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Jake Caudill has had a varied work experience. Starting in 2012, they worked as a Summer Worker for the Washington County Maintenance Department. In 2015, they were a Resident Advisor at Emory and Henry College and an Outdoor Trip Leader for the Emory & Henry College Outdoor Program. In 2016, they were a Summer Camp Counselor for the Emory and Henry College Summer Scholars Camp. In 2017, they were a GIS Intern for the Mount Rogers Planning District Commission and a Head Resident Advisor at Emory and Henry College. In 2018, they were a GIS Technician Intern for the Town Of Abingdon and a Summer Camp Counselor for the Emory and Henry College Summer Scholars Camp. Currently, they are a GIS Senior Project Manager for InteractiveGIS.

Jake Caudill attended Emory & Henry College from 2014 to 2018, where they obtained a degree in Environmental Studies, Geography and Civic Innovation. In 2016, they also attended Dublin City University for Humanities/Humanistic Studies.