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Dillon Overby has a diverse work experience starting with their role as a Sales Development Representative at Volunteer Basketball Coach in 2021. Dillon then worked as a Wellness Assistant at Kisco-Abbotswood at Irving Park from 2016 to 2022. In 2021, they also served as a Sales Development Representative at REVGEN. Currently, they are an Account Executive at UpKeep, where they previously held the positions of Business Development Representative and Sales Development Representative. Additionally, Dillon volunteered as a Basketball Coach at various organizations throughout their school tenure, including a local rec league and a middle school.

Dillon Overby pursued their education at the University of North Carolina at Greensboro from 2016 to 2020. During this time, they obtained a Bachelor's degree in Political Science and Government, as well as a Minor in Sports Coaching. In addition to their formal education, Dillon has also sought out additional certifications. In July 2021, they completed the "Filling the Funnel" certification from JB Sales. Furthermore, in November 2022, Dillon obtained the "Frictionless Sales" certification from HubSpot Academy.