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Jessica Reid has a diverse work history, starting with their role as a Military Intelligence Supervisor in the US Army from 2003 to 2009. Jessica then transitioned into the private sector and worked as the Operations Director and Owner of CrossFit Brick and Mortar from 2013 to 2014. In 2010, they became a History Teacher at Central Bucks School District and held this position until 2016. In 2016, they joined Team Red, White & Blue, where they took on various roles, including Program Manager, Area Director, and Associate Director of Operations - Volunteer Experience. Most recently, they have been working at the USO as the Regional Director of Operations for the Northeast region since 2023.

Jessica Reid earned a Bachelor's Degree in History and Anthropology from the University of Pennsylvania in the period of 1998 to 2002. Jessica later pursued a Master's Degree in Secondary Education and Teaching at the University of Pennsylvania from 2009 to 2010. Additionally, they hold certifications in Community Leadership Course for Veterans from Leadership Pittsburgh Inc. and CrossFit Level 2 from CrossFit, Inc.