Rear Admiral Ailes was a career surface warfare officer and a member of the defense acquisition community. He was the first commanding officer of the USS Chafee (DDG-90) and commanded the Naval Surface Warfare Center, Port Hueneme Division. He was also the naval integrated fire control project officer and surface ship combat system manager in the Program Executive Office for Integrated Warfare Systems; major program manager, Mission Modules, in the Program Office for Littoral Combat Ships; and chief engineer and deputy commander for fleet readiness at the Space and Naval Warfare Systems Command.