Mr. Bailey is a 1998 graduate of Surry County High School.  He earned his Bachelor of Science in Mathematics from Shaw University. Mr. Bailey graduated from Regent University with his Master's Degree in Education Administration and Supervision in December 2022. He started his career in public education in 2005 and taught middle school math until 2013.  He then joined Southampton High school until 2023, teaching high school mathematics. Mr. Bailey was promoted to high school assistant principal in fall 2023.