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).