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David Chesher has a diversified work experience spanning over several companies. David started their career in 1996 as a Store Manager at GameStop. David then worked as a District Training Coordinator at CompUSA from 1997 to 2001. Afterward, they joined Data Systems International as a Personal Systems Specialist until 2003. In 2003, they joined Park University as a Technical Support Specialist and later took on roles as Lead Technical Support Specialist, Client Access and Campus Center Support Specialist, System Administrator, Manager of Technical Services, and Director Of Technical Services. Currently, they are serving as the Senior Director Of Technology at Park University. Additionally, they worked part-time as a QuizMaster at Geeks Who Drink from 2013 to 2015.

David Chesher attended Park University from 2016 to 2020, where they studied Business Administration and Management, General. Prior to that, they briefly attended the University of Missouri-Columbia in 1994-1995, where they studied Journalism.