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Shira Cahn-Lipman has a diverse range of work experience primarily in the field of education and healthcare. Shira began their career as a Mental Health Specialist at the Franciscan Hospital for Children in 2005 before transitioning to roles such as After-School Theater Director/Educator at Ethical Culture Fieldston School and 5th-8th Grade Permanent Substitute Teacher at Farragut Middle School in 2006. In 2007, they worked as an Upper Elementary Classroom Educator at Cambridge Montessori School.

In 2008, they joined Planned Parenthood League of Massachusetts as the Manager of Youth Education and held this role until 2020. During their time there, they gained experience in managing and developing youth education programs. In 2020, they transitioned to Planned Parenthood Federation of America, where they initially held the position of Manager of Education Leadership, contributing to the strategic development of education programs. Currently, they serve as the Associate Director of Education Strategy, a role they have held since September 2022.

Overall, Shira Cahn-Lipman has demonstrated their commitment to education and healthcare throughout their career, taking on diverse roles and contributing to the advancement of these fields.

Shira Cahn-Lipman holds a Master's Degree in Creative Arts and Learning: Curriculum and Instruction from Lesley University, which they obtained from 2007 to 2010. Prior to that, they completed their undergraduate studies at Emerson College from 2001 to 2005, earning a Bachelor of Arts (B.A.) degree with a focus on Theatre/Theater.