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Jayson Winquist has a strong background in fitness and operations management. Jayson began their career in 2003 as the Director of Warehouse and Delivery Operations at LinPepCo. In 2008, they transitioned to the role of Group Fitness Instructor at the Norm Waitt Sr. YMCA, where they worked until 2015. From 2013 to 2016, they also served as a Group Fitness Instructor at the Four Seasons Health Club. In 2017, Jayson joined Top Tier Fit as a Group Fitness Instructor, a role they held until 2019. Most recently, in 2022, they became the owner of J&T Home Inspections LLC.

Jayson Winquist's education history begins with their high school education at North High School, where they studied from 1994 to 1998. After completing high school, they enrolled at the University of South Dakota in 2000 and studied English/Language Arts Teacher Education for the year 2000 to 2001.

In addition to their formal education, Jayson Winquist has obtained professional certifications. In April 2019, they became a Certified CrossFit Trainer (CCFT) through CrossFit, Inc. More recently, in March 2022, they obtained the Certified Residential Home Inspector (CRHI) certification from Inspection Certification Associates (ICA).