Matthew J. Hawkins, Chief Executive Officer and Director of Waystar Holding Corp. (NASDAQ:WAY), filed a Form 4 on September 3, 2026, disclosing a series of transactions in common stock and stock options dated September 1 and September 2, 2026.

Key Highlights

  • Tax withholding: 30,287 shares of common stock were withheld on September 1, 2026, at $25.73 per share to cover taxes upon RSU vesting.
  • Option exercise: 82,500 stock options were exercised on September 2, 2026, at an exercise price of $4.14 per share (transaction code M).
  • Shares sold: 82,500 shares of common stock were sold on September 2, 2026, at a weighted average price of $25.9707, in a range from $25.51 to $26.51, pursuant to a Rule 10b5-1 plan adopted March 13, 2026.
  • Remaining ownership: Following all reported transactions, Hawkins directly beneficially owned 1,804,794 shares, including unvested RSUs.
  • Vesting schedule modification: The Talent and Compensation Committee modified the original vesting schedule for an RSU grant dated April 1, 2025; the modified schedule provides for 25% vesting on September 1, 2026, and 25% on each of the three subsequent anniversaries of the Vesting Commencement Date.
  • Remaining options: Hawkins held 1,510,098 directly owned stock options with an exercise price of $4.14 and an expiration date of November 1, 2027, following the reported exercise.

Waystar CEO Hawkins Discloses RSU Vest, Option Exercise, and 10b5-1 Sale

According to the filing, on September 1, 2026, Hawkins had 30,287 shares withheld at $25.73 per share to satisfy tax obligations arising from the vesting of restricted stock units originally granted on April 1, 2025. The filing states that the number of shares withheld was determined based on the actual sale price of shares sold in a "sell-to-cover" transaction. The RSU grant's vesting schedule was modified by the Talent and Compensation Committee from the original terms, which called for 40% vesting on the third anniversary and 60% on the fourth anniversary of the Vesting Commencement Date, to a revised schedule providing for 25% vesting on September 1, 2026, and 25% on each of the second, third, and fourth anniversaries of the Vesting Commencement Date.

On September 2, 2026, the filing discloses that Hawkins exercised 82,500 fully vested stock options at an exercise price of $4.14 per share (transaction code M), then sold those same 82,500 shares at a weighted average price of $25.9707, with individual sale prices ranging from $25.51 to $26.51 per share. The filing notes these transactions occurred automatically under a Rule 10b5-1(c) plan adopted by Hawkins on March 13, 2026. The filing further states that Hawkins undertakes to provide full information on the number of shares sold at each separate price upon request.

In addition to directly held options totaling 1,510,098 shares following the exercise, the filing discloses indirect holdings of 66,374 options held by a 2024 grantor retained annuity trust and 46,208 options held by a 2025 grantor retained annuity trust, both with an exercise price of $4.14 and an expiration date of November 1, 2027. The filing notes that changes in the form of beneficial ownership between direct and trust holdings reflect annuity payments exempt under Rule 16a-13, without a change in pecuniary interest.

What Was Disclosed

Hawkins's Form 4 reported RSU tax-withholding, an option exercise, and a 10b5-1 plan sale on September 1 and 2, 2026, along with a committee-modified RSU vesting schedule, leaving him with 1,804,794 directly beneficially owned shares including unvested RSUs.