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Ray Leonard has extensive work experience in the insurance industry, primarily with Virginia Farm Bureau Mutual Insurance Company and Southern Farm Bureau Life Insurance Company. Ray began their career with Virginia Farm Bureau Mutual Insurance Company in 1991 as an Agent, and later took on roles as an Estate Planning Specialist and an Agency Manager. In 2004, they were promoted to Regional Sales Manager, a position they held until 2012. In 2013, Ray Leonard joined both Virginia Farm Bureau Mutual Insurance Company and Southern Farm Bureau Life Insurance Company as the Director of Sales, and later became the Vice President of Sales. In their current role, they report directly to the Executive Vice President/General Manager and Senior Vice President of Marketing, and is responsible for overseeing the sales and service activities of over 200 agents and managers in Virginia.

Ray Leonard attended Emory & Henry College from 1987 to 1991, where they earned a Bachelor of Arts degree in Business & Economics. From 1992 to 2004, they studied at The American College of Financial Services, obtaining the following certifications: CLU, ChFC, and LUTCF in the field of Financial Services. In 2003, Ray enrolled in the College for Financial Planning to pursue a CFP Certificant, although the end year of their studies is not provided.