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Dennis Stapleton has a vast range of work experience in the beverage industry. Dennis began their career at Flowers Foods & Subsidiaries as an Operations Manager in 1997. Dennis then moved on to Alabama Crown Distributing Co, where they worked as a Sales Supervisor from 1999 to 2001. Dennis joined Birmingham Beverage Company as an Impact Account Manager in 2001 before transitioning to Supreme Beverage Company as a Chain Account Manager, where they worked until 2007. Dennis then joined MillerCoors as a Chain Account Manager for a year and a half before becoming the Director of Sales at Health Med in 2009. Dennis then worked as a Key Account Manager at Cone Distributing, Inc. from 2010 to 2013. After that, they became a Field Sales Manager at United Brands Company until 2015. Dennis's most recent role has been as a Regional Sales Manager - Southeast at Geloso Beverage Group since July 2015.

Dennis Stapleton attended Jefferson State Community College from 1991 to 2003, where they studied Criminal Justice and Corrections. Following their time at Jefferson State, Dennis enrolled at American InterContinental University to pursue a degree in Marketing, although specific dates for this period of their education are not provided.