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Jesse Olson has a diverse work experience spanning over two decades. In 2000, Jesse began working as a Computer Analyst at Hormel Foods, where they stayed until 2006. Jesse then joined CR Bard as a Sr. Programmer/Analyst from 2006 to 2008. Later, Jesse returned to Hormel Foods and held various roles including Sr. Computer Analyst, Application Project Leader, Supervisor of Computer Analysts, and Manager of Applications. During their tenure at Hormel Foods, Jesse was involved in a significant Oracle ERP cloud transformation project, where they served as the IT technical director project role for all Oracle Fusion cloud integrations, cloud ops, and data conversions. Before joining the Wounded Warrior Project as a Business Applications Manager in 2023, Jesse pursued self-employment from 2021 to 2023.

Jesse Olson earned a Bachelor of Arts (BA) degree in Management Information Systems from Waldorf College. They attended the college from 1997 to 2000.