He is the State Air Surgeon of the Maryland Air National Guard (MDANG) Joint Force Headquarters, Warfield Air National Guard Base (ANGB), MD. He entered the U.S. Air Force on active duty in August 1989 through enlisted Basic Military Training and soon after completed aircraft maintenance qualification. In 1990, he was assigned to the 526th Tactical Fighter Squadron at Ramstein Air Base (AB), Germany, serving as an F-16C Crew Chief. In 1992 he was reassigned to the 389th Fighter Squadron at Mountain Home AFB, ID. In 1993, he transferred to the MDANG to serve as an A-10A Crew Chief. He graduated from the Academy of Military Science and received his officer commission in 1997. In 1998 he earned his pilot wings upon graduating from Undergraduate Pilot Training at Laughlin AFB, TX, then completed the Introduction to Fighter Fundamental course with the 49th Fighter Training Squadron at Columbus AFB, MS, and then graduated from A-10A Initial Qualification Training with the 357th Fighter Squadron at Davis-Monthan AFB, AZ.

Col. Woolford resumed his service in the MDANG as an A-10A Pilot assigned to the 104th Fighter Squadron. In 2004, he returned to active duty and was awarded his medical degree in 2008 from the Uniformed Services University. He earned his flight surgeon wings in 2009 upon graduating from the Aerospace Medicine Primary course at Brooks AFB while completing his Transitional Internship at Lackland AFB, TX. That same year, he was assigned to the 25th Fighter Squadron at Osan AB, Korea, serving as a Flight Surgeon. In 2010 he was reassigned to the 81st Fighter Squadron at Spangdahlem AB, Germany, where he was awarded the prestigious role of Pilot-Physician. In 2013, he was selected to attend the Residency of Aerospace Medicine at Wright-Patterson AFB, OH, graduating in 2016. He was then selected as a U.S. Air Force Exchange Officer to the United Kingdom, serving as a senior medical officer at the Royal Air Force (RAF) Centre of Aviation Medicine at RAF Henlow and as a Hawk T1 evaluator pilot at Ministry of Defense Boscombe Down. In 2020 he returned to the MDANG, initially serving as the Chief of Aerospace Medicine and the Deputy State Air Surgeon, and then as the 175th Medical Group Commander. Prior to his current position, he was the Commander of the 380th Expeditionary Medical Squadron at Al Dhafra AB, United Arab Emirates. His awards include the Air and Space Achievement and Commendation (with two oak leaf clusters) Medals, the Army Commendation Medal, the Aerial Achievement Medal, the Air Medal with oak leaf cluster, and the Meritorious Service Medal.