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Rob Oswald has a diverse work experience. Rob started their career at Home Depot in 1995 as a Department Supervisor in the Warehouse. Rob later moved on to become the Assistant Distribution Center Manager in 2000, and then the Distribution Center Manager in 2001. In 2003, they joined King Solutions as an Account Manager.

Rob Oswald attended Anoka Ramsey Community College from an unknown start date to 2003, where they studied General Education. Rob also studied in the Pre-Engineering curriculum at Macomb Community College, although the specific years are not provided. Additionally, Rob attended the University of Minnesota, College of Continuing Education, but no details regarding the degree or field of study are given.