[Form 4] Waystar Holding Corp. Insider Trading Activity

Rhea-AI Filing Summary

Waystar Holding Corp. director and Chief Executive Officer Matthew J. Hawkins exercised vested stock options and sold the same shares under a pre-established Rule 10b5-1 trading plan adopted November 22, 2024. On 08/12/2025 he exercised options at an exercise price of $4.14 to acquire 46,667 shares and sold 46,667 shares in multiple transactions at a weighted average price of $34.6622 (range $34.44–$34.89 as disclosed).

Following these transactions the reporting person directly beneficially owned 764,131 shares. The filing also shows direct beneficial ownership of 1,289,745 stock options and indirect option holdings of 343,135 and 250,000 via grantor retained annuity trusts. The transactions are reported as occurring automatically pursuant to the 10b5-1 plan and the options involved were noted as vested.

Positive

• Transactions executed under a pre-established Rule 10b5-1 plan, adopted November 22, 2024, indicating pre-planned trading activity.
• Options were reported as vested, allowing lawful exercise and immediate disposition as disclosed.

Negative

• Director/CEO sold 46,667 shares, which reduced his direct beneficial ownership from 810,798 to 764,131 shares as shown on the form.
• Insider sale is material to insider liquidity (exercise at $4.14 and sale at weighted average $34.6622), which may be interpreted by some investors as cashing gains.

Insights

Securities Analyst

TL;DR: CEO exercised vested options at $4.14 and sold 46,667 shares at a weighted average of $34.6622 under a 10b5-1 plan.

The activity is a routine insider option exercise followed by an immediate planned sale, consistent with a Rule 10b5-1 program adopted on November 22, 2024. The exercise price of $4.14 versus the weighted average sale price of $34.6622 shows a large per-share gain on the exercised options; the filing reports the exact sale price range. This disclosure is procedural and provides transparency about timing and pricing of the transactions.

Impact assessment: Neutral for immediate valuation; informational for share-count and insider liquidity analysis.

Corporate Governance Expert

TL;DR: Transactions were executed under a pre-established, documented 10b5-1 plan and options stated as vested; reporting is compliant and transparent.

The filer discloses that the sales were made pursuant to an affirmative defense plan, and the form specifies that the options were vested. The filing also itemizes direct and indirect beneficial option holdings, including amounts held in grantor retained annuity trusts. From a governance perspective, use of a documented plan reduces questions about opportunistic timing, and clear reporting of holdings and transaction prices supports regulatory compliance and market transparency.

Impact assessment: Not materially impactful to corporate governance beyond routine insider liquidity disclosure.

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^*

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)
08/12/2025

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	08/12/2025		M		46,667	A	$4.14	810,798(1)	D
Common Stock	08/12/2025		S		46,667	D	$34.6622(2)	764,131(1)	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	08/12/2025		M			46,667	(3)	11/01/2027	Common Stock	46,667	$0	1,289,745	D
Stock Options (right to buy)	$4.14							(3)	11/01/2027	Common Stock	343,135		343,135	I	By 2024 grantor retained annuity trust
Stock Options (right to buy)	$4.14							(3)	11/01/2027	Common Stock	250,000		250,000	I	By 2025 grantor retained annuity trust

Explanation of Responses:

1. These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on November 22, 2024 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).

2. 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 $34.44 to $34.89, 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.

3. These options are currently vested.

Remarks:

	/s/ Gregory R. Packer, as Attorney-in-Fact	08/12/2025
	** 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 did Waystar (WAY) insider Matthew J. Hawkins do on 08/12/2025?

On 08/12/2025 he exercised vested options at an exercise price of $4.14 to acquire 46,667 shares and sold 46,667 shares at a weighted average price of $34.6622 under a 10b5-1 plan.

How many Waystar shares does Matthew J. Hawkins directly beneficially own after these transactions?

The filing reports he directly beneficially owned 764,131 shares following the reported transactions.

Were the sales part of a pre-arranged trading plan?

Yes. The transactions were disclosed as occurring automatically pursuant to a Rule 10b5-1 plan adopted on November 22, 2024.

What option and derivative holdings are disclosed for the reporting person?

The filing shows direct beneficial ownership of 1,289,745 stock options and indirect holdings of 343,135 and 250,000 options via grantor retained annuity trusts.

What price range were the sold shares executed at?

The shares were sold in multiple transactions at prices ranging from $34.44 to $34.89, with a weighted average sale price of $34.6622.