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Bobby Masterson has a diverse work experience in various roles and industries. Bobby started their career in 2002 as an Education Manager at Universal Technical Institute, where they worked until 2010. Following this, they joined A.T.I. Enterprises as the Director of Education from 2010 to 2011. In 2011, Bobby joined the City of Edmond, initially serving as the Fleet/Solid Waste Superintendent until 2022. Bobby then transitioned to the role of Assistant Director of Public Works, a position they currently hold.

Bobby Masterson pursued their education at the University of Phoenix from 2008 to 2010, where they earned a Bachelor's degree in Psychology.