Raymond's first play, Fly South, was performed at the ‘91 Edinburgh Fringe Festival in Scotland, and won the Sommerville, MA Arts Council Award for Best New Work. His play, American Mouth premiered at the Kraine Theater in New York’s Fringe Festival in 2003. He collaborated with librettist David Bridel and composer Simon Gray on the musical comedy adaptation of Erdman's The Suicide, called The Glorious Death of Comrade What’s-His-Name. He also wrote sketches and songs for the New York-based comedy group, Mr. JumpyPants, of which he is a founding member. Currently he is a member of the Tony-honored BMI Musical Theatre Advanced Workshop. He won BMI's Harrington Award for Outstanding Creative Achievement in 2007.