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Rob Stephenson began their work experience in 2005 at Knight Transportation, where they held the position of Operations until 2006. In 2006, they joined TCW as an Operations Manager and later became Terminal Manager in 2007. From 2012 to 2015, they served as Regional Manager - Eastern Terminals at TCW, and in 2015, they were promoted to the position of VP Eastern Region.

Rob Stephenson attended Parker College of Business at Georgia Southern University from 2000 to 2005, where they pursued a degree in Logistics. No specific field of study was mentioned.