Waystar Holding Corp.

During the three months ended June 30, 2026, none of our directors or officers adopted, modified, orterminated a “Rule 10b5-1 trading arrangement” or “non-Rule 10b5-1 trading arrangement” as each term is defined in Item 408 of Regulation S-K.

Appointment of Chief Financial Officer

The Company has appointed Alpana Wegner to serve as Chief Financial Officer of the Company, who commenced employment with the Company on July 27, 2026 and will assume responsibilities as the Company’s Principal Financial Officer effective August 1, 2026 (the "Effective Date").

Ms. Wegner, 54, brings more than 25 years of financial leadership experience, including as Chief Financial Officer of multiple publicly traded technology companies, to Waystar. She most recently served as Chief Financial Officer of Integral Ad Science Holding Corp., a global media measurement and optimization platform, from June 2025 to May 2026. Prior to that, Ms. Wegner served as Chief Financial Officer of SecureWorks Corp., a cybersecurity company, from June 2023 to February 2025. From April 2017 to May 2023, Ms. Wegner served in several positions at Benefitfocus, Inc., a cloud-based software solutions company, including Executive Vice President, Chief Financial Officer from August 2020 to May 2023. From October 2008 to January 2017, Ms. Wegner held senior positions at Blackbaud, Inc., a cloud computing provider. Ms. Wegner holds a Bachelor of Science in Accountancy from Arizona State University.

In connection with her appointment, the Company entered into an Employment Agreement with Ms. Wegner, dated as of the Effective Date (the "Employment Agreement"). Pursuant to the Employment Agreement, Ms. Wegner will receive an annual base salary of $500,000 and will be eligible for an annual incentive bonus with a target of 110% of her base salary, based on the achievement of Company and individual performance objectives as determined by the Compensation Committee of the Board. Ms. Wegner will also be eligible to receive a sign-on equity award under the Company's 2024 Equity Incentive Plan with a grant date value equal to $7,000,000, consisting of 50% restricted stock units and 50% performance stock units, subject to approval by the Compensation Committee. Ms. Wegner's employment agreement also provides for certain severance payments and benefits upon a qualifying termination, which payments and benefits are materially consistent with those provided to other executive officers of the Company and described in the Proxy Statement (as defined below), and contains customary restrictive covenants, including non-competition, non-solicitation, confidentiality, and mutual non-disparagement provisions.

There are no family relationships between Ms. Wegner and any Company director or executive officer, and no arrangements or understandings between Ms. Wegner and any other person pursuant to which she was selected as an officer. Ms. Wegner has no involvement in any legal proceedings that would require disclosure. Ms. Wegner is not a party to any current or proposed transaction with the Company for which disclosure is required under Item 404(a) of Regulation S-K.

The foregoing description of the Employment Agreement is qualified in its entirety by reference to the full text of the Employment Agreement, a copy of which is attached hereto as Exhibit 10.2 and incorporated herein by reference.

Departure of Chief Financial Officer

In connection with Ms. Wegner's appointment, the Company also announced the departure of Steven M. Oreskovich from his role as Chief Financial Officer of the Company, effective as of the Effective Date. Mr. Oreskovich will continue to support the Company in an advisory capacity as described below, and for purposes of his existing employment agreement with the Company, Mr. Oreskovich's departure is “without cause.”

In connection with his departure, the Company and Mr. Oreskovich have entered into a Separation and Release Agreement (the "Separation Agreement"), which confirms Mr. Oreskovich's severance benefits and post-termination obligations under his employment agreement. The severance benefits to be received by Mr. Oreskovich under the Separation Agreement, subject to his execution and non-revocation of a general release of claims and a reaffirmation release, are materially consistent with those described under the caption "Potential Payments Upon Termination or Change of Control" in connection with a termination without cause in the Company's Definitive Proxy Statement for its 2026 annual meeting of its stockholders, filed with the Securities and Exchange Commission on April 17, 2026 (the “Proxy Statement”), except that the Separation Agreement provides for up to eighteen (18) months of continued COBRA coverage in lieu of twelve (12) months as described in the Proxy Statement. The Separation Agreement also includes confidentiality obligations, a non-disparagement covenant, and cooperation obligations.

In addition, the Company and Mr. Oreskovich have entered into a Strategic Advisor Agreement (the "Advisory Agreement," included as an exhibit to the Separation Agreement), pursuant to which Mr. Oreskovich will provide strategic advisory services to the Company through June 15, 2027 (the "Consulting Period"). Under the Advisory Agreement, Mr. Oreskovich will serve as an independent contractor and will be entitled to receive aggregate compensation of $440,667, payable in equal monthly installments over the Consulting Period. Certain outstanding Company equity awards held by Mr. Oreskovich as of the Effective Date will continue to vest, or may accelerate, during the Consulting Period.

The foregoing descriptions of the Separation Agreement and the Advisory Agreement (included as an exhibit to the Separation Agreement) are qualified in their entirety by reference to the full text of the agreements, copies of which are attached hereto as Exhibit 10.3 and incorporated herein by reference.