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Gary McHenry spent 37 years in public education, starting as a counselor and retiring after serving as superintendent of three different school districts in 2012. During his career he served in the Ravenswood School District as a Counselor, in Mountain View Los Altos (MVLA) as Principal, in Oakland as an Area Superintendent, and in Stockton, Mt. Diablo and Inglewood as Superintendent. He started his career as an instructor at Foothill Community College and later taught in a Teacher Education program at John F. Kennedy University. He  earned his credential as a school psychologist in 1978.  After retirement he served as an alternative education instructor, and since 2018 as a coordinator of an Early College HS program in the MVLA District as well as a Leadership Coach at the University of California Berkeley, School of Education.

He joined the State Performance Plan Technical Assistance Project as a Technical Assistance (TA) Facilitator in the 2016-17 school year.  He has worked in 12 different school districts, serving as lead TA Facilitator in three.