Dillon makes his directorial debut with Watching Mr. Pearson. He is from Shelton, Connecticut. After earning a degree in Cinema and Literature from Boston University, Dillon moved to Amsterdam, Netherlands, where he worked at Storm Post Production as an assistant editor. His notable credits include Atlanta (Season 3), Steve McQueen's The Occupied City, and Netflix's Dirty Lines.

Dillon co-founded KT Pictures with lifelong friend Brian Reilly. Since its inception, KT Pictures has worked on multiple short films, three feature films, and an international web series. His first feature, Dilettantes, was made on a shoestring budget and distributed through BayView Entertainment. The series Play It By Ear, which Dillon helped write, produce, and edit, was accepted into the Nashville Film Festival, HollyShorts, Dances With Films, and Catalyst Content Festival.