Master Chief Harless, a native of New Castle, Virginia, enlisted in the U.S. Navy in 1996 through the Delayed Entry Program. In 1996, he graduated from Craig County High School in New Castle, Virginia followed by Basic Training in Great Lakes, Illinois, and A-school in Pensacola, Florida.
Master Chief Harless completed Active Component sea duty assignments with VPU-2 Barbers Point, Hawaii, VP-46 Whidbey Island, Washington, VPU-2 Kaneohe Bay, Hawaii, VP-45 Jacksonville, Florida, VP-10 Jacksonville, Florida and shore tours with Search and Rescue Brunswick, Maine, and FRCSE Jacksonville, Florida. Master Chief Harless became the Senior Enlisted Leader of Fleet Readiness Center Southeast Detachment Jacksonville in April 2022.
Master Chief Harless is designated Enlisted Aviation Warfare Specialist and has been awarded the Navy and Marine Corps Commendation Medal (5th award), Navy and Marine Corps Achievement Medal (4th award), and various other campaign, command, and personal awards.