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Harry Huddleston has a diverse background in technical and managerial roles, primarily in the communications and electronics field. Harry started their career as a Radio Technician for NATO AFNORTH, where they maintained and repaired radio systems. Harry then joined the US Army, serving as a Maintenance Shop NCOIC and later as a Radio Technician for the Armed Forces Inauguration Committee. During their time at the White House Communications Agency, Harry held positions as a Technical Control Center Shift Lead and Wideband Radio Technician/Presidential Radio Team Lead, providing secure communications support to the President and other high-ranking officials. Harry also spent time at Airbus as a Secure Communications Network Field Service Engineer and later as a Secure Communications Technical Program Manager, overseeing program budget, sales, marketing, business development, and customer support. Throughout their career, Harry demonstrated strong technical skills, leadership abilities, and a commitment to ensuring effective communication capabilities.

Harry Huddleston's education history includes attending the University of Maryland Global Campus. The specific years, degree, and field of study are not provided. Additionally, Harry obtained a Top Secret SSBI/SCI with Yankee White certification from the United States Department of Defense in 2014.