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Bobby Holt has worked in various roles throughout their career. Bobby began their professional journey as a Men's Basketball Manager at The University of Maryland from August 2008 to March 2011. Following this, they joined Maret School in July 2012 and took on the role of Director of Financial Aid and Associate Director of Admission. In this position, Bobby managed a large financial aid budget, utilized psychographic and demographic data to identify potential applicants, and analyzed admissions statistics. Bobby also served as an Assistant Basketball Coach at Maret School from April 2011 to July 2012.

Bobby Holt completed a Bachelor's degree in English Language and Literature from the University of Maryland from 2008 to 2011. In 2019 to 2020, they pursued a Master of Education (MEd) in School Leadership from the University of Pennsylvania Graduate School of Education.