As executive vice president and chief commercial officer, Michael DiSimone leads Convey’s centralized commercial organization, bringing together all business lines, product, marketing, and sales to deliver integrated strategies, deepen client focus, and accelerate growth. With over 30 years of experience in banking, HR consulting, benefits outsourcing, retirement administration, and healthcare reimbursement, he brings a strong track record of driving operational excellence and strategic growth.

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.