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Craig Whitesell's work experience begins in 2010 when they started working as a Teacher at F&S Education until July 2013. From August 2013 to June 2016, they worked as a Tutor at MLS Educational Consultants, Inc. Starting in June 2016, Craig served as a Mathematics Teacher at Fairfax County Public Schools until September 2022. Currently, they are working as a Program Analyst at Systems Planning and Analysis, Inc., beginning in September 2022.

Craig Whitesell completed their Master's Degree in Secondary Education and Teaching from George Mason University from 2015 to 2019. Prior to that, they obtained a Bachelor of Science in Business Administration and Management, General from the University of Mary Washington from 2005 to 2009. In 2007, they briefly attended the University of Deusto, though the degree and field of study for that period are unspecified.