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Joshua Henry has a long and varied work experience, beginning in 2004 as a High School English Teacher for Fairfax County Public Schools. In 2005, they became an Assistant Dean of Undergraduate Admission for the College of William and Mary. In 2008, they were a Graduate Intern at Harvard University, followed by a Graduate Assistant role at Boston College in 2009. In 2010, they joined Educational Advocates as an Associate, College Counseling. In 2011, they were an Assistant Director of Admission at Franklin W. Olin College of Engineering. From 2012 to 2017, they worked at Boston College - Wallace E. Carroll Graduate School of Management in roles as an Admissions and Marketing Consultant and Assistant Director of Graduate Admissions - Carroll School of Management. Since 2017, they have been employed by Technolutions as a Client Support Engineer and Senior Program Manager. In 2021, they joined RHB as Director of Technology Support and Training and Senior Technology Consultant.

Joshua Henry attended Boston College from 2008 to 2010, where they obtained a MA in Higher Education Administration. Joshua attended William & Mary from 1999 to 2003, where they obtained a BA in English and Secondary Education. In 2016, they obtained an Inbound Certification from HubSpot.