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Chuck Paynter has an extensive work experience in the sales and education industry. Chuck currently serves as the Sales Director at ParentSquare since 2024. Previously, they worked as a Sales Director at Remind from 2018 to 2023, and also held the role of Regional Sales Manager - Northeast at Remind from 2018 to 2021. Before that, Chuck was the Regional Vice President of Sales at Agile Mind from 2013 to 2017. Chuck also served as the Vice President of Sales at Knowledge Delivery Systems, Inc in 2013. In addition, Chuck held various positions at K12 Inc., including Senior Director of Institutional Sales and School Development from 2005 to 2012, and Director of Marketing from 2001 to 2004. Chuck began their career as a Regional Director at Kaplan Inc. in 1993.

Chuck Paynter obtained a Master of Business Administration (MBA) degree from the University of Virginia Darden School of Business. Prior to that, they earned a Bachelor of Science (BS) degree in Geology and Biology from James Madison University. Additionally, they have obtained a certification in Foundations from Pragmatic Institute in 2021.