Matthew J. Hawkins - 01 Sep 2026 Form 4 Insider Report for Waystar Holding Corp. (WAY)

Reporting relationship: Chief Executive Officer, Director
Issuer ticker: WAY
Reported as of: 01 Sep 2026
Net transaction value: -$2,142,583
SEC form: 4
Accepted by SEC: 03 Sep 2026, 13:15:15 UTC
Prior SEC filing: 13 Aug 2026
Source filing: View source filing
Reporting owner signature: /s/ Gregory R. Packer, as Attorney-in-Fact

Key filing fact

Matthew J. Hawkins filed Form 4 for Waystar Holding Corp. (WAY) on 03 Sep 2026.

Key facts

This page summarizes Matthew J. Hawkins's Form 4 filing for Waystar Holding Corp. (WAY).
4 reported transactions and 4 derivative rows are listed below.
Accepted by SEC: 03 Sep 2026, 13:15.

Change

Previous filing in this sequence was filed on 13 Aug 2026.
Current net transaction value: -$2,142,583.

Research use

This tells you what this filing adds before you inspect full transaction and derivative tables.
You can trace every row back to the original SEC filing document.

Evidence

Filed on Form 4

Ownership activity is grounded in SEC Form 4 disclosures.

View source filing

Reporting Owners (1)

CIK 0001998256 Primary reporting owner

Hawkins Matthew J.

Relationship: Chief Executive Officer, Director
Address: 1550 DIGITAL DRIVE, #300, LEHI
Signature: /s/ Gregory R. Packer, as Attorney-in-Fact
Signature date: 03 Sep 2026

Reported non-derivative transactions

Shares, units, or other non-derivative securities reported in this filing.

WAY transaction

Common Stock

Tax liability

Transaction value
Shares: -30,287
Change %: -1.7%
Price: $25.73^*
Shares after: 1,804,794
Date: 01 Sep 2026
Ownership: Direct
Footnotes: F1, F2

WAY transaction

Common Stock

Options Exercise

Transaction value
Shares: +82,500
Change %: +4.6%
Price: $4.14^*
Shares after: 1,887,294
Date: 02 Sep 2026
Ownership: Direct
Footnotes: F2, F3

WAY transaction

Common Stock

Sale

Transaction value: $2,142,583
Shares: -82,500
Change %: -4.4%
Price: $25.97
Shares after: 1,804,794
Date: 02 Sep 2026
Ownership: Direct
Footnotes: F2, F3, F4

Reported derivative securities

Options, warrants, convertible securities, or similar derivative positions disclosed in the filing.

WAY transaction Derivative

Stock Options (right to buy)

Options Exercise

Transaction value
Shares: -82,500
Change %: -5.2%
Price: $0.000000^*
Shares after: 1,510,098
Date: 02 Sep 2026
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 82,500
Exercise price: $4.14
Footnotes: F5

WAY holding Derivative

Stock Options (right to buy)

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 1,510,098
Date: 01 Sep 2026
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 1,592,598
Exercise price: $4.14
Footnotes: F5, F6

WAY holding Derivative

Stock Options (right to buy)

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 66,374
Date: 01 Sep 2026
Ownership: By 2024 grantor retained annuity trust
Underlying class: Common Stock
Underlying amount: 66,374
Exercise price: $4.14
Footnotes: F5, F6

WAY holding Derivative

Stock Options (right to buy)

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 46,208
Date: 01 Sep 2026
Ownership: By 2025 grantor retained annuity trust
Underlying class: Common Stock
Underlying amount: 46,208
Exercise price: $4.14
Footnotes: F5

^* marks a reported price that did not pass the local price check.

Additional SEC filing notes

Filing notes and footnotes

Rule 10b5-1 trading plan

These transactions were reported as open-market trades under a Rule 10b5-1 plan. The plan lets an insider set trading instructions in advance, which can reduce the risk of trading while in possession of material nonpublic information.

Original filing language: transaction made pursuant to a contract, instruction, or written plan intended to satisfy Rule 10b5-1(c).

Explanation of responses 6 footnotes

Footnote F1

The transaction represents shares of common stock withheld to pay taxes upon vesting of restricted stock units (RSUs) granted to the Reporting Person on April 1, 2025. The number of shares withheld was determined based on the actual sale price of shares sold on September 1, 2026 pursuant to a "sell-to-cover" transaction. The vesting schedule for this RSU grant, as originally reported on the Reporting Person's prior Form 4, was modified by the Talent & Compensation Committee. The original vesting schedule provided for 40% vesting on the third anniversary of the Vesting Commencement Date and 60% vesting on the fourth anniversary of the Vesting Commencement Date. The modified vesting schedule provides for 25% vesting on September 1, 2026, and 25% vesting on each of the second, third, and fourth anniversaries of the Vesting Commencement Date.

Footnote F2

Includes unvested RSUs.

Footnote F3

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).

Footnote F4

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 $25.51 to $26.51, 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.

Footnote F5

These options are currently vested.

Footnote F6

Reflects annuity payments resulting in a change in the form of beneficial ownership (direct and trust holdings) without a change in pecuniary interest, exempt under Rule 16a-13.