Matt Sypek is currently the Music Director at Greenfield High School in Greenfield, Massachusetts, where he teaches band, chorus, and music electives. He attended Holyoke Community College and received an Associate of Arts degree in Music in 2008. Matt also holds a Bachelor of Music in Music Education (2012) and Master of Music in Wind Band Conducting (2016) from the University of Massachusetts. Matt was a Graduate Teaching Assistant with the University of Massachusetts Symphony Band, Wind Ensemble, and Athletic Bands.

Matt is in his sixth year teaching. Prior to teaching in Greenfield, he was the Band Director at Converse Middle School in Palmer, Massachusetts as well as Band Director at North Brookfield Junior–Senior High School in North Brookfield, Massachusetts. In addition to teaching, Matt stays active as a performer in The Valley Winds, as well as local community bands, church performances, and local musical theater productions. When not teaching or performing, he enjoys cooking, painting, writing and arranging music, and is a board and video game enthusiast. Matt currently resides in Palmer, Massachusetts.