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Charlie Jo DeMay started their work experience in 2010 as a Promotions Intern at Peoria Chiefs. In 2012, they became a Technical Recruiter at Geneva Technical Services, where they worked until 2015. In 2015, Charlie joined GoHealth as a Corporate Recruiter and later became a Sales Team Lead starting in January 2021.

Charlie Jo DeMay attended Monmouth College from 2007 to 2011 where they earned a Bachelor of Arts degree in Public Relations.