Dillon began his training at the Canton Ballet School under Cassandra Crowley. Throughout his training he attended such schools as American Ballet Theatre, Pittsburgh Ballet Theatre and Chautauqua Ballet. He also trained under Laura Alonso.

 Dillon joined the second company of the North Carolina Dance Theatre where he danced for two seasons. During that time he enjoyed working with and performing works of Alonso King and Mark Diamond. He then became a company member of the Dayton Ballet where his favorite roles included Hyde in Karen Russo-Burke's Jekyll and Hyde and Slugger in Christopher Fleming's Play Ball. After two seasons with the Dayton Ballet he joined the Western Ballet Theatre in Puerto Rico.