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Whitney Olson has held a number of positions since 2012. Whitney began their career as a Case Manager at Hoglund, Chwialkowski & Mrozik PLLC, where they completed appeals for clients that received Social Security denials and gathered medical evidence to support client claims. In 2014, they became a Business Office Assistant at Richfield Health Center, where they compiled financial files for admitting residents, worked with residents to complete necessary admission documents, and managed resident trust accounts. In 2015, they held two concurrent positions as an Administrative Assistant at Twin Cities Pain Clinic and Nokomis Health, Inc. Finally, from 2016 onward, they have been an Inventory Manager and Client Services Coordinator at Xvoucher.

Whitney Olson attended Northwood Technical College from 2005 to 2007, obtaining a degree in Medical Administrative Specialist.