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Reggie Jacobs has a diverse work experience in various companies. Reggie started their career as a PFC Manager at Wal-Mart in 1992. Then, they worked at Dollar General as a WMS Manager and later became the Manager of Distribution Systems, overseeing multiple DC operations and managing startups. In 1998, they joined Fred's Inc. where they held several roles including Director of Distribution Systems, Senior Vice President of Distribution and Transportation, and Executive Vice President Corporate Services, Distribution and Transportation. In 2015, Reggie became the Chief Operating Officer at Hill Country Holdings LLC before joining TruckPro, LLC as the Vice President of Distribution and Logistics.

Reggie Jacobs earned a Bachelor of Arts degree in Political Science from the University of Oklahoma in 1992. Prior to that, they studied PreLaw with a focus on Law/Political Science at Rose State College from 1988 to 1990. Reggie also completed their high school education.