Upon graduating high school, he enrolled at Lycoming College in Pennsylvania where he earned a dual degree in business administration and theater.

[2] Woodruff grew up a fan of films with monsters and creatures and created an interest in doing similar effects, working around the lack of materials in his city – in his own words, the only theatrical makeup supplies to be found was greasepaint at the back of a local pharmacy - such as using art class to create masks based on Planet of the Apes out of plaster bandages.

[2] He worked in a camera store while using his free time to visit studios seeking a job, and after six months he managed to become a make-up artist in the 1983 movie Metalstorm: The Destruction of Jared-Syn.

[6][7] This would soon be followed by Woodruff playing many creatures in the movie he did effects for, such as Gill-man in the 1987 comedy-action film The Monster Squad, the eponymous demon from Pumpkinhead, and the Alien.

The company soon became highly requested in Hollywood, with movies such as Alien 3, Death Becomes Her (both nominated for the Academy Award for Best Visual Effects, won by the latter), Demolition Man, Wolf and Starship Troopers.

[4] In the 2010s, Woodruff has continued to do practical effects in films such as Grown Ups 2, Ender's Game, Paul Blart: Mall Cop 2, Harbinger Down, Unnatural, It, Jurassic World: Fallen Kingdom and Godzilla: King of the Monsters.

In early 2017 Woodruff and his company Amalgamated Dynamics announced they would be creating and designing the cosmetics for Pennywise in the Andy Muschietti directed horror film It.

His contributions in this area were recognized by Muschietti after the film's release when he said "... without all the hard work from Tom, Alec and all the guys Pennywise wouldn't have had such a big impact on the audience that it did.