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Waystar (NYSE: WAY) CFO faces 12,583-share tax withholding after option vesting

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

Rhea-AI Filing Summary

Waystar Holding Corp. Chief Financial Officer Steven M. Oreskovich reported a routine tax-related share disposition. On the transaction date, 12,583 shares of common stock were withheld to cover taxes upon vesting of Non-Qualified Stock Options originally granted on June 6, 2024. The withheld shares were valued at $19.23 per share. After this tax-withholding disposition, Oreskovich directly owned 424,200 shares of Waystar common stock, a figure that the filing notes includes unvested RSUs.

Positive

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Insider Oreskovich Steven M
Role Chief Financial Officer
Type Security Shares Price Value
Tax Withholding Common Stock 12,583 $19.23 $242K
Holdings After Transaction: Common Stock — 424,200 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.
Shares withheld for taxes 12,583 shares Tax withholding on vesting Non-Qualified Stock Options
Per-share valuation $19.23 per share Value used to determine tax-withholding shares
Shares owned after transaction 424,200 shares Direct holdings following tax-withholding disposition; includes unvested RSUs
Tax-withholding shares count 12,583 shares Reported as taxWithholdingShares in transaction summary
Non-Qualified Stock Options financial
"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.
sell-to-cover transaction financial
"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.
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.
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*
Oreskovich Steven M
(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)
Director10% Owner
XOfficer (give title below)Other (specify below)
Chief Financial 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 Stock06/09/2026F12,583D$19.23424,200(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 insider transaction did Waystar (WAY) report for CFO Steven Oreskovich?

Waystar reported a tax-related share disposition by CFO Steven Oreskovich. The company withheld 12,583 common shares to pay taxes due on vesting Non-Qualified Stock Options granted on June 6, 2024, a standard mechanism rather than an open-market sale.

How many Waystar (WAY) shares were withheld for taxes in this Form 4?

The filing shows 12,583 Waystar common shares were withheld for taxes. These shares covered the tax obligation arising when previously granted Non-Qualified Stock Options vested, based on the actual sale price used in a related sell-to-cover transaction on June 9, 2026.

At what price were the withheld Waystar (WAY) shares valued in the tax transaction?

The withheld shares were valued at $19.23 per share. This value reflects the price used to determine how many shares were needed to satisfy tax obligations tied to vesting Non-Qualified Stock Options originally granted to the CFO on June 6, 2024.

How many Waystar (WAY) shares does CFO Steven Oreskovich hold after this transaction?

After the tax-withholding disposition, CFO Steven Oreskovich directly owned 424,200 Waystar common shares. The filing notes that this total includes unvested restricted stock units (RSUs), giving investors a clearer picture of his overall equity exposure to the company.

Was the Waystar (WAY) CFO’s Form 4 transaction an open-market sale?

No, the Form 4 describes a tax-withholding disposition, not an open-market sale. Shares were withheld to pay taxes on vesting Non-Qualified Stock Options, with the number of shares determined using the actual sale price from a separate sell-to-cover transaction.

What equity awards are referenced in the Waystar (WAY) CFO Form 4 filing?

The filing references Non-Qualified Stock Options granted on June 6, 2024, which vested and triggered the tax obligation. It also states that the CFO’s post-transaction holding of 424,200 shares includes unvested RSUs, indicating a mix of vested and unvested equity incentives.