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Sean Wolfington has a diverse work experience, starting with their role as the Founder and Chairman of CarSaver, an auto buying platform that partners with Walmart. Sean also founded Data Driven Holdings, Team Velocity Marketing, and Tier10 Advertising, where they served as a Board Member. Additionally, they have been an investor in This Bar Saves Lives, an organization that provides nutrient packets to malnourished children. Wolfington has also served on the boards of Hispanicize, a digital and offline platform, and Automotive Leadership Roundtable. Sean was a board member for SOCIALDEALER, a company providing social media solutions for the automotive industry. Furthermore, they founded Offer Logix, a provider of automated pricing and payment data for online auto buying platforms, which was acquired in 2019. Lastly, they founded Car-Mercial, a digital marketing company for the automotive industry, which was acquired by DDH in 2018.

Sean Wolfington attended Harvard Business School Executive Education starting in 2016, where they are currently enrolled. Prior to that, they studied at Malvern Prepatory School from 1985 to 1989. Sean Wolfington also expressed an interest in business and studied in that field at Dickinson College, although specific dates for their time there are not provided.