[Form 4] Waystar Holding Corp. Insider Trading Activity

Rhea-AI Filing Summary

Eric L. (Ric) Sinclair III, Chief Business Officer of Waystar Holding Corp. (WAY), reported transactions dated 08/20/2025 under a Rule 10b5-1 plan adopted February 19, 2025. He exercised 9,702 stock options with a $4.14 exercise price, adding 9,702 shares and increasing beneficial ownership to 500,572 shares (includes unvested RSUs). He then sold 9,702 shares in multiple trades at a weighted average price of $35.111, reducing beneficial ownership to 490,870 shares. The exercised options are vested and total options underlying common stock held after the transaction equal 9,702 (97,012 options outstanding direct). The Form 4 was signed by an attorney-in-fact on behalf of the reporting person.

Positive

• Exercise of options at $4.14 locked in a low-cost acquisition of shares
• Sales executed under a 10b5-1 plan, indicating transactions were preplanned
• Filing discloses weighted average sale price and includes note that full breakdown is available on request

Negative

• Net direct beneficial ownership declined from 500,572 to 490,870 shares after the sales
• Officer monetized shares, which may be viewed by some investors as reduced insider stake

Insights

Securities Analyst

TL;DR: Insider exercised low-cost options and sold an equal number of shares under a pre-established 10b5-1 plan, producing a sizeable realized gain per share.

The exercise at $4.14 followed by sales at a weighted average of $35.111 indicates the reporting person monetized appreciation from vested options. The transactions were executed under a 10b5-1 plan adopted February 19, 2025, which provides an affirmative defense to insider trading accusations when properly established. Net direct beneficial ownership declined from 500,572 to 490,870 shares after the sales. For investors, this is a routine liquidity event by an officer rather than evidence of a material change in company fundamentals.

Corporate Governance Expert

TL;DR: Use of a documented 10b5-1 plan and Attorney-in-Fact signature suggests procedural compliance and preplanned execution.

The filing discloses that the transactions occurred automatically under a plan intended to meet Rule 10b5-1(c) conditions, and the Reporting Person provided an attorney-in-fact signature. The disclosure of a weighted average sale price range and inclusion of unvested RSUs in beneficial ownership improve transparency. No amendment or other governance concerns 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^*

Sinclair III Eric L. (Ric)

(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 Business Officer

3. Date of Earliest Transaction (Month/Day/Year)
08/20/2025

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	08/20/2025		M		9,702	A	$4.14	500,572(1)(2)	D
Common Stock	08/20/2025		S		9,702	D	$35.111(3)	490,870(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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Stock Options (right to buy)	$4.14	08/20/2025		M			9,702	(4)	11/01/2027	Common Stock	9,702	$0	97,012	D

Explanation of Responses:

1. These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on February 19, 2025 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).

2. Includes unvested RSUs.

3. 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 $34.73 to $35.28, 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.

4. These options are currently vested.

Remarks:

	/s/ Gregory R. Packer, as Attorney-in-Fact	08/20/2025
	** 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 WAY insider Eric Sinclair report on 08/20/2025?

He exercised 9,702 options at a $4.14 exercise price and sold 9,702 shares at a weighted average price of $35.111 on 08/20/2025.

Was the sale of Waystar (WAY) shares part of a 10b5-1 trading plan?

Yes. The Form 4 states the transactions occurred automatically pursuant to a plan adopted on February 19, 2025 intended to satisfy Rule 10b5-1(c).

How did these transactions change Sinclair’s beneficial ownership of WAY?

Beneficial ownership increased to 500,572 shares after the option exercise and was reduced to 490,870 shares after the sales.

Are the exercised options vested and what are the option details?

Yes. The options exercised are currently vested; exercise price was $4.14, 9,702 options were exercised, and 97,012 options (total direct) are reported following the transaction.

Who signed the Form 4 filing for Eric Sinclair?

The Form 4 was signed on behalf of the reporting person by Gregory R. Packer, as Attorney-in-Fact on 08/20/2025.