Master Chief Webb was born and raised in upstate New York. He graduated from Canastota High School in June 1989 and enlisted in the Navy in May 1991. Following completion of basic training at Recruit Training Command, Orland, FL he reported to Naval Technical Training Center Meridian, MS for Personnelman “A” School.
In October 1991, he reported for duty at Personnel Support Detachment Little Creek where he worked in the Transient Personnel section and was advanced to Petty Officer 3rd Class.
In December 1993, Master Chief Webb reported to USS DWIGHT D. EISENHOWER (CVN 69). While aboard, he deployed to Haiti, 6th Fleet and 5th Fleet. He served as Educational Services LPO and was advanced to Petty Officer 2nd Class.
For his next shore assignment, he reported to Personnel Support Detachment Pensacola where he worked as a student records clerk and enlisted classifier. He was advanced to Petty Officer 1st Class and selected for conversion to Cryptologic Technician (Technical).
After completing CTT “A” School, he reported to Naval Security Group Activity San Diego as a Direct Support Operator and Supervisor. He completed RIMPAC 2000 and WESTPAC deployments aboard USS BOXER (LHD 4) and USS BELLEAU WOOD (LHA 3).
In July 2003 he reported to the National Security Agency where he was selected for Chief Petty Officer and served as the Maritime Senior Watch Officer on the National Security Operations Center watchfloor.
Master Chief Webb returned to sea duty in 2006 aboard USS BENFOLD (DDG 65). He completed two deployments as Operations Department LCPO and VBSS Boarding Officer in support of Operation ENDURING FREEDOM and was selected for Senior Chief Petty Officer.
In 2009, he reported to Naval Medical Center San Diego as the Physical Evaluation Board Liaison Officer, was advanced to Master Chief Petty Officer, and selected for the Command Master Chief program.
In 2012, Master Chief Webb reported to the Golden Warriors of VFA 87 as the Command Master Chief. While there, he deployed to 6th Fleet and 5th Fleet with CVW 8 embarked on USS GEORGE H. W. BUSH (CVN 77).
Master Chief Webb is a graduate of CMC/COB school and Senior Enlisted Academy and recipient of the prestigious Peter Tomich Distinguished Leadership Award. Additionally, he holds a Master Degree in Public Administration and Organizational Leadership.
His personal decorations include the Defense Meritorious Service Medal, Navy and Marine Corps Commendation Medal (four awards), Navy and Marine Corps Achievement Medal (six awards), and various unit and campaign awards.