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Jena Sargent has a long work history, beginning in 2001 with Lake Minnetonka Clothing Co. as a Retail Manager, where they were responsible for opening and closing the store, cashier, inventory, and cleaning. Jena then moved to Caribou Coffee in 2003, where they were a Shift Supervisor responsible for opening and closing the store, inventory, and overseeing employees. In 2004, Jena worked as a Production Supervisor for Innov8, a temporary position created for the company's involvement in the Winter Olympics. Jena was responsible for scheduling production according to deadline, opening and closing shop, taking inventory, and giving input on packaging. In 2009, Jena returned to WhiteBoard Product Solutions as an Intern. Jena then moved up the ranks to Business Coordinator in 2010 and Business Manager in 2011, where they were responsible for business development and consistently looked for ways to make things better and more efficient. In 2011, Jena also worked as a Rock Wall Instructor for Lifetime Fitnesss.

Jena Sargent attended Minnetonka High School before completing a Bachelor of Arts in Economics at Colorado College from 2005 to 2009. Jena then attended National Outdoor Leadership School in 2010 and Outward Bound in 2003, both for Outdoor Education.