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Jackson Wayland has a diverse work experience. Jackson worked as an Account Manager at INSUREtrust starting in 2022. Prior to that, they served as a Sports Referee at Cherokee Youth Basketball Association since November 2016. In this role, they coordinated basketball games for elementary and middle school students, ensuring order and structure while maintaining respectful communication with referees and coaches. Additionally, they worked as an Agent Team Member/Intern at Lee Dempsey State Farm Agency in 2021 and as a Summer Intern at Jan Rooney - State Farm Insurance Agent in 2020. Jackson also gained customer service experience as a Food Runner/Dishwasher at Duke's Bar and Grill in 2019, providing excellent service, familiarizing guests with the menu, and ensuring cleanliness in both the dining area and kitchen.

Jackson Wayland attended Creekview High School from 2014 to 2018 where they obtained their High School Diploma. After completing high school, they enrolled at Georgia College & State University in 2018 and graduated in 2020 with a degree in Management. During their time at Georgia College & State University, they focused on Business, Management, Marketing, and Related Support Services.

Following their undergraduate studies, Jackson pursued further education at the University of Georgia - Terry College of Business from 2020 to 2022. Jackson obtained their Bachelors degree in Risk Management during this period. Additionally, they acquired a certification as an Insurance Agent in Property & Casualty from the Georgia Department of Insurance & Safety Fire in June 2021.

At some point, Jackson also attended the University of Oxford, although specific details regarding the duration and degree obtained are not provided. However, it is known that their studies at Oxford included topics related to Globalization, Financial Leadership, Cybersecurity, and Medieval Literature.