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Katie Oberlander has a diverse range of work experience in the performing arts and education sectors. Katie is currently the Director of Community Engagement and Performing Arts at Harborlight Montessori School, a role they have held since September 2021. Prior to this, they were the Director of Performing Arts at the same school from September 2011 to July 2020. In July 2021, they joined Gloucester Stage Company as the Education Director, a position they held until July 2022. Katie also worked as a Long Term Substitute Middle School Drama Teacher at Miles River Middle School from October 2020 to August 2021. Earlier in their career, they served as a Performing Arts Instructor at YMCA of the North Shore from January 2006 to January 2013, and as a Theatre Director at Marblehead Community Charter Public School from 2010 to 2011. Katie began their career as a Drama Teacher at Norwood School from 1999 to 2005.

Katie Oberlander received their Bachelor of Music degree in Vocal Performance from the Eastman School of Music, where they studied from 1991 to 1995. Katie later pursued a Master of Arts (M.A.) degree in Theatre/Theatre Arts Management at American University. The specific start and end years for their studies at American University are not provided.