Form 4: Waystar CEO Exercises Stock Options and Sells Shares Under Pre-Arranged 10b5-1 Plan

Waystar Holding Corp.'s CEO, Matthew J. Hawkins, executed a pre-planned transaction on June 10, 2025, involving the exercise of stock options and the subsequent sale of a portion of common stock.

Summary

• Matthew J. Hawkins, the Chief Executive Officer and a Director of Waystar Holding Corp. (WAY), reported transactions involving the company's common stock on June 10, 2025.
• Mr. Hawkins acquired 46,667 shares of common stock by exercising vested stock options at a price of $4.14 per share.
• Following the option exercise, he disposed of (sold) 2,704 shares of common stock at a weighted average price of $40.5733 per share, with individual sales ranging from $40.13 to $41.07.
• Both the acquisition and disposition were conducted automatically pursuant to a Rule 10b5-1(c) trading plan, which was adopted by Mr. Hawkins on November 22, 2024.
• After these reported transactions, Mr. Hawkins directly beneficially owns 764,131 shares of Waystar Holding Corp. common stock.
• He also directly beneficially owns 1,226,214 stock options (right to buy) with an exercise price of $4.14 and an expiration date of November 1, 2027.
• Additionally, Mr. Hawkins indirectly beneficially owns 750,000 stock options through grantor retained annuity trusts (500,000 via a 2024 trust and 250,000 via a 2025 trust), also 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 there is insider selling, it is a relatively small amount compared to total holdings, executed under a pre-planned Rule 10b5-1 plan, and follows a profitable option exercise. This suggests routine equity management and diversification rather than a negative signal about the company's future prospects.

Positives

• The CEO exercised options at a significantly lower price ($4.14) compared to the market price at which shares were sold (weighted average $40.5733), indicating a profitable transaction for the insider.
• The transactions were executed under a Rule 10b5-1 plan, which signifies pre-planned, non-discretionary trades, often viewed as less concerning than opportunistic insider selling.

Negatives

• The CEO sold shares, which, regardless of being pre-planned, can sometimes be perceived negatively by some investors as it reduces direct insider ownership.

Risks

• This Form 4 filing primarily reports insider transactions and does not contain information regarding operational, financial, or strategic risks of Waystar Holding Corp.

Future Outlook

This Form 4 filing is solely for reporting insider transactions and does not contain any forward-looking statements or guidance regarding Waystar Holding Corp.'s future financial performance, strategic plans, or operational outlook.

Management Comments

• "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 $40.13 to $41.07, 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."

Industry Context

This filing is a routine disclosure of insider equity transactions and does not provide insights into broader industry trends, competitive dynamics, or Waystar's market position within the healthcare technology or revenue cycle management sector. It reflects an individual executive's personal financial planning rather than a company-wide strategic development.

Comparison to Industry Standards

• This document reports on insider trading activity, which is a standard regulatory disclosure for publicly traded companies across all industries.
• It does not contain financial or operational metrics that can be directly compared to industry benchmarks or the performance of competitors such as R1 RCM, Change Healthcare, or Optum, as its focus is on individual equity transactions rather than company-level results.

Stakeholder Impact

• Shareholders: Provides transparency regarding the equity holdings and transactions of a key executive. The pre-planned nature and relatively small size of the sale may mitigate concerns about insider selling.
• Employees, Customers, Suppliers, Creditors: No direct impact on these stakeholders is indicated by this routine insider transaction report.

Next Steps

• The Reporting Person has undertaken to provide full information regarding the number of shares of Common Stock sold at each separate price within the reported range upon request from the Issuer, any security holder, or the SEC staff.

Key Dates

Recommendation

Keywords

Waystar Holding Corp., WAY, SEC Form 4, Insider Trading, Stock Options, Rule 10b5-1 Plan, Matthew J. Hawkins, CEO, Director, Equity Sales, Beneficial Ownership