Form 4: Waystar CTO Reports Share Sales and Option Exercises

Waystar Holding Corp.'s Chief Technology Officer, Christopher L. Schremser, reported the sale of shares for tax obligations and a pre-planned exercise and sale of stock options.

Summary

• Christopher L. Schremser, Chief Technology Officer of Waystar Holding Corp., reported multiple transactions involving the company's common stock and stock options.
• On June 6, 2025, 15,673 shares of common stock were withheld at a price of $40.55 per share to cover tax liabilities upon the vesting of Non-Qualified Stock Options granted on June 6, 2024. This transaction was not timely filed.
• On September 10, 2025, 8,623 stock options with an exercise price of $4.14 were exercised.
• Immediately following the option exercise on September 10, 2025, 8,623 shares of common stock were sold at a weighted average price of $40.4914, with individual sales ranging from $40.10 to $40.87.
• All transactions on September 10, 2025, were executed automatically pursuant to a Rule 10b5-1(c) plan adopted by Mr. Schremser on December 6, 2024.
• Following these reported transactions, Mr. Schremser beneficially owns 422,371 shares of common stock (which includes unvested RSUs) and 94,863 stock options.

Sentiment

Score: 5

Explanation: Neutral. The filing reports routine insider transactions (tax withholding, option exercise, and sell-to-cover) largely under a pre-planned 10b5-1 arrangement. The late filing of one transaction is a minor compliance issue but does not significantly alter the overall neutral sentiment regarding the company's prospects.

Positives

• The transactions on September 10, 2025, were executed under a pre-planned Rule 10b5-1(c) plan, indicating a structured approach to managing equity compensation rather than opportunistic trading.

Negatives

• One transaction, the withholding of shares for tax liabilities on June 6, 2025, was not timely filed, indicating a compliance lapse.

Industry Context

This filing reports routine insider transactions related to equity compensation and does not provide broader industry context or trends.

Stakeholder Impact

• Shareholders: Provides transparency regarding the equity holdings and transactions of a key executive. The pre-planned nature of the sales mitigates concerns about opportunistic insider selling.

Key Dates

Recommendation

The filing details routine insider transactions, including tax-related share withholding and a pre-planned exercise and sale of stock options. These actions are common for executives managing equity compensation and do not signal a change in the company's fundamental outlook or the executive's confidence. The minor compliance delay for one transaction is noted but does not warrant a change in investment thesis. Therefore, a 'hold' recommendation is appropriate as this filing provides no new material information to alter an existing investment decision.

Keywords

Waystar Holding Corp., WAY, Christopher L. Schremser, CTO, Form 4, Insider Trading, Stock Options, Share Sale, Rule 10b5-1, Tax Withholding, Equity Compensation