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Stewart Reynolds has a long and varied work experience. Stewart began their career in 2004 as a Key Account Manager at UPS, where they worked their way up to become Director of Enterprise Accounts. In 2007, they became President/Owner of S&R Auto. In 2010, they became President/Owner of The Virginia Wine of the Month Club. In 2015, they began working as Industrial Authority Chairmen and Industrial Authority Board Member for Louisa County. In 2017, they became Managing Partner of Haymaker Auto. In 2020, they became Vice President of Business Development & Small Package Strategy for ConData and Director of Worldwide Sales for Slync.io. Most recently, in 2021, they joined HighlanderTek as Chief Revenue Officer (CRO) and Member of the Board of Advisors.

Stewart Reynolds received their Bachelor of Arts degree in History and Business Administration from the University of Virginia-Wise in 2004. Prior to that, they attended Louisa County High School from 1994 to 1998.