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Charli Wessinger has held various positions throughout their work experience. Charli started their career at Full Sail University in 1998, where they served as the General Education Administrative Manager and later became a Course Director, overseeing lectures and assignments. In 2003, they worked as a Student Representative Department Manager at the same institution. Charli also worked as a Business Development Representative at Collegis from 2003 to 2004. From 2005 to 2008, they served as the Associate Dean of Rasmussen Online at Rasmussen College. In 2011, Charli ventured into entrepreneurship and became the Vice President of Operations and Co-Owner of Bear Creek Christmas Tree Farm. Charli also joined the Greater Chapin Community Foundation as a Board of Advisors member in 2013. In 2021, they took on the role of a Councilwoman for the County of Lexington, SC. Currently, Charli is the Director of Educational Technology at Newberry College, a position they have held since January 2022.

Charli Wessinger completed a Foundations of Digital Marketing Certificate from Rasmussen University in 2020. In 2016-2017, Charli pursued independent coursework at the University of West Georgia. In 2013, Charli received a certificate in Distance Education Certified Trainer from the University of West Georgia. In 2005, Charli earned a Distance Learner Leader Certificate from Nova Southeastern University, specializing in Distance/Online Learning. Charli also holds a Master of Arts (MA) degree in Management Administration of Educational Programs from Nova Southeastern University, obtained between 2003 and 2005. Charli's educational journey started at Newberry College where they earned a Bachelor of Arts (B.A.) in Theatre/Speech, graduating between 1989 and 1993.