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Tobey Jackson has a diverse work experience in the education field. From 1998 to 2004, Tobey worked as a Teacher and Middle School Director at Boston Collegiate Charter School. Tobey then went on to become the Middle School Principal from 2004 to 2009. Tobey also worked for Match Education as the Chief Academic Officer from 2011 to 2016, followed by the role of Chief Talent Officer. In addition, Tobey was also a self-employed Educational Consultant from 2009 to 2011.

Tobey Jackson attended Brown University and obtained a Bachelor of Arts (B.A.) degree. Following that, Tobey attended the Harvard Graduate School of Education and earned a Master of Education (MEd) degree.