Under the mentorship of multi-emmy awarding winning composer, arranger, and conductor Ian Fraser, Montelione began learning the art of music direction. On the podium, Montelione was a semi-finalist and only American conductor in the Concours International pour Jeunes Chefs d’orchestres in Chenove, France and has conducted a number of groups including the Memphis Chamber Players, New Ballet Ensemble, West Point Military Academy Band, Falls Church Orchestra, UF Trumpet Ensemble, University of Southern California Chamber Winds, USC Brass Choir, USC Trumpet Ensemble, USC Chamber Winds, Rhodes College Orchestra, Florida Tech University Wind Ensemble, Jacksonville Civic Orchestra and the Capistrano Performing Arts Center Orchestra. As a music director, he has worked with Laura Bell Bundy, Lea Michelle, Bart Shatto, Steve Tewksbury, Eden Espinosa, and Adam Bartley. He spent many summers as music director for the Creede Repertory Theatre and the CRT Orchestra. He is a 2016 Henry Award Nominee for Best Music Director and Best Musical for his work with Guys and Dolls. He has also been music supervisor for Norwegian Cruise Lines and Royal Caribbean Cruise Lines preparing Broadway and production shows worldwide.