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Deb Cunningham has had year of work experience as a Teacher Associate at the Center for Discovery, starting in August 2015. Prior to that, they worked at FROST VALLEY YMCA for several years in various roles including Healthcare tech (EMT-B) starting in February 2008, and as a Trip Leader, Enviromental Educator, and Day Camp Counselor from June 2002 to February 2008.

Deb Cunningham completed their Bachelor's degree in Outdoor Recreation from the State University of New York College at Cortland during the years 2000 to 2003. Following that, they pursued an Associate of Arts (AA) degree in Early Childhood Education and Teaching from Ulster County Community College from 2010 to 2012.