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Robert Cooke has a diverse work experience in the education sector. Robert began their career as the Upper School Assistant Director at Mounds Park Academy in 2001 and later became the Middle School Director from 2003 to 2008. In 2008, they joined Brentwood School as the Upper School Director and held this role until 2015. Since 2015, they have been the Head of School at Community School.

Robert Cooke attended Carleton College from 1977 to 1981, where they obtained a Bachelor of Arts (B.A.) degree in History. Robert later pursued further education at Claremont Graduate University from 1985 to 1986, earning a Master of Arts (MA) degree in Education.