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Kendall Chester began their work experience in 2010 as a Manager of Teacher Leadership Development at Teach For America. They held this position from June 2010 until September 2012. In October 2012, they began working as the Director of Development at New Way Learning Academy, a position they still currently hold.

Kendall Chester received a Bachelor of Arts (B.A.) degree in Psychology from Arizona State University in the years 2004 to 2008. Following that, Kendall pursued further education at the same university and obtained a Master's degree in Special Education and Teaching from 2008 to 2010.