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Richard Englebright has a diverse work experience spanning several industries. Richard started their career as an Electrician at Motor City Electric in 1973 and later worked at Englebright Electric Company and County Wide Electric Company in the same role. In 1989, they joined the Marion County Sheriff's Office as a Correctional Officer, before being promoted to Deputy and later to Sergeant in the Law Enforcement division. From 2005 to 2006, they served as a Sergeant and Law Enforcement Training Coordinator, responsible for coordinating and overseeing the training of law enforcement personnel. In 2007, they became a Lieutenant and Training Director, overseeing all agency training. In 2016, they worked as an Instructor at the College of Central Florida. Currently, they hold the position of Training Director at the Marion County Sheriff's Office.

Richard Englebright completed their Bachelor of Arts (BA) in Criminal Justice/Police Science from Saint Leo University from 2008 to 2010. Prior to that, they attended the Command Officer Management School at Saint Leo University in 2005. In addition to their formal education, Englebright also obtained multiple certifications including Taser Instructor from TASER International in July 2013, Third Party Commercial Driver License Tester from the State of Florida in June 2012, Colt M1911 Armorer from Colt Defense in March 2012, M16/M4/AR15 Armorer from Colt Defense in March 2012, Sig Sauer Pistol Armorer from Sig Sauer in February 2012. Richard also obtained the Florida CJSTC Driving Instructor certification in June 2008, Florida CJSTC Firearms Instructor certification in April 2007, Florida CJSTC Corrections Certificate in January 1990, and Florida CJSTC Law Enforcement Certificate in February 1989.