Form 4: Waystar CEO Sells Shares After Option Exercise

Waystar Holding Corp. CEO Matthew J. Hawkins exercised stock options and immediately sold the acquired shares under a pre-arranged trading plan.

Summary

• Matthew J. Hawkins, Chief Executive Officer and Director of Waystar Holding Corp. (WAY), reported transactions on August 12, 2025.
• Hawkins exercised 46,667 stock options at an exercise price of $4.14 per share.
• Concurrently, he sold 46,667 shares of common stock at a weighted average price of $34.6622 per share.
• The sales occurred in a price range from $34.44 to $34.89 per share.
• These transactions were executed automatically under a Rule 10b5-1(c) trading plan adopted on November 22, 2024.
• Following these transactions, Hawkins directly beneficially owns 764,131 shares of common stock.
• He also holds 1,289,745 direct stock options and 593,135 indirect stock options (343,135 via a 2024 grantor retained annuity trust and 250,000 via a 2025 grantor retained annuity trust), all with an exercise price of $4.14 and an expiration date of November 1, 2027.

Sentiment

Score: 6

Explanation: The sentiment is neutral to slightly positive. While it's an insider sale, it was pre-planned under a 10b5-1 plan, indicating a scheduled event rather than a reaction to negative news. The significant profit realized from the option exercise is also a positive for the insider.

Positives

• The transactions were conducted under a pre-arranged Rule 10b5-1 trading plan, indicating a scheduled disposition rather than a reaction to new, negative information.
• The sale price of $34.6622 per share is significantly higher than the option exercise price of $4.14 per share, indicating a substantial profit for the insider on the exercised shares.

Negatives

• The disposition of shares by a key executive, even if pre-planned, can sometimes be perceived negatively by the market as it reduces the insider's direct equity stake.

Future Outlook

No forward-looking statements or guidance are provided in this insider transaction report.

Industry Context

This filing is an insider transaction report and does not provide information related to broader industry trends or competitors.

Related Party Transactions

• Indirect beneficial ownership of stock options is held through a 2024 grantor retained annuity trust (343,135 options) and a 2025 grantor retained annuity trust (250,000 options).

Stakeholder Impact

• Shareholders: The sale by a key executive, even if pre-planned, could lead to minor concerns about insider sentiment, though the Rule 10b5-1 plan mitigates this.
• Employees, Customers, Suppliers, Creditors: No direct impact on these stakeholders is indicated by this insider transaction report.

Key Dates

Recommendation

The filing details a pre-planned insider sale by the CEO, which is a routine event under a Rule 10b5-1 plan. While it represents a disposition of shares, the transaction was executed at a significant profit from the option exercise price, and the sale was scheduled in advance, mitigating concerns about immediate negative sentiment. This single transaction does not provide sufficient new information to alter a fundamental investment thesis, thus a 'hold' recommendation is appropriate.

Keywords

Waystar, WAY, insider trading, stock options, CEO, Form 4, Rule 10b5-1