Montgomery was born and raised in Lawton and graduated from Eisenhower High School. He began college at Cameron University where he became involved in ROTC and student government. He then transferred to the University of Oklahoma receiving a bachelor’s in International Studies. While in college, he studied abroad in Brazil and studied Russian for two years.
He went on to work at Northwest Mutual and the governor’s office before getting elected to the House of Representatives in 2014. While in the House, he served as the Vice Chair of the Appropriations and Budget Finance Committee as well as a member of the Banking and Business, Financial Services and Pensions, Judiciary – Criminal Justice and Corrections, and Utilities Committees.