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Bobby Dickerson has a diverse work experience, starting in 2009 as a Personal Trainer at 24 Hour Fitness. From there, they completed an internship at Hawkins-Welwood Homes before joining the United States Marine Corps as a Sergeant from 2006 to 2014. Following their military service, they worked at Rogers-O'Brien Construction, initially as an Assistant Surveyor, then as a Project Engineer, Quality Manager, and currently as an Assistant Project Manager.

Bobby Dickerson attended Westlake High School from 2001 to 2005. Bobby did not obtain a degree or specialize in any field of study during their time at Westlake High School. In addition to their high school education, Bobby earned additional certifications. In March 2017, they obtained the FAA Part 107 Remote Pilot Operator License from the Federal Aviation Administration. Later, in August 2017, Bobby obtained the OSHA 30 hour certification from the OSHA Safety Training Institute.