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Stephen Shellenbean has a varied work experience. Stephen began in 1997 as the Owner of Autumn Tree Productions, LLC, which provides historical education and entertainment. In 2000, they became a Business Solutions Manager, Quality Assurance Engineer, and Field Support Specialist at Crane Streamware. In 2001, they took on the role of Fight Director at the Vermont Renaissance Faire. In 2007, they became an Implementation Team Manager at Crane Merchandising Systems. From 2011 to 2016, they were the Owner of S3 Consulting, and from 2012 to 2019, they held various roles at VendScreen, including Customer Program Manager, Product Manager, and Customer Experience Manager. Since 2019, they have served as the Chief Operating Officer/Owner of Tentsmiths.

Stephen Shellenbean began their educational journey in 1988 at Young Harris College, where they earned an Associates in Science in Education. Stephen then attended The University of Georgia from 1990 to 1991, studying History. In 1991, Stephen transferred to Millersville University of Pennsylvania, where they continued their studies in History until 1992.