Meet The Team

Tom Phelan, President and Chief Executive Officer

Thomas J. Phelan, CPA, is President and CEO of Chesapeake Employers’ Insurance Company, formerly IWIF. In this capacity, he is responsible for setting the vision for the organization, making strategic decisions, and is accountable for the organization’s financial results. Mr. Phelan reports to Chesapeake Employers’ nine-member Board of Directors. He was appointed President and CEO in April 2007. 

Prior to this, Mr. Phelan held the position of Chief Financial Officer and Executive Vice President of Finance. In this role, he was responsible for budgeting, forecasting, modeling, variance analysis, and reporting of financial results. In addition, Mr. Phelan oversaw the Underwriting, Loss Control, Premium Audit, and Information Systems departments. He joined the company in 1990 as Actuarial Coordinator and Internal Auditor. 

Board of Directors

We are headed by a nine-member Board of Directors appointed by the Governor for a maximum of two, five-year terms.

Suzanne Carter Thompson

Board Chair

Wayne Gioioso, Sr.

Vice Chair

V. Rocky Gonzalez


Leonard Schuler, Jr.


Franklin J. Hajek


Lewis C. Powell


Maria Tildon


Martin G. Madden