Leonard started his career as an insurance professional in southeast Georgia more than 25 years ago. He is the former president of Blount, Burke, Wimberly and Hendricks Insurors in Statesboro, Georgia, serving with the firm from 1986-2011. Leonard was the co-owner and vice president of Paradigm Administrators, a third-party administration company headquartered in Atlanta, from 2001-2005. He then worked as a consultant for the insurance industry and large self-insured employers from 2005 until co-founding Capstone Benefits Consulting in 2012.
Leonard served as the president of the Independent Insurance Agents of Georgia from 1989-99. During his term as state president, the Georgia chapter received the highest national honor awarded by the Independent Insurance Agents and Brokers of America, the Best State Association Award, in 1998. Leonard is a graduate of the University of Georgia with a degree in business. He is active in numerous civic and charitable organizations, and is a resident of Statesboro, Georgia.