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Tripp Wylie has a diverse range of work experience, starting with their current role as the Chief Transformation Officer at Crossroads. Prior to this, they served as the Chief of Staff, Director of Transformation, Manager of Strategic Initiatives, and Strategic Coordinator at the same company. Before joining Crossroads, Tripp worked at Lancaster Motor Company as the General Manager for eight years. Tripp was responsible for overseeing operations at the dealership and was also approved by General Motors to be a Dealer Successor.

Tripp Wylie attended the University of South Carolina Darla Moore School of Business, where they pursued a degree in Management with a field of study in Entrepreneurship. The duration of their education is not specified.