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Waystar (WAY) CEO stock withheld to cover option tax bill

Filing Impact
(Very High)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Waystar Holding Corp. CEO Matthew J. Hawkins reported a routine tax-related share withholding. On the vesting of Non-Qualified Stock Options granted on June 6, 2024, 47,754 shares of common stock were withheld at $19.23 per share to cover tax obligations.

The Form 4 classifies this as a tax-withholding disposition, not an open-market trade. After this transaction, Hawkins directly holds 926,816 shares of Waystar common stock, which the disclosure notes includes unvested RSUs.

Positive

  • None.

Negative

  • None.
Insider Hawkins Matthew J.
Role Chief Executive Officer
Type Security Shares Price Value
Tax Withholding Common Stock 47,754 $19.23 $918K
Holdings After Transaction: Common Stock — 926,816 shares (Direct, null)
Footnotes (1)
  1. The transaction represents shares of common stock withheld to pay taxes upon vesting of Non-Qualified Stock Options granted to the Reporting Person on June 6, 2024. The number of shares withheld was determined based on the actual sale price of shares sold on June 9, 2026 pursuant to a sell-to-cover transaction. Includes unvested RSUs.
Tax-withheld shares 47,754 shares Shares withheld to pay taxes on option vesting
Withholding price $19.23 per share Value used to determine shares withheld
Shares held after transaction 926,816 shares Direct common stock holdings including unvested RSUs
Tax-withholding shares (summary) 47,754 shares Reported in transactionSummary as taxWithholdingShares
Dispose transactions 1 transaction Single tax-withholding disposition recorded
Non-Qualified Stock Options financial
"The transaction represents shares of common stock withheld to pay taxes upon vesting of Non-Qualified Stock Options granted to the Reporting Person on June 6, 2024."
Non-qualified stock options are a type of employee benefit that gives individuals the right to buy company shares at a set price, usually lower than the market value, within a certain period. Unlike other options that may have special tax advantages, these options are taxed as income when exercised, which can affect how much money the employee or investor ultimately gains. They are important because they can influence company compensation strategies and impact the financial outcomes for employees and investors.
RSUs financial
"Includes unvested RSUs."
RSUs, or restricted stock units, are a form of company shares given to employees as part of their compensation. They are typically awarded with certain restrictions, such as a waiting period before they can be fully owned or sold, similar to earning a gift that becomes fully yours over time. For investors, RSUs can impact a company's stock offerings and reflect how much the company relies on stock-based incentives to attract and retain talent.
sell-to-cover transaction financial
"The number of shares withheld was determined based on the actual sale price of shares sold on June 9, 2026 pursuant to a sell-to-cover transaction."
A sell-to-cover transaction is when a person granted company stock (for example as part of compensation or option exercise) immediately sells enough of those shares to pay required taxes or exercise costs and keeps the rest. Think of it like cashing part of a bonus to cover the tax bill; it provides necessary cash without the holder needing outside funds. Investors watch these sales because they increase trading volume and slightly reduce insider holdings, but they often reflect routine tax or cost management rather than a judgment on the company’s prospects.
tax-withholding disposition financial
"transaction_action: tax-withholding disposition"
A tax-withholding disposition is an event or transaction—such as selling or transferring securities, exercising options, or receiving compensation—that triggers a requirement to hold back part of the payment and remit it to tax authorities. It matters to investors because it reduces the cash they receive immediately and can change the timing and amount of taxable income, like a cashier taking a portion of your sale proceeds to pay taxes before you get the rest.
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Form 4 Insider Transactions: What Each Field Means →
SEC Form 4
FORM 4UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB APPROVAL
OMB Number:3235-0287
Estimated average burden
hours per response:0.5
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
1. Name and Address of Reporting Person*
Hawkins Matthew J.
(Last)(First)(Middle)
1550 DIGITAL DRIVE, #300
(Street)
LEHI UTAH 84043
(City)(State)(Zip)
UNITED STATES
(Country)		2. Issuer Name and Ticker or Trading Symbol
Waystar Holding Corp. [ WAY ] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
XDirector10% Owner
XOfficer (give title below)Other (specify below)
Chief Executive Officer
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
06/09/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year)2A. Deemed Execution Date, if any (Month/Day/Year)3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeVAmount(A) or (D)Price
Common Stock06/09/2026F47,754D$19.23926,816(1)(2)D
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year)3A. Deemed Execution Date, if any (Month/Day/Year)4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year)7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Explanation of Responses:
1. The transaction represents shares of common stock withheld to pay taxes upon vesting of Non-Qualified Stock Options granted to the Reporting Person on June 6, 2024. The number of shares withheld was determined based on the actual sale price of shares sold on June 9, 2026 pursuant to a sell-to-cover transaction.
2. Includes unvested RSUs.
Remarks:
/s/ Gregory R. Packer, as Attorney-in-Fact06/09/2026
** Signature of Reporting PersonDate
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

What did Waystar (WAY) CEO Matthew Hawkins report in this Form 4?

Waystar CEO Matthew J. Hawkins reported a tax-related share withholding, where 47,754 common shares were withheld to cover taxes upon option vesting. This is a mechanical disposition, not an open-market trade, and reflects standard equity compensation tax treatment.

How many Waystar shares were withheld for Matthew Hawkins’ tax obligations?

A total of 47,754 Waystar common shares were withheld to pay taxes tied to the vesting of Non-Qualified Stock Options granted on June 6, 2024. The withholding price was $19.23 per share, based on actual sale prices used in a sell-to-cover mechanism.

How many Waystar (WAY) shares does Matthew Hawkins hold after this transaction?

After the tax-withholding disposition, Matthew J. Hawkins directly holds 926,816 Waystar common shares. The filing notes this figure includes unvested restricted stock units (RSUs), giving investors a view of his ongoing equity stake following the tax event.

Was this Waystar CEO Form 4 an open-market stock sale?

No, this Form 4 does not reflect an open-market stock sale. It records a tax-withholding disposition, where shares were withheld to satisfy tax liabilities on vesting Non-Qualified Stock Options, determined using prices from a sell-to-cover transaction on June 9, 2026.

What triggered the tax withholding reported by Waystar CEO Matthew Hawkins?

The tax withholding was triggered by the vesting of Non-Qualified Stock Options granted to Matthew Hawkins on June 6, 2024. When these options vested, 47,754 shares were withheld to cover related tax obligations, as disclosed in the Form 4 footnotes.