Gregory has spent his career in theatre and music, first in Western Canada, and later in southern Ontario. He joined a cathedral choir at the age of 10, and since then has worked with a wide variety of ensembles and in a wide variety of roles, be that singer, accompanist, orchestra member or conductor. He has worked with chamber choirs and chamber orchestras, professional ensembles, university choirs and church choirs.
Gregory has a Bachelor of Music degree from McMaster University, and a Master of Sacred Music degree from Emmanuel College at the University of Toronto. He has been the organist of St. Andrew’s United Church in Brantford, Ontario since 2003.