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Robert Kosasky is the current Head of School & Academic Dean at St. Andrew’s Episcopal School. Robert has been in this role since 2002. Prior to that, they were the Upper School Director at Friends Select School from 1997 to 2002. Before that, they were the Assistant Head of School/Head of Upper School at The Rockland Country Day School from 1989 to 1997.

Kosasky's educational career began with a BA in Theirtory and Philosophy from Yale University. Robert then continued their education at Teachers College, Columbia University, where they received their MA in Education. Kosasky later returned to Teachers College to complete a Klingenstein Head of School Fellowship.

Aaron Hill - Head of Middle School, David Brown - Assistant Head of School & Academic Dean, and Lorraine Martinez Hanley - Director of Diversity, Equity & Inclusion report to Robert Kosasky.