[Form 4] Waystar Holding Corp. Insider Trading Activity

Rhea-AI Filing Summary

Matthew J. Hawkins, Chief Executive Officer and Director of Waystar Holding Corp. (WAY), reported multiple insider transactions. On 06/06/2025 he had 46,657 shares disposed at an average price of $40.55, resulting in reported beneficial ownership of 717,474 shares (which includes unvested RSUs). Subsequent automatic transactions under a plan intended to satisfy Rule 10b5-1 conditions show acquisitions of 12,200 and 12,800 shares on 09/22/2025 and 09/23/2025 at a $4.14 option price (with related sales at weighted average prices of about $38.08). The filing discloses holdings of exercisable stock options with a $4.14 exercise price and additional equity held indirectly through two grantor retained annuity trusts totaling 593,135 options reported indirectly.

Positive

• Substantial insider ownership retained: Reporting person continues to hold 717,474 shares directly, indicating alignment with shareholders.
• Use of 10b5-1 plan: Subsequent sales and acquisitions on 09/22/2025 and 09/23/2025 were executed under a pre-established plan, reducing risk of opportunistic trading.
• Options largely vested: Options reported as currently vested and exercisable, showing realized commitment through option exercise activity.

Negative

• Late reporting: The filing discloses the 06/06/2025 tax-withholding transaction was "not timely filed," which is a disclosure control lapse.
• Material disposals occurred: Disposal of 46,657 shares on 06/06/2025 reduced direct holdings and may be viewed as significant insider sells (though due to tax withholding).

Insights

Financial Analyst

TL;DR: Routine insider option exercises and sales under a pre-established trading plan; current direct holding remains material.

The filing documents standard executive equity activity: tax-withholding share disposals tied to option vesting, exercises at a $4.14 strike, and contemporaneous market sales executed under an affirmative 10b5-1 plan on 09/22/2025 and 09/23/2025. The reporting person still holds 717,474 shares directly, plus significant option positions and indirect trust holdings, which maintain substantial insider ownership alignment with shareholders. The late filing note for the June 6, 2025 withholding is disclosed but the explanatory footnote clarifies the reason.

Corporate Governance Expert

TL;DR: Transactions appear governed by pre-set plans and include standard tax-withholding mechanics; timely disclosure issues were noted.

The report shows use of a 10b5-1 trading plan to effect share sales and option exercises, which is common for executives to manage legal risk. However, the form discloses one transaction was "not timely filed," specifying shares withheld for taxes on vested options. Although the filing provides explanatory detail and current balances, the late reporting item is a governance point investors may review in the companys disclosure controls context.

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
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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).

1. Name and Address of Reporting Person^*

Hawkins Matthew J.

(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)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Executive 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		46,657	D	$40.55	717,474(1)(2)	D
Common Stock	09/22/2025		M		12,200	A	$4.14	729,674(1)(3)	D
Common Stock	09/22/2025		S		12,200	D	$38.0792(4)	717,474(1)(3)	D
Common Stock	09/23/2025		M		12,800	A	$4.14	730,274(1)(3)	D
Common Stock	09/23/2025		S		12,800	D	$38.0789(5)	717,474	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	09/22/2025		M			12,200	(6)	11/01/2027	Common Stock	12,200	$0	1,277,545	D
Stock Options (right to buy)	$4.14	09/23/2025		M			12,800	(6)	11/01/2027	Common Stock	12,800	$0	1,264,745	D
Stock Options (right to buy)	$4.14							(6)	11/01/2027	Common Stock	343,135		343,135	I	By 2024 grantor retained annuity trust
Stock Options (right to buy)	$4.14							(6)	11/01/2027	Common Stock	250,000		250,000	I	By 2025 grantor retained annuity trust

Explanation of Responses:

1. Includes unvested RSUs.

2. 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. The ending balance reported herein is accurate and reflects the Reporting Person's current holdings.

3. These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on June 6, 2025 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 $38.00 to $38.20, 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. 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 $38.00 to $38.16, 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.

6. These options are currently vested.

Remarks:

	/s/ Gregory R. Packer, as Attorney-in-Fact	09/24/2025
	** 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 trades did WAY CEO Matthew J. Hawkins report?

The filing reports a 46,657-share disposal on 06/06/2025 at $40.55 (tax withholding) and automatic acquisitions and sales on 09/22/2025 and 09/23/2025 (12,200 and 12,800 shares respectively) tied to option activity and a 10b5-1 plan.

How many Waystar (WAY) shares does Hawkins beneficially own after these transactions?

The report lists 717,474 shares beneficially owned following the reported transactions (including unvested RSUs).

Were any option exercises disclosed in the Form 4 for WAY?

Yes. The filing shows stock options with a $4.14 exercise price and multiple option-related transactions (including acquisitions of 12,200 and 12,800 shares) and sizable indirect option holdings through grantor retained annuity trusts.

Why were some shares disposed on 06/06/2025?

The filing states those 46,657 shares were withheld to pay taxes upon vesting of Non-Qualified Stock Options granted on June 6, 2024; the transaction was noted as not timely filed.

Were the 09/22/2025 and 09/23/2025 transactions part of a trading plan?

Yes. Footnotes state those transactions occurred automatically pursuant to a plan adopted on 06/06/2025 intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).