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Sheldon Henry has a diverse work experience, starting with their role as a Technology Director at St. John's Catholic Prep, where they managed the installation and maintenance of LAN systems, email systems, and websites. Sheldon then co-owned and managed a restaurant called Saladworks, overseeing all aspects of operations. Sheldon also worked as a Business Development Manager at VA Associates, where they developed relationships with government agencies and procured business. Sheldon further gained experience as a General Manager at Titlemax, responsible for store operations and profitability. Sheldon also worked as an Independent Agent at Aflac, creating new sales through networking and marketing. Sheldon served as the Director of Education Technology at St. Maria Goretti, developing technology curriculum and teaching various classes. Additionally, Sheldon worked as the IT Manager at Phoenix Health Center and as the Head Women's Basketball Coach at Frederick Community College. Most recently, they served as the Director of Information Technology at Friends Community School. Throughout their career, Sheldon has gained expertise in information technology, business development, management, and coaching.

Sheldon Henry earned their MBA degree in Technology and Finance from the University of the District of Columbia. Sheldon attended the university from 1989 to 1991. Prior to that, they completed their BA degree in Finance and Technology from Adelphi University, although the specific start and end years for this degree are not provided. In addition to their degrees, Sheldon obtained the ProHIPAA for Leaders certification in November 2018.