Waystar CEO Matthew Hawkins sells $2.14m in company stock

Matthew J. Hawkins, Chief Executive Officer and a Director of Waystar Holding Corp. (NASDAQ:WAY), sold 82,500 shares of the company’s common stock on September 2, 2026, for a total value of $2,142,582. The shares were sold at a weighted average price of $25.9707, with individual transactions ranging from $25.51 to $26.51 per share. This sale was conducted automatically pursuant to a pre-arranged trading plan adopted by Mr. Hawkins on March 13, 2026. The sale comes as the stock trades near $25.83, down 21% year-to-date, though InvestingPro analysis suggests the company remains undervalued at current levels.

On the same day, Mr. Hawkins acquired 82,500 shares of Waystar common stock by exercising stock options at a price of $4.14 per share, totaling $341,550. These options were vested at the time of exercise and are set to expire on November 1, 2027. This acquisition was also part of the same pre-arranged trading plan.

Additionally, on September 1, 2026, Mr. Hawkins disposed of 30,287 shares of Waystar common stock. These shares, valued at $779,284 at a price of $25.73 per share, were withheld to cover tax obligations associated with the vesting of restricted stock units (RSUs). The vesting schedule for these RSUs had been modified, with 25% vesting on September 1, 2026, and subsequent 25% vestings on the second, third, and fourth anniversaries of the vesting commencement date.

Following these transactions, Mr. Hawkins directly holds 1,804,794 shares of Waystar common stock, which includes unvested RSUs. He also directly holds 1,510,098 stock options and indirectly holds additional stock options through grantor retained annuity trusts. Analysts maintain an optimistic outlook on the $4.93 billion company, with seven analysts recently revising earnings upwards. For deeper insights, Waystar is covered in InvestingPro’s comprehensive Pro Research Report, available for over 1,400 US equities.

In other recent news, Waystar Holding reported strong second-quarter 2026 results, with revenue increasing by 18% to $320 million compared to the previous year. The company’s adjusted EBITDA rose by 21.5% to $137 million, indicating robust demand for its healthcare payment software. Following these results, Waystar raised its full-year revenue and adjusted EBITDA outlook, marking its ninth consecutive quarter of exceeding analyst consensus on revenue and EBITDA. Analysts have taken note of these developments, with BMO Capital and Mizuho both reiterating an Outperform rating for Waystar, setting price targets at $30.00 and $42.00, respectively. Meanwhile, Truist Securities adjusted its price target to $33 from $38 while maintaining a Buy rating, reflecting a revised financial model after the company’s latest earnings. KeyBanc also maintained an Overweight rating with a $30.00 price target, acknowledging the solid performance despite a dip in stock trading. These ratings and projections highlight Waystar’s ongoing growth potential and strategic positioning in the market.