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Jesse Crowding's work experience includes being a Head Teacher at Benchmark School starting in September 2014, a Co-Teacher at Benchmark School from September 2012 to August 2014, and a Support Teacher at Benchmark School from January 2012 to September 2012. Prior to that, they were a Student Teacher at Springfield Middle School from August 2011 to December 2011.

Jesse Crowding pursued a Bachelor of Science (B.S.) degree in Secondary Education with a focus on English and Communications from Penn State University, from 2007 to 2011. Later, from 2015 to 2019, Jesse attended West Chester University of Pennsylvania, where they obtained a Master of Education (MEd) degree in Reading.