Waystar (WAY) insider exercises 9,701 options, sells 9,701 shares

Waystar Holding Corp. insider transaction: the company’s Chief Business Officer reported an option exercise and share sale.

Rhea-AI Filing Summary

Waystar Holding Corp. insider transaction: the company’s Chief Business Officer reported an option exercise and share sale. On 11/20/2025, the officer exercised stock options to acquire 9,701 shares of common stock at $4.14 per share and then sold 9,701 shares of common stock at a weighted average price of $35.2728 per share in multiple trades between $34.79 and $35.80. After these transactions, the officer beneficially owned 474,826 shares of common stock and 48,505 stock options. The filing notes that these trades occurred automatically under a Rule 10b5-1(c) trading plan adopted on February 19, 2025, and that the options exercised are fully vested and expire on 11/01/2027.

Insider Trade Summary

Exercise and Sale: 9,701 shares ($302K approx. pre-tax spread)

Exercise and Sale 3 txns

Insider Sinclair III Eric L. (Ric)

Role Chief Business Officer

Sold 9,701 shs ($342K)

Approx. gross sale proceeds $342K

Approx. exercise cost $40K

Approx. pre-tax spread $302K

Type	Security	Shares	Price	Value
Exercise	Stock Options (right to buy)	9,701	$0.00	$0.00
Exercise	Common Stock	9,701	$4.14	$40K
Sale	Common Stock	9,701	$35.2728	$342K

Holdings After Transaction: Stock Options (right to buy) — 48,505 contracts (Direct); Common Stock — 474,826 shares (Direct)

Footnotes (4)

1. F1. Includes unvested RSUs.
2. F2. 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).
3. 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 $34.79 to $35.80, 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. F4. These options are currently vested.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transaction did Waystar (WAY) report in this Form 4?

The Chief Business Officer of Waystar Holding Corp. (WAY) reported exercising 9,701 stock options and selling 9,701 shares of common stock on 11/20/2025.

At what prices were the Waystar (WAY) options exercised and shares sold?

The officer exercised options at $4.14 per share and sold 9,701 shares at a weighted average price of $35.2728, in trades ranging from $34.79 to $35.80.

How many Waystar (WAY) shares does the insider own after the transaction?

After the reported trades, the officer beneficially owned 474,826 shares of Waystar common stock and 48,505 stock options.

Was the Waystar (WAY) insider trade made under a Rule 10b5-1 plan?

Yes. The transactions occurred automatically under a Rule 10b5-1(c) trading plan adopted by the reporting person on February 19, 2025.

What is the status and expiration of the Waystar (WAY) stock options exercised?

The exercised stock options are reported as currently vested and carry an expiration date of 11/01/2027.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 11/21/2025 - 11:01 AM EST Learn about SEC filing dates

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)
11/20/2025

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	11/20/2025		M		9,701	A	$4.14	484,527(1)(2)	D
Common Stock	11/20/2025		S		9,701	D	$35.2728(3)	474,826(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	11/20/2025		M			9,701	(4)	11/01/2027	Common Stock	9,701	$0	48,505	D

Explanation of Responses:

1. Includes unvested RSUs.

2. 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).

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 $34.79 to $35.80, 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	11/21/2025
	** 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.