[Form 4] Waystar Holding Corp. Insider Trading Activity

Rhea-AI Filing Summary

Waystar Holding Corp. insider transactions by CFO Steven M. Oreskovich. On 06/06/2025 14,038 shares were withheld to satisfy taxes upon vesting of non‑qualified stock options, reported at a price of $40.55, leaving 354,512 shares beneficially owned. On 09/10/2025 the reporting person acquired 16,666 shares by exercising options at a $4.14 exercise price under a plan intended to satisfy Rule 10b5‑1, and on the same date sold 16,666 shares in multiple transactions at a weighted average price of $40.4925, returning beneficial ownership to 354,512 shares. The reporting person holds 101,205 stock options following these events. The filing discloses that the June 6, 2025 tax‑withholding transaction was not timely filed.

Positive

• Exercise at low strike: 16,666 options exercised at a $4.14 strike price, enabling potential value realization.
• Use of 10b5‑1 plan: September transactions occurred under a plan adopted 09/06/2024, indicating preplanned trading to mitigate timing concerns.
• Substantial option holdings remain: Reporting person retains 101,205 stock options, showing continued alignment with equity incentives.

Negative

• Late filing: The June 6, 2025 tax‑withholding transaction "was not timely filed," indicating a disclosure compliance lapse.
• Significant sale activity: Sale of 16,666 shares on 09/10/2025 reduced freely held shares, which may be viewed negatively by some investors.
• Tax withholding reduced share count: 14,038 shares withheld for taxes decreased beneficial ownership on 06/06/2025.

Insights

Financial Analyst

TL;DR: Insider exercised low strike options and sold shares at a significantly higher market price; transactions appear routine but include a late filing.

The reporting shows exercise of 16,666 options at a $4.14 strike with concurrent sales at a weighted average of $40.4925, indicating material insider liquidity realization. The report also documents withholding of 14,038 shares for taxes upon option vesting. Holding of 101,205 options remains significant. These actions are commonly used by executives to diversify or cover tax obligations; the filing notes a not timely filing for the June withholding, which raises a disclosure compliance issue but not necessarily a company operational concern.

Compliance / Risk Analyst

TL;DR: Transactions largely occurred pursuant to a 10b5‑1 plan, reducing insider timing risk, but a late report signals a compliance lapse.

The 09/10/2025 transactions are stated to have occurred automatically under a plan adopted 09/06/2024 intended to meet Rule 10b5‑1 affirmative defense conditions, which supports procedural compliance for scheduled trades. However, the disclosure that the 06/06/2025 tax‑withholding transaction "was not timely filed" is a clear procedural deficiency and could prompt follow‑up from compliance or regulators. No other regulatory or litigation items are disclosed in this Form 4.

SEC Form 4

FORM 4

UNITED 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).

X

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 UT 84043

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Waystar Holding Corp. [ WAY ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Financial Officer

3. Date of Earliest Transaction (Month/Day/Year)
06/06/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

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)
			Code	V	Amount	(A) or (D)	Price
Common Stock	06/06/2025		F		14,038	D	$40.55	354,512(1)	D
Common Stock	09/10/2025		M		16,666	A	$4.14	371,178(2)(3)	D
Common Stock	09/10/2025		S		16,666	D	$40.4925(4)	354,512(2)(3)	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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Stock Options (right to buy)	$4.14	09/10/2025		M			16,666	(5)	09/17/2028	Common Stock	16,666	$0	101,205	D

Explanation of Responses:

1. This transaction was not timely filed. 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 on June 6, 2025, based on the closing price of WAY common stock on that date.

2. Includes unvested RSUs.

3. These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on September 6, 2024 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).

4. 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 $40.09 to $40.90, 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.

5. These options are currently vested.

Remarks:

	/s/ Gregory R. Packer, as Attorney-in-Fact	09/11/2025
	** Signature of Reporting Person	Date
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.

FAQ

What transactions did Waystar (WAY) CFO Steven Oreskovich report on Form 4?

The Form 4 reports 14,038 shares withheldexercised 16,666 options$4.14sold 16,666 shares at a weighted average of $40.4925.

How many shares does the reporting person beneficially own after these transactions?

The filing reports beneficial ownership of 354,512 shares

Were the September 2025 transactions executed under a 10b5‑1 plan?

Yes. The filing states the September 10, 2025 transactions occurred automatically pursuant to a plan adopted on 09/06/2024 intended to satisfy the affirmative defense conditions of Rule 10b5‑1(c).

Did the Form 4 disclose any filing issues?

Yes. The filing explicitly states that the 06/06/2025 tax‑withholding transaction "was not timely filed."

How many stock options does Steven Oreskovich hold after these transactions?

The Form 4 indicates the reporting person beneficially owns 101,205 options