Michael began his education career two decades ago in community-service learning before working in charter school oversight for the Massachusetts Department of Education. He founded and ran the Project for School Innovation, a nonprofit that shared charter and district practices. In New York, Michael worked for the City Department of Education and New Visions for Public Schools as a leadership coach and transfer school specialist. In 2010, he founded Eskolta, a nonprofit that has worked with more than 50 New York City public schools to re-engage overage, under credited students by deeply transforming their experiences in schools.
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