Dillard's teaching career began at Yanceyville School in 1930, where he became principal in 1932. At the time, Caswell County lacked a high school for African American students. Dillard extended the school's curriculum, allowing students to reach the 11th grade in 1933. This initiative led to the establishment of
Caswell County Training School (CCTS) in 1934. As principal of CCTS, Dillard advocated for improved facilities and resources. His efforts paid off in 1951 with the construction of a new three-story brick school building, following the issuance of school bonds in 1950. ==Legacy==