The son of a career naval officer, Montgomery graduated from the University of Pennsylvania in 1985, received bachelor’s and master’s degrees in History and Political Science, and was commissioned through the Naval ROTC program. He subsequently attended Oxford University, where he earned a master’s degree in History and has also completed the Navy’s nuclear power training program.

From 1988 to 1998, Montgomery served in shipboard assignments as division officer, USS Bainbridge (CGN 25), operations officer, USS Leftwich (DD 984), reactor electrical assistant, USS Theodore Roosevelt�@(CVN 71), and executive officer aboard USS Elliot (DD 967).

Selected as a White House fellow in 1998, Montgomery was assigned to the National Security Council (NSC) from 1998 to 2000. While at the NSC, he served as director for Transnational Threats, coordinating national security policy in the areas of counter-terrorism, information security and critical infrastructure protection.

From 2001 to 2009 Montgomery returned to sea. He was the first commanding officer of USS McCampbell (DDG 85) from 2001 to 2003, during which time the ship was delivered to the Navy and completed two counter-narcotics deployments. He subsequently served as the reactor officer on USS Nimitz (CVN 68) for three years. Montgomery then commanded Destroyer Squadron 15 and Task Group 75.4 from 2007 to 2009, leading the destroyers and frigates assigned to U.S. 7th Fleet, and completing multiple deployments with the Kitty Hawk�@and George Washington�@Carrier Strike Groups.

Montgomery served as the head of the Strategy Branch in the Office of the Chief of Naval Operations. His branch was the principal source for the development and implementation of Navy strategic and operational planning documents. Most recently, he served as deputy director, Plans, Policy and Strategy, United States European Command, Stuttgart, Germany. In January 2013, he assumed command of Battle Force 7th Fleet/Task Force Seven Zero/Carrier Strike Group Five permanently embarked on board USS George Washington homeported in Yokosuka, Japan.

His awards include the Defense Superior Service Medal, the Legion of Merit (two awards), and the Meritorious Service Medal (four awards), and other campaign and unit awards.