Waystar CEO exercises options, sells 70,000 shares
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Form Type
4
Rhea-AI Filing Summary
Waystar Holding Corp. Chief Executive Officer Matthew J. Hawkins reported exercising stock options for 70,000 shares of common stock at $4.1400 per share and selling 70,000 shares in open-market transactions at weighted average prices of $23.0228 and $23.0873 in mid-July 2026.
The transactions occurred automatically under a Rule 10b5-1 trading plan adopted on March 13, 2026. Hawkins continues to hold common stock and vested stock options, including positions covering 1,468,337 underlying shares directly and 343,135 and 46,208 underlying shares through grantor retained annuity trusts.
Insider Trade Summary 10b5-1
Exercise and Sale: 70,000 shares ($1.32M approx. pre-tax spread)
Exercise and Sale
9 txns
Insider
Hawkins Matthew J.
Role
Chief Executive Officer
Sold
70,000 shs ($1.61M)
Approx. gross sale proceeds
$1.61M
Approx. exercise cost
$290K
Approx. pre-tax spread
$1.32M
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Stock Options (right to buy) F5 | 36,901 | $0.00 | $0.00 |
| Exercise | Common Stock F1, F2 | 36,901 | $4.14 | $153K |
| Sale | Common Stock F4, F1, F2 | 36,901 | $23.0873 | $852K |
| Exercise | Stock Options (right to buy) F5 | 33,099 | $0.00 | $0.00 |
| Exercise | Common Stock F1, F2 | 33,099 | $4.14 | $137K |
| Sale | Common Stock F3, F1, F2 | 33,099 | $23.0228 | $762K |
| holding | Stock Options (right to buy) F5, F6 | -- | -- | -- |
| holding | Stock Options (right to buy) F5 | -- | -- | -- |
| holding | Stock Options (right to buy) F5, F6 | -- | -- | -- |
Holdings After Transaction:
Stock Options (right to buy) — 2,866,674 contracts for 1,468,337 underlying shares (Direct);
Common Stock — 926,816 shares (Direct);
Stock Options (right to buy) — 343,135 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. Includes unvested RSUs.
- F2. 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).
- F3. 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 $23.00 to $23.08, 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.
- 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 $23.00 to $23.27, 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
Shares sold: 70000 shares
Shares exercised: 70000 shares
Weighted average sale price 2026-07-15: $23.0228 per share
+5 more
8 metrics
Shares sold
70000 shares
Aggregate common shares sold in July 15-16, 2026 open-market transactions
Shares exercised
70000 shares
Aggregate common shares acquired via stock option exercises coded "M"
Weighted average sale price 2026-07-15
$23.0228 per share
Common stock sale of 33099 shares on July 15, 2026
Weighted average sale price 2026-07-16
$23.0873 per share
Common stock sale of 36901 shares on July 16, 2026
Option exercise price
$4.1400 per share
Stock options (right to buy) into Waystar common stock
Direct options remaining
1468337 underlying shares
Direct stock options outstanding after reported exercises
2024 GRAT options
343135 underlying shares
Options held indirectly by 2024 grantor retained annuity trust
Rule 10b5-1 plan adoption date
March 13, 2026
Date Hawkins adopted trading plan covering these transactions
Key Terms
Rule 10b5-1(c), grantor retained annuity trust, Rule 16a-13, weighted average price, +1 more
5 terms
Rule 10b5-1(c) regulatory
"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.
grantor retained annuity trust financial
"By 2025 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.
Rule 16a-13 regulatory
"change in the form of beneficial ownership ... exempt under Rule 16a-13"
weighted average price financial
"The price reported in Column 4 is a weighted average price."
Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.
unvested RSUs financial
"Includes unvested RSUs."
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What insider transactions did Waystar (WAY) CEO Matthew J. Hawkins report?
Matthew J. Hawkins reported exercising 70,000 stock options at $4.1400 per share and selling 70,000 shares of Waystar common stock in open-market trades at weighted average prices of $23.0228 and $23.0873 during mid-July 2026.
What stock options did the Waystar (WAY) CEO exercise in July 2026?
He exercised stock options for 70,000 underlying shares of Waystar common stock at an exercise price of $4.1400 per share on July 15 and 16, 2026. The options are currently vested and carry an expiration date of November 1, 2027.
Were the Waystar (WAY) CEO’s trades made under a Rule 10b5-1 plan?
Yes. The filing notes these transactions occurred automatically under a trading plan adopted March 13, 2026 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c), and the Rule 10b5-1 checkbox is marked as applicable.
What Waystar (WAY) equity and option holdings remain after these transactions?
Individual rows report direct common stock holdings in the hundreds of thousands of shares, including unvested RSUs. Hawkins also retains vested stock options covering 1,468,337 underlying shares directly and 343,135 and 46,208 underlying shares through grantor retained annuity trusts.
How are trusts involved in the Waystar (WAY) CEO’s option holdings?
Some options are held indirectly through a 2024 grantor retained annuity trust and a 2025 grantor retained annuity trust, covering 343,135 and 46,208 underlying shares. A footnote explains related annuity payments changed the form of beneficial ownership without changing pecuniary interest under Rule 16a-13.
AI-generated analysis. How Rhea-AI works. Not financial advice.
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