Kessler began his music industry career as a club DJ in 1977. He joined Tommy Boy as the director of A&R coordination in 1990 after stints as GM of Sanctuary Studios, New York from 1988-90 and Eastern Artists Recording Studio from 1986-88. He also held positions at New York's WKTU/K-ROCK.
For Tommy Boy, Kessler was involved in studio productions on Queen Latifah, Naughty By Nature, and Digital Underground, as well as the "Club MTV Party To Go" releases.