Michael DiSimone serves as the chief executive officer of Convey Health Solutions after previously serving as the company’s executive vice president and chief commercial officer, where he led the organization’s centralized commercial organization. A seasoned healthcare and financial services executive with over 30 years of experience, Michael has a strong track record of driving operational excellence and strategic growth across benefits outsourcing, healthcare reimbursement, retirement reimbursement, HR consulting, and banking. Since joining Convey in 2025, Michael has played a pivotal role in shaping the company’s commercial and operational capabilities, strengthening Convey’s ability to provide proven technology and analytics solutions that help health plan partners operate more effectively and efficiently.
Prior to Convey, Michael served as the chief operating officer for Inspira Financial, a leading provider of financial wellness solutions with more than five million clients holding over $56 billion in assets under custody while maintaining strong partnerships with employers, advisors, and institutions. When Inspira acquired PayFlex from CVS Health in 2022, Michael served as president and CEO.Under his leadership, PayFlex offered a robust suite of services, including Health Savings Accounts (HSAs), Flexible Spending Accounts (FSAs) for health care and dependent care, Health Reimbursement Arrangements (HRAs), commuter benefits, COBRA, and direct billing.
Michael has held leadership roles at Aetna, Mercer, JPMorgan Chase, Affiliated Computer Services, and Mellon Financial Corporation, where he managed large-scale global operations, HR service delivery, and financial strategies.
Michael earned a bachelor’s degree in accounting and an MBA in finance from Pace University–where he is currently a member of the board of trustees–and has completed executive education programs in general management and leadership at Columbia Business School. He currently resides in New York with his wife, Jennifer, of over 30 years, and has three children. He enjoys golf, fitness, and the theater, and spends most of his free time with the family.
