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Jim Wynn has worked in various roles throughout their career. Jim started in 2005 as an Assistant Vice President - Branch Manager at TCF Bank, where they worked until 2010. From 2010 to 2013, they worked at Associated Bank as a Relationship Manager and Sr. Branch Manager. In 2010, they also became a Board Member at North Metro Pediatrics. In 2013, they joined WESTconsin Credit Union as a Sr. Business Loan Officer, and later became the Vice President - Business Loans.

Jim Wynn completed their MBA with a finance emphasis at Hamline University from 2009 to 2011. Jim also earned a bachelor's degree in finance from St. Cloud State University between 2001 and 2005.