[Form 4] Waystar Holding Corp. Insider Trading Activity

Rhea-AI Filing Summary

Waystar Holding Corp. insider transactions by Chief Business Officer Eric L. Sinclair III. The reporting person acquired 9,701 shares by exercising options at an exercise price of $4.14 and immediately acquired an equal number of underlying shares. The report also shows sale of 9,701 shares of common stock at a weighted-average price of $37.6343, executed across multiple transactions in a price range of $37.24 to $38.14. Following these transactions the reporting person beneficially owned 484,527 shares before the sale and 474,826 shares after. Some holdings include unvested RSUs and the option grants are currently vested. The acquisitions occurred pursuant to an internal plan intended to satisfy Rule 10b5-1(c) conditions.

Positive

• Exercise of vested options at a low exercise price ($4.14) demonstrates realized gain potential when sold at market prices
• Use of a Rule 10b5-1 plan provides procedural transparency and an affirmative defense for scheduled trades

Negative

• Reduction in direct beneficial ownership by 9,701 shares after the sale, which slightly decreases insider stake
• Sale executed across multiple prices may indicate partial liquidation rather than a single strategic transfer

Insights

Securities Analyst

TL;DR: Insider exercised low-cost options and sold the same number of shares at a much higher market price under a Rule 10b5-1 plan; routine liquidity action, not necessarily signal of company fundamentals.

The reporting shows an exercise of 9,701 options at $4.14 and contemporaneous sale of 9,701 shares at a weighted-average of $37.6343, with sales executed across a disclosed range. The transactions reduced the reporting person's direct beneficial ownership by 9,701 shares. The report references unvested RSUs as part of total beneficial holdings and indicates the exercise and sale occurred under an established plan intended to satisfy affirmative defense requirements of Rule 10b5-1(c).

Corporate Governance Expert

TL;DR: Insider used a pre-arranged trading plan to exercise vested options and sell shares; disclosure aligns with Section 16 reporting and Rule 10b5-1 mechanics.

The Form 4 discloses that the reporting person is an officer (Chief Business Officer) and that the transactions were automatic pursuant to a plan adopted earlier this year to satisfy Rule 10b5-1(c). The report also clarifies that options exercised were vested and that some beneficial holdings include unvested restricted stock units. The form includes the attorney-in-fact signature, consistent with delegation for filing.

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).

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)
09/22/2025

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	09/22/2025		M		9,701	A	$4.14	484,527(1)(2)	D
Common Stock	09/22/2025		S		9,701	D	$37.6343(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	09/22/2025		M			9,701	(4)	11/01/2027	Common Stock	9,701	$0	67,907	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 $37.24 to $38.14, 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	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 did Waystar (WAY) insider Eric L. Sinclair III do?

The officer exercised 9,701 stock options at $4.14 and sold 9,701 shares at a weighted-average price of $37.6343.

How many shares did the reporting person own after the transactions?

After the reported sale the filing shows beneficial ownership of 474,826 shares.

Were the options exercised vested and under what plan were trades executed?

The filing states the options were currently vested and the transactions occurred pursuant to a plan adopted to satisfy Rule 10b5-1(c) conditions.

At what prices were the shares sold?

Shares were sold in multiple transactions at prices ranging from $37.24 to $38.14, with a reported weighted-average sale price of $37.6343.

Do the reported holdings include unvested awards?

Yes; the filing notes that the total beneficial ownership figures include unvested restricted stock units (RSUs).