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Command Master Chief Rollert entered the Navy in June 1997 and completed Basic Training at Recruit Training Command Great Lakes, Ill. After completing Basic Enlisted Submarine School (BESS) and Electronics Technician “A” School in Groton, CT, he transferred to USS Annapolis (SSN 760), homeported in Groton. He was a member of the Communication Division, where he earned his Enlisted Submarine Warfare pin and completed one Mediterranean deployment.
From February 2001 until April 2002, he was assigned to SUBASE New London Broadcast Control Terminal and was advanced to Second Class Petty Officer. From April 2002 until August 2003, he completed various IT/Network and Communications schools at Naval Submarine School in Groton, CT. In August 2003, he reported to USS Miami (SSN 755), homeported in Groton, CT., and was assigned to Communications Division, where he was advanced to First Class Petty Officer and completed a Mediterranean deployment and a Northern Atlantic Deployment. In December 2005, he transferred to Center for Information Dominance Det Groton CT as the lead EKMS Instructor where he was advanced to Chief Petty Officer.
In January 2009, he transferred to USS Pasadena (SSN 752), homeported in Pearl Harbor, HI, as the Communication Division Leading Chief Petty Officer. While onboard, he completed two Western Pacific deployments, a transit of the Panama Canal for a homeport shift to Kittery ME for an extended overhaul and advanced to Senior Chief Petty Officer. After completing Senior Enlisted Academy (Class 170), he transferred in December 2012 to Submarine Squadron One in Pearl Harbor, HI., and served as the Squadron Communications Assistant. During this time, he completed qualifications for Chief of the Boat.
In September 2014, he reported aboard USS Jacksonville (SSN 699), homeported in Pearl Harbor, HI., as Chief of the Boat. While onboard, he advanced to Master Chief Petty Officer and completed an extended Western Pacific Deployment and a 7 1ò2 month Persian Gulf Deployment that culminated with USS Jacksonville being awarded the 2017 Submarine Squadron One Battle “E” award. In November 2017, he transferred to Submarine Squadron Eleven and was sent TAD to USS Hampton (SSN 767) as Chief of the Boat while in overhaul in Kittery ME. He transferred in May 2018 to Submarine Learning Center Det. San Diego, Calif., as the Senior Enlisted Leader. He was selected into the Command Master Chief program and reported to Navy Talent Acquisition Group (NTAG) Heartland in October 2020.
Master Chief Rollert is entitled to wear the Navy Meritorious Service Medal (two awards), Navy and Marine Corps Commendation Medal (two awards), Navy and Marine Corps Achievement Medal (three awards), Navy Unit Commendation Ribbon, Meritorious Unit Commendation Ribbon, Navy Battle ‘E’ Ribbon, Navy Good Conduct Medal (seven awards), Navy Expeditionary Medal, National Defense Service Medal, Global War on Terrorism Expeditionary Service Medal, Global War on Terrorism Service Medal, Arctic Sea Service Ribbon, and the Sea Service Deployment Ribbon (7 awards).