Enlisting in the Navy as a Personnelman in 1991, his first duty station was Personnel Support Detachment South Weymouth. While there, he was selected for the Enlisted Commissioning Program. After commissioning and completing Surface Warfare Officer School in 1999, he reported to USS MCINERNEY (FFG-8), serving as Electrical Officer, Main Propulsion Assistant, and Combat Information Center Officer. CAPT Webber next reported to Destroyer Squadron 24 as the Command, Control, Communications, and Computers Officer, Strike Officer, and Training Officer. Upon completion of this assignment, he reported to Recruit Training Command Great Lakes as the Administrative Officer and Group Commander from 2003 to 2006 where he led 38 Recruit Division Commanders and 1,270 Recruits.
In July of 2006, CAPT Webber reported to Naval Service Training Command Great Lakes as the Current Operations Action Officer. During his next tour, CAPT Webber served as the Training Officer aboard USS RONALD REAGAN (CVN-76) from June 2009 to July 2011 serving as both Officer of the Deck (Underway) and Command Duty Officer. He served on the staff of the Assistant Secretary of the Navy (Manpower and Reserve Affairs) from 2011 to 2014. CAPT Webber led Navy Recruiting District Minneapolis as both the Executive Officer and Commanding Officer from 2014 to 2017. He oversaw all Navy enlisted and officer recruiting operations in an area encompassing 393,000 square miles across seven states.
In 2017, CAPT Webber assumed duty as the Director of Manpower and Personnel (J1) at Special Operations Command Central in MacDill AFB, FL. He was responsible for the manning of a Joint Special Operations HQ in support of 8 Special Operations Task Forces and 8,000 personnel.
During his most recent assignment, CAPT Webber served as the Military Human Resources Division Chief at U.S. Africa Command in Stuttgart, Germany. He presently serves as the Deputy Commander of Navy Recruiting Region West in Millington, TN.