Waystar CEO Matthew J. Hawkins sells 82,500 shares

Q: How many shares did WAY CEO Matthew J. Hawkins sell?

Matthew J. Hawkins sold 82,500 common shares on October 6, 2026, at a weighted average price of $26.2287 per share; individual sale prices ranged from $25.98 to $26.60, inclusive. The sale occurred automatically under a Rule 10b5-1 plan adopted March 13, 2026.

Q: How many WAY stock options did Matthew J. Hawkins exercise?

He exercised options covering 82,500 shares at an exercise price of $4.14 per share on October 6, 2026. The related acquisition of common shares was reported as automatic under a Rule 10b5-1 plan adopted March 13, 2026.

The CEO's common-share acquisition and sale were automatic under a Rule 10b5-1 plan adopted March 13, 2026.

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Rhea-AI Filing Summary

Waystar Holding Corp. (WAY) Chief Executive Officer Matthew J. Hawkins exercised options covering 82,500 shares at an exercise price of $4.14 per share on October 6, 2026, and sold 82,500 common shares at a weighted average $26.2287 per share. The sale prices ranged from $25.98 to $26.60, inclusive.

The common-share acquisition and sale occurred automatically under a Rule 10b5-1 plan adopted March 13, 2026. Following the exercise, Hawkins reported 1,427,598 stock options directly, along with options covering 66,374 shares in a 2024 grantor retained annuity trust and 46,208 shares in a 2025 grantor retained annuity trust.

Insider Trade Summary 10b5-1

Exercise and Sale: 82,500 shares ($1.82M approx. pre-tax spread)

Exercise and Sale 5 txns

Insider Hawkins Matthew J.

Role Chief Executive Officer

Sold 82,500 shs ($2.16M)

Approx. gross sale proceeds $2.16M

Approx. exercise cost $342K

Approx. pre-tax spread $1.82M

Type	Security	Shares	Price	Value
Exercise	Stock Options (right to buy) ^F4	82,500	$0.00	$0.00
Exercise	Common Stock ^{F1, F2}	82,500	$4.14	$342K
Sale	Common Stock ^{F3, F1, F2}	82,500	$26.2287	$2.16M
holding	Stock Options (right to buy) ^F4	--	--	--
holding	Stock Options (right to buy) ^F4	--	--	--

Holdings After Transaction: Stock Options (right to buy) — 1,427,598 contracts (Direct); Common Stock — 1,804,794 shares (Direct); Stock Options (right to buy) — 66,374 contracts (Indirect, By 2024 grantor retained annuity trust); Stock Options (right to buy) — 46,208 contracts (Indirect, By 2025 grantor retained annuity trust)

Footnotes (4)

F1. Includes unvested RSUs.
F2. These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on March 13, 2026 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).
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 $25.98 to $26.60, 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.
F4. These options are currently vested.

Key Figures

Options exercised: 82,500 shares Exercise price: $4.14 per share Common shares sold: 82,500 shares +5 more

8 metrics

Options exercised 82,500 shares October 6, 2026

Exercise price $4.14 per share Options exercised October 6, 2026

Common shares sold 82,500 shares October 6, 2026

Weighted average sale price $26.2287 per share Sale on October 6, 2026

Sale price range $25.98 to $26.60 per share Inclusive range for the October 6, 2026 sale

Direct stock options reported following exercise 1,427,598 options Following the October 6, 2026 exercise

Options held through 2024 grantor retained annuity trust 66,374 underlying shares Indirect position reported October 6, 2026

Options held through 2025 grantor retained annuity trust 46,208 underlying shares Indirect position reported October 6, 2026

Key Terms

Rule 10b5-1(c), weighted average price, grantor retained annuity trust

3 terms

Rule 10b5-1(c) regulatory

"affirmative defense conditions of Rule 10b5-1(c)"

Rule 10b5-1(c) is an SEC guideline that lets company insiders set up a written, pre-planned schedule to buy or sell their company stock when they are not in possession of material, nonpublic information. For investors, it matters because such plans can reduce the appearance of insider trading by separating decisions from inside knowledge—like putting your trades on autopilot—while also requiring scrutiny since pre-planned trades can still affect market confidence and share value.

weighted average price financial

"The price reported in Column 4 is a weighted average price"

Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.

grantor retained annuity trust financial

"By 2024 grantor retained annuity trust"

A grantor retained annuity trust (GRAT) is an estate-planning tool where the person who creates the trust transfers assets into it but receives fixed cash payments (an annuity) from the trust for a set number of years; whatever remains after that term passes to designated beneficiaries. It matters to investors because it can shift future appreciation of assets out of the creator’s taxable estate—like putting an asset into a timed vending machine that pays you fixed amounts while any extra value that grows inside the machine goes to heirs with reduced gift or estate tax consequences.

FAQ

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

How many shares did WAY CEO Matthew J. Hawkins sell?

Matthew J. Hawkins sold 82,500 common shares on October 6, 2026, at a weighted average price of $26.2287 per share; individual sale prices ranged from $25.98 to $26.60, inclusive. The sale occurred automatically under a Rule 10b5-1 plan adopted March 13, 2026.

How many WAY stock options did Matthew J. Hawkins exercise?

He exercised options covering 82,500 shares at an exercise price of $4.14 per share on October 6, 2026. The related acquisition of common shares was reported as automatic under a Rule 10b5-1 plan adopted March 13, 2026.

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

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Available on EDGAR 10/07/2026 - 04:12 PM Accepted by SEC EDGAR 10/07/2026 - 04:12 PM

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).

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

UTAH

84043

(City)

(State)

(Zip)

UNITED STATES

(Country)

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
10/06/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock	10/06/2026		M		82,500	A	$4.14	1,887,294⁽¹⁾⁽²⁾	D
Common Stock	10/06/2026		S		82,500	D	$26.2287⁽³⁾	1,804,794⁽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)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Stock Options (right to buy)	$4.14	10/06/2026		M			82,500	⁽⁴⁾	11/01/2027	Common Stock	82,500	$0	1,427,598	D
Stock Options (right to buy)	$4.14							⁽⁴⁾	11/01/2027	Common Stock	66,374		66,374	I	By 2024 grantor retained annuity trust
Stock Options (right to buy)	$4.14							⁽⁴⁾	11/01/2027	Common Stock	46,208		46,208	I	By 2025 grantor retained annuity trust

Explanation of Responses:

1. Includes unvested RSUs.

2. These transactions occurred automatically pursuant to a plan adopted by the Reporting Person on March 13, 2026 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 $25.98 to $26.60, 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	10/07/2026
	** 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.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR