Blake Montgomery began his career in Chicago directing ensemble clown theater and performing with a variety of non-naturalistic Chicago theaters, most notably Redmoon with whom he collaborated for more than a decade.

In 2005, Montgomery founded The Building Stage, a theater company and performance space, where he served as Artistic Director until its closing in 2013. The company was known for its ensemble-devised, director-driven creations, particularly in literary adaptations like their Jeff Award-winning Moby-Dick and the poetic, clown-inspired Dawn, Quixote.

Montgomery's artistic approach draws on his training at the École Jacques Lecoq, the Dell'Arte School of Physical Theater, and Middlebury College. A member of Actors' Equity, his performances in Chicago include work with The House Theatre, The Hypocrites, Remy Bumppo Theatre Company, Court Theatre, Chicago Shakespeare, Steppenwolf, and Writers Theatre.