On October 15, 2013, about 1900 central daylight time, an Embraer EMB-500, N610AS, was substantially damaged when it departed the runway while landing at Colonel James Jabara Airport (KAAO), Wichita, Kansas. Both of the Airline Transport rated pilots were uninjured. The airplane was registered to and operated by Executive Flight Services, Inc., and doing business as Executive Airshare. The airplane was being operated under the provisions of 14 Code of Federal Regulations Part 91 as a repositioning flight. Visual meteorological conditions prevailed for the flight, which operated on an instrument flight rules flight plan. The flight originated from Charles B. Wheeler Downtown Airport (KMKC), Kansas City, Missouri at 1816. The pilot flying stated he had recently completed training in the Embraer EMB-500, and that the accident flight was his first flight in an actual EMB-500 airplane. The pilot-in-command elected to place the pilot in the left seat for the flight, and allowed him to perform the approach and landing. The pilots discussed braking procedures and techniques during both preflight and while airborne, which included the necessity to apply braking evenly and firmly. The pilot stated the landing was firm, but not a hard landing, and that the first portion of the landing rollout was "fine". The airplane began oscillating left and right a few seconds after applying full braking, and the airplane became uncontrollable and exited the runway. The airplane came to a stop and both pilots exited the airplane. The airplane was equipped with a flight data recorder. The BRAKE FAIL and BRAKE RH CONTROL VALVE FAIL messages were logged 16-17 seconds after the landing transition. The wheel speeds were zero at the time both messages were recorded. The data did not reveal any braking anomalies or maintenance codes while the airplane was in motion.