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Stephen Whitson has had a diverse work experience. Stephen started their career in the United States Air Force, where they served as a Colonel/Chief Programmer for over 30 years. After leaving the military, they joined WyoTech as the Regional Vice President of Operations for eight years. Whitson then moved on to Education Affiliates, where they served as the Campus President. In 2013, they retired and became a Gentleman Farmer and World Traveler.

Stephen Whitson obtained a Master's Degree in International Relations from Troy University in 1989-1990. Additionally, they pursued a Master's Degree in Vocational Education at Florida State University from 1979-1980.