Waystar CEO Matthew Hawkins sells $2.16m in shares

Matthew J. Hawkins, Chief Executive Officer and a Director at Waystar Holding Corp. (NASDAQ:WAY), sold shares totaling approximately $2.16 million on October 6, 2026. The sale involved 82,500 shares of common stock at a weighted average price of $26.2287 per share. The shares were sold in multiple transactions with prices ranging from $25.98 to $26.60. The stock currently trades at $26.68, reflecting a strong 7.5% gain over the past week.

Prior to the sale, Mr. Hawkins acquired 82,500 shares through the exercise of stock options at a price of $4.14 per share, totaling $341,550. These options were vested at the time of exercise. Both transactions were executed automatically under a Rule 10b5-1 trading plan, which Mr. Hawkins adopted on March 13, 2026.

Following these transactions, Mr. Hawkins directly holds 1,804,794 shares of Waystar common stock. This figure includes unvested restricted stock units. The company, valued at $5.12 billion, appears undervalued according to InvestingPro analysis and trades at an attractive PEG ratio of 0.83. For deeper insights, investors can access a comprehensive Pro Research Report on WAY, one of 1,400+ US equities covered on the platform.

His derivative holdings include 1,427,598 directly owned stock options with an exercise price of $4.14. Additionally, Mr. Hawkins holds indirect beneficial ownership of stock options through two grantor retained annuity trusts: 66,374 options via a 2024 trust and 46,208 options via a 2025 trust, both with an exercise price of $4.14.

In other recent news, Waystar Holding is reportedly exploring strategic options, including a potential sale that could return the company to private ownership. This development comes nearly two years after its initial public offering. Morgan Stanley has reiterated an Equalweight rating with a $28.00 price target, while Citi has maintained a Buy rating with the same price target, noting the exploration is unsurprising given recent mergers and acquisitions activity in the sector. BMO Capital and Mizuho have also reiterated their ratings, with BMO setting a price target of $30.00 and Mizuho a higher target of $42.00. BMO cited Waystar’s competitive advantages in AI monetization, while Mizuho highlighted the company’s reaffirmed long-term growth target of over 10% revenue growth. EQT and CPPIB remain significant shareholders, holding approximately 13% and 10% of the company, respectively. Waystar has not commented on the reports of a potential sale. These recent developments have attracted significant attention from investors and analysts alike.