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Sasha DeWind has a diverse work experience. Sasha started their career as a Dance Instructor at Berkeley Carroll Creative Arts Camp in 2001, and worked there until 2004. Following this, they became a Writing Fellow at Barnard College in 2004, and held this position until 2007. In 2007, they joined Tutor Associates as a Director, and later became the Vice President in 2013. Currently, they hold the position of CEO at Tutor Associates.

Sasha DeWind attended The Berkeley Carroll School for high school and completed their education in 2003. After that, Sasha pursued a Bachelor of Arts degree from Barnard College between the years 2003 and 2007. During their time at Barnard College, Sasha focused their studies on American Studies and 19th Century Literature.