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Bailey Watkins has primarily worked in the logistics and therapy industries. In 2017, they served as an Assistant at Hoosier Freight and Warehousing. In 2021, they had an internship at Therapia Aventura, where they worked as a Project Manager. During their internship, Bailey created a Masters program for Outdoor Sports and worked on various therapeutic projects. The following year, in 2022, Bailey became the Director of National Accounts at Hanzo Logistics.

Bailey Watkins attended the University of Mississippi from 2018 to 2022, where they obtained a Bachelor's degree in Psychology.