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Diane Oliveira currently serves as the Lower School Director at The Pegasus School, a position held since July 2022. Prior to this role, Diane was the Elementary School Principal at St. John's Episcopal Church and School from June 2020 to July 2022. Diane also gained leadership experience as the Middle School Director at Brentwood School between July 2016 and June 2020, and earlier at Good Shepherd Episcopal School as both Head of Middle School and Assistant Head of Middle School from July 2010 to June 2016. Diane holds a Master's degree in Educational Leadership from the University of New England, obtained in 2010, and a Bachelor of Applied Science in Kinesiology and Exercise Science from Springfield College, completed in 1988.