Montgomery is set to make his third U.S. Open start. Montgomery's biggest professional victory to date is the 2019 Long Beach Open. He was the runner-up in the 2020 LECOM Suncoast Classic on the Korn Ferry Tour, losing a three-way playoff with eventual winner Hayden Buckley and Dawson Armstrong. He played his collegiate golf at the University of Nevada-Las Vegas. In 2018, he won a mini-tour event in Utah, the Sand Hollow Leavitt Group Open.