Ryan Clegg

Ryan Clegg, President and CEO

Ryan Clegg

As President & CEO of Clegg Insurance Group, Ryan J. Clegg oversees all aspects of the agency and spearheads sales and production initiatives.

Ryan established Clegg Insurance Group in 2010. After experiencing significant growth in just a few years, the company acquired another insurance agency, adding a Safety Harbor location to the Clearwater, Florida-based Clegg Insurance Group.

Prior to establishing Clegg Insurance Group, Ryan was an Assistant Property Broker for Peachtree Special Risk Brokers, a subsidiary of the Brown & Brown insurance agency. Having worked on both the wholesale and retail sides of insurance, he has a unique understanding of how deals get done and brings this valuable perspective to his agency and clients.

In previous positions with Pinnacle Development and Franklin Templeton, Ryan also gained significant experience in commercial real estate, which laid the foundation for his expertise in commercial insurance lines.

As part of the Clegg Insurance Group team, Ryan enjoys company memberships in the National Insurance Agency Alliance and Strategic Agency Network of Florida.

Born and raised in Clearwater, Ryan has deep roots in the local community. He has served on the sales committee for The Copperheads, the membership committee for the Skip Cline Society/Morton Plant Foundation, and the Kettle Klassic Golf committee for the Salvation Army. He has also served as the Golf Chair of UPARC and Chair of Big Brothers Big Sisters’ Christmas in November annual fundraiser.

Ryan earned his bachelor’s degree in Business at Ohio University. He also holds the 2-20 General Lines (Property, Casualty, Surety, Marine, Health and Miscellaneous Lines) License. He is currently pursuing the Certified Insurance Counselor (CIC) designation.

Every day, Ryan brings his friendly and outgoing attitude and trustworthy demeanor to Clegg Insurance Group. The most rewarding aspects of his job are having the ability to save people money while adding value to their business or personal lives, and networking and being involved in the community.