive
- Exercise at low strike: 16,666 options exercised at a $4.14 strike price, enabling potential value realization.
- Use of 10b5‑1 plan: September transactions occurred under a plan adopted 09/06/2024, indicating preplanned trading to mitigate timing concerns.
- Substantial option holdings remain: Reporting person retains 101,205 stock options, showing continued alignment with equity incentives.
Negative
- Late filing: The June 6, 2025 tax‑withholding transaction "was not timely filed," indicating a disclosure compliance lapse.
- Significant sale activity: Sale of 16,666 shares on 09/10/2025 reduced freely held shares, which may be viewed negatively by some investors.
- Tax withholding reduced share count: 14,038 shares withheld for taxes decreased beneficial ownership on 06/06/2025.
Insights
TL;DR: Insider exercised low strike options and sold shares at a significantly higher market price; transactions appear routine but include a late filing.
The reporting shows exercise of 16,666 options at a $4.14 strike with concurrent sales at a weighted average of $40.4925, indicating material insider liquidity realization. The report also documents withholding of 14,038 shares for taxes upon option vesting. Holding of 101,205 options remains significant. These actions are commonly used by executives to diversify or cover tax obligations; the filing notes a not timely filing for the June withholding, which raises a disclosure compliance issue but not necessarily a company operational concern.
TL;DR: Transactions largely occurred pursuant to a 10b5‑1 plan, reducing insider timing risk, but a late report signals a compliance lapse.
The 09/10/2025 transactions are stated to have occurred automatically under a plan adopted 09/06/2024 intended to meet Rule 10b5‑1 affirmative defense conditions, which supports procedural compliance for scheduled trades. However, the disclosure that the 06/06/2025 tax‑withholding transaction "was not timely filed" is a clear procedural deficiency and could prompt follow‑up from compliance or regulators. No other regulatory or litigation items are disclosed in this Form 4.
Insider Trade Summary
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Stock Options (right to buy) | 16,666 | $0.00 | -- |
| Exercise | Common Stock | 16,666 | $4.14 | $69K |
| Sale | Common Stock | 16,666 | $40.4925 | $675K |
| Tax Withholding | Common Stock | 14,038 | $40.55 | $569K |
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. Includes unvested RSUs. These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on September 6, 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 $40.09 to $40.90, 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.
