Craddock is a Lead Instructional Coach for Albemarle County Public Schools. Current responsibilities include Virtual Learning, Career and Technical Education, and Health and Physical Education. He is formerly the Career and Technical Education Lead Teacher at Monticello High School. Mr. Craddock taught Computer Science, Web Design, Microsoft IT Academy, and Economics and Personal Finance 
Mr. Craddock was the winner of the Red Apple Award in 2011 awarded by the Charlottesville Business Innovation Council and Outstanding Secondary Teacher of the Year awarded by UVA's Phi Delta Kappa Chapter.
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- Web. New Personal Finance Class in Albemarle County, Whitney Harris, NBC29, Charlottesville, VA, November 19, 2012, retrieved November 19, 2012.
- Web. CBIC 2011 Honorees, CBIC, Charlottesville, VA, retrieved July 25, 2013.