Waystar CEO Matthew Hawkins sells $2.16m in shares

Waystar Holding Corp. CEO Matthew Hawkins divested approximately $2.16 million worth of shares on October 6, 2026. The sale comprised 82,500 shares of common stock, acquired via stock options exercised at $4.14 per share. The sale occurred in multiple transactions, with prices ranging from $25.98 to $26.60. The current trading price of the stock stands at $26.68, indicating a 7.5% gain over the past week.

Prior to selling, Hawkins had vested 82,500 shares, increasing his direct ownership to 1,804,794 shares, which also includes unvested restricted stock units. Waystar Holding Corp., valued at $5.12 billion, is considered undervalued by InvestingPro, trading at an attractive PEG ratio of 0.83. Hawkins also holds derivative holdings, including 1,427,598 directly owned stock options with an exercise price of $4.14 and indirect beneficial ownership through two grantor retained annuity trusts.

Recent reports suggest Waystar Holding is exploring strategic options, potentially returning to private ownership, following its initial public offering nearly two years ago. Morgan Stanley and Citi have maintained positive ratings on the stock, while other analysts have set higher price targets. The company's strategic position in AI monetization and reaffirmed long-term growth targets have garnered significant attention from investors and analysts.