Waystar CEO sells 82,500 shares after option exercise
Rhea-AI Filing Summary
Waystar Holding Corp. (WAY) reported that Chief Executive Officer and director Matthew J. Hawkins exercised stock options for 82,500 shares of common stock at an exercise price of $4.14 per share on September 2, 2026, then sold 82,500 shares at a weighted average price of $25.9707 per share. The exercise and sale were effected automatically under a trading plan adopted on March 13, 2026 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). On September 1, 2026, 30,287 shares were withheld at $25.73 per share to pay taxes upon vesting of restricted stock units, and the filing notes a modified RSU vesting schedule. Hawkins continues to hold vested stock options on common stock, including positions held directly and through 2024 and 2025 grantor retained annuity trusts, with these trust-related shifts characterized as changes in the form of beneficial ownership without a change in pecuniary interest under Rule 16a-13.
Positive
- None.
Negative
- None.
Insider Trade Summary 10b5-1
Exercise and Sale: 82,500 shares ($1.80M approx. pre-tax spread)
Exercise and Sale
7 txns
Insider
Hawkins Matthew J.
Role
Chief Executive Officer
Sold
82,500 shs ($2.14M)
Approx. gross sale proceeds
$2.14M
Approx. exercise cost
$342K
Approx. pre-tax spread
$1.80M
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Stock Options (right to buy) F5 | 82,500 | $0.00 | $0.00 |
| Exercise | Common Stock F2, F3 | 82,500 | $4.14 | $342K |
| Sale | Common Stock F4, F2, F3 | 82,500 | $25.9707 | $2.14M |
| Tax Withholding | Common Stock F1, F2 | 30,287 | $25.73 | $779K |
| holding | Stock Options (right to buy) F5, F6 | -- | -- | -- |
| holding | Stock Options (right to buy) F5, F6 | -- | -- | -- |
| holding | Stock Options (right to buy) F5 | -- | -- | -- |
Holdings After Transaction:
Stock Options (right to buy) — 3,020,196 contracts for 1,592,598 underlying shares (Direct);
Common Stock — 1,804,794 shares (Direct);
Stock Options (right to buy) — 66,374 contracts (Indirect, By 2024 grantor retained annuity trust);
Stock Options (right to buy) — 46,208 contracts (Indirect, By 2025 grantor retained annuity trust)
Footnotes (6)
- F1. The transaction represents shares of common stock withheld to pay taxes upon vesting of restricted stock units (RSUs) granted to the Reporting Person on April 1, 2025. The number of shares withheld was determined based on the actual sale price of shares sold on September 1, 2026 pursuant to a "sell-to-cover" transaction. The vesting schedule for this RSU grant, as originally reported on the Reporting Person's prior Form 4, was modified by the Talent & Compensation Committee. The original vesting schedule provided for 40% vesting on the third anniversary of the Vesting Commencement Date and 60% vesting on the fourth anniversary of the Vesting Commencement Date. The modified vesting schedule provides for 25% vesting on September 1, 2026, and 25% vesting on each of the second, third, and fourth anniversaries of the Vesting Commencement Date.
- F2. Includes unvested RSUs.
- F3. These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on March 13, 2026 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).
- F4. 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 $25.51 to $26.51, 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.
- F5. These options are currently vested.
- F6. Reflects annuity payments resulting in a change in the form of beneficial ownership (direct and trust holdings) without a change in pecuniary interest, exempt under Rule 16a-13.
Key Figures
Options exercised: 82,500 shares
Option exercise price: $4.14 per share
Shares sold: 82,500 shares
+5 more
8 metrics
Options exercised
82,500 shares
Stock options exercised into Waystar common stock on September 2, 2026
Option exercise price
$4.14 per share
Exercise price of stock options converted on September 2, 2026
Shares sold
82,500 shares
Waystar common shares sold on September 2, 2026
Weighted average sale price
$25.9707 per share
Weighted average price for 82,500 shares sold on September 2, 2026
Tax-withholding shares
30,287 shares
Shares withheld to pay RSU tax liability on September 1, 2026
Tax-withholding price
$25.73 per share
Price used for RSU tax-withholding shares on September 1, 2026
Direct option underlying shares
1,592,598 shares
Underlying Waystar common stock for vested options held directly, exercise price $4.14, expiring November 1, 2027
Indirect option underlying shares
66,374 and 46,208 shares
Underlying Waystar common stock for options held via 2024 and 2025 grantor retained annuity trusts
Key Terms
Rule 10b5-1(c), restricted stock units (RSUs), grantor retained annuity trust, sell-to-cover, +1 more
5 terms
Rule 10b5-1(c) regulatory
"plan adopted by the Reporting Person on March 13, 2026 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c)"
Rule 10b5-1(c) is an SEC guideline that lets company insiders set up a written, pre-planned schedule to buy or sell their company stock when they are not in possession of material, nonpublic information. For investors, it matters because such plans can reduce the appearance of insider trading by separating decisions from inside knowledge—like putting your trades on autopilot—while also requiring scrutiny since pre-planned trades can still affect market confidence and share value.
restricted stock units (RSUs) financial
"shares of common stock withheld to pay taxes upon vesting of restricted stock units (RSUs) granted"
Restricted stock units (RSUs) are a type of company promise to give employees shares of stock in the future, usually after certain conditions like working for a set time. They are like a gift promised today that you receive later, which can become valuable if the company's stock price goes up. RSUs matter because they are a way companies reward employees and can be a significant part of compensation.
grantor retained annuity trust financial
"By 2024 grantor retained annuity trust"
A grantor retained annuity trust (GRAT) is an estate-planning tool where the person who creates the trust transfers assets into it but receives fixed cash payments (an annuity) from the trust for a set number of years; whatever remains after that term passes to designated beneficiaries. It matters to investors because it can shift future appreciation of assets out of the creator’s taxable estate—like putting an asset into a timed vending machine that pays you fixed amounts while any extra value that grows inside the machine goes to heirs with reduced gift or estate tax consequences.
sell-to-cover financial
"determined based on the actual sale price of shares sold on September 1, 2026 pursuant to a "sell-to-cover" transaction"
Sell-to-cover is when part of newly issued or exercised company stock is immediately sold to pay required taxes and fees, so the recipient keeps the remaining shares. For investors this matters because it reduces the number of shares insiders or employees actually hold after a grant, can create small, routine share sales that aren’t signal of cashing out, and slightly increases share supply on the market—like selling a portion of a paycheck to cover the tax bill.
Rule 16a-13 regulatory
"change in the form of beneficial ownership (direct and trust holdings) without a change in pecuniary interest, exempt under Rule 16a-13"
FAQ
What did Waystar (WAY) CEO Matthew J. Hawkins report in this Form 4?
He exercised stock options for 82,500 shares of Waystar common stock at an exercise price of $4.14 per share and sold 82,500 shares at a weighted average price of $25.9707 per share on September 2, 2026.
Were the recent WAY insider transactions made under a Rule 10b5-1 plan?
Yes. The filing states that the reported transactions on Waystar common stock occurred automatically pursuant to a plan adopted by Matthew J. Hawkins on March 13, 2026 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).
What RSU vesting change did Waystar (WAY) disclose for the CEO?
The RSU grant to Matthew J. Hawkins now vests 25% on September 1, 2026 and 25% on each of the second, third, and fourth anniversaries of the vesting commencement date, replacing the prior 40%/60% third- and fourth-anniversary schedule.
What stock option holdings on Waystar (WAY) remain for the CEO after these transactions?
The filing shows vested stock options on Waystar common stock at an exercise price of $4.14 per share expiring on November 1, 2027, including positions tied to 1,592,598 underlying shares held directly and to 66,374 and 46,208 underlying shares held indirectly through 2024 and 2025 grantor retained annuity trusts.
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