Coach Montgomery is a 2001 graduate of Cartersville high school, where he played football and baseball. He played baseball at Brewton Parker College before graduating from the University of Georgia in 2006 with a B.S. in Science Education. He coached baseball and football at Morgan County High School from 2006-2011, at North Paulding High School in 2011-2012, and Cartersville High School from 2012-2016.
Coach Montgomery was the Head Baseball Coach at Pepperell High School in 2016-17 before coming to woodland high school in 2017. Coach Montgomery is the 9th grade football coach and assistant baseball coach here at woodland. He and his wife, Latasha, have a daughter (Blair-9) and a son (Harper-6).