Commander Webb enlisted in the Navy in 1985, as an Aviation Anti-Submarine Warfare Operator and flew with Patrol Squadron NINE THREE the "EXECUTIONERS."  While serving with the Executioners he made numerous deployments to Europe and the Caribbean. In 1992, CDR Webb reported to Aviation Officer Candidate School at Naval Air Station (NAS) Pensacola Florida receiving a commission in January 1993.  He earned his Wings in 1994 and was assigned to Tactical Electronic Attack Squadron ONE THREE SIX at Naval Air Station Atsugi, Japan.  From 1996 to 1999, while assigned to VAQ-136 "GAUNTLETS" deploying aboard CV 62 the USS Independence he completed three major and numerous minor deployments.  Including operations off the coast of Taiwan in 1996 where the USS Independenceled a two carrier Battle Group (BG) providing a stabilizing presence during the Third Taiwan Straight Crisis.  In 1998, he participated in an emergency deployment of the USS Independence Battle Group to the Arabian Gulf, flying Operation Southern Watch missions.  In late 1998, VAQ-136 shifted from CV-62 to CV-63 the USS KITTY HAWK and participated in the "Hawk’s” first deployment as the new permanently forward deployed carrier.  

    From 1999 to 2001 CDR Webb was assigned to Training Air Wing SIX (TRAWING 6) as an instructor.  While assigned to TRAWING SIX he served as the Liaison Officer to the Chief of Naval Air Training, the Advanced Jet Attack Course Curriculum Coordinator and the Assistant Operations Officer.  In January of 2001 to June 2003, he served as the Strike Operations Officer for the Commander of the Commander Carrier Group SIX (COMCARGRU SIX).  While assigned to COMCARGRU SIX he flew with Electronic Attack Squadron ONE FOUR ZERO the "Patriots.” After 11 September 2001, CDR Webb deployed with the USS John F. Kennedy (CV 67) BG to the 5^th Fleet Area of Operations (AOR) participating in Operation Enduring Freedom.  

    In 2003, he was assigned to Electronic Attack Squadron ONE THREE ZERO the "ZAPPERS" at NAS Whidbey Island, Washington.  In 2004 CDR Webb deployed to the Arabian Gulf, aboard the USS Harry S. Truman (CVN 75), participating in Operation Iraqi Freedom flying missions during the historic Iraqi election of 2005.  In 2006, the Zappers were deployed to Marine Corps Air Station, Iwakuni, Japan. 

    In March of 2007, CDR Webb was assigned to United States Strategic Command (USSTRATCOM) in Omaha, NE.  While assigned to USSTRATCOM he served as the Aide-de-Camp to the Commander, General Chilton, USAF until April 2009.  In June 2010, CDR Webb received orders to NATO Air Training Command-Afghanistan, Kabul, Afghanistan.  Upon arriving in Kabul he was reassigned to the 738^th Air Expeditionary Advisory Group (738^th AEAG) as the Deputy Group Commander.

   In July 2011, CDR Webb was assigned to Joint Forces Component Command-Global Strike (JFCC GS) and became the Deputy Director of the Command, Control, Communications, and Computer Systems Directorate.  In 2017, JFCC GS became part of USSTRACOM J5 and CDR Webb was selected to serve as the J5 Chief of Staff.  In February 2021 CDR Webb retired from the United States Navy.

    Commander Webb has a Masters Degree from Auburn University in International Relations, and a Masters in Military Operational Art and Science from the Air University.  His military decorations include the Defense Meritorious Service Medal, with two oak leaf clusters; Air Medal, two Strike Flight awards; Navy Commendation Medal, with two gold stars; Naval Achievement Medal, with one gold star, among various other personal and campaign awards.