Col. Randy P. Oakland is the Director of Operations and Communications at Headquarters Air Education and Training Command, Joint Base San Antonio-Randolph, Texas. He is responsible for the world's largest training organization, providing initial skills, undergraduate flying, post graduate combat crew and supplemental training for over 300,000 Air Force, joint and international personnel at 65 Air Force and Department of Defense locations. Col. Oakland provides strategic vision, policy, guidance, and advocacy to build, operate, secure, defend and extend the Air Force portion of the Department of Defense global network. Additionally, he executes force development policy to ensure the training, education and experiences of Total Force Airmen achieve desired competencies to meet U.S. Air Force needs, providing the right Airman in the right place at the right time.

Col. Oakland was commissioned as a graduate of the United States Air Force Academy and earned his Doctor of Philosophy in Military Strategy from Air University. He has served in numerous positions at the squadron, wing, air operations center, numbered air force, and sub-unified command levels. Col. Oakland is a command pilot with more than 2,600 hours in the F-15C/D, T-37, and T-38. His operational experiences include operations Northern Watch, Iraqi Freedom, and New Dawn. Prior to his current position, the colonel was the Director of Operations for 19th Air Force, JB San Antonio- Randolph, Texas.


1996 Bachelor of Science, Behavioral Science, U.S. Air Force Academy, Colo. 2002 Squadron Officer School, Maxwell Air Force Base, Ala.

2004 Master of Business Administration, Trident University International, Calif.

2006 Air Command and Staff College, Maxwell AFB, Ala., by correspondence

2009 U.S. Army Command and General Staff College, Fort Leavenworth, Kan.

2010 Master of Airpower Arts and Science, School of Advanced Air and Space Studies, Maxwell AFB, Ala. 2012 Air War College, Maxwell AFB, Ala., by correspondence

2015 Joint and Combined Warfighting School, Joint Forces Staff College, Norfolk, Va. 2016 Lorenz Fellowship, Air University, Maxwell AFB, Ala.

2017 Doctor of Philosophy, Military Strategy, Air University, Maxwell AFB, Ala.

2019 Leading Strategically, Center for Creative Leadership, Colorado Springs, Colo.

2019 Enterprise Perspective Seminar, Alan L. Freed Associates, Washington, D.C.

2022 Combined Force Air Component Commander Course, Air University, Maxwell AFB, Ala.


  1. October 1996––December 1997, Student, Euro-NATO Joint Jet Pilot Training, Sheppard Air Force Base, Texas
  2. May 1998––October 1998, Student, F-15C Fighter Training Unit, Tyndall AFB, Fla.  
  3. November 1998––January 2002, Electronic Combat Officer, 71st Fighter Squadron, Langley AFB, Va.
  4. February 2002––November 2003, Graduate Student Flight Commander, 80th Operations Support Squadron, Sheppard AFB, Texas
  5. November 2003––May 2005, Flight Commander, 88th Flying Training Squadron, Sheppard AFB, Texas
  6. August 2005––May 2007, Squadron Executive Officer, Flight Commander, and Assistant Director of Operations, 12th Fighter Squadron, Elmendorf AFB, Alaska
  1. May 2007––June 2008, Wing Executive Officer, 3rd Wing, Elmendorf AFB, Alaska
  2. June 2008––June 2009, Student, Command and General Staff College, Fort Leavenworth, Kan.
  3. June 2009––June 2010, Student, School of Advanced Air and Space Studies, Maxwell AFB, Ala
  4. July 2010––July 2011, Deputy Division Chief, J5 Strategy, Headquarters United States Forces-Iraq
  5. September 2011––November 2011, Student, T-38C Pilot Instructor Training, 560th FTS, Randolph AFB, Texas
  6. March 2012––May 2013, Director of Operations, 87th FTS, Laughlin AFB, Texas
  7. May 2013––April 2015, Commander, 87th Flying Training Squadron, Laughlin AFB, Texas
  8. July 2015––July 2016, Student, Lorenz Fellow, Washington, D.C
  9. August 2016––June 2017, Strategy Division Chief, 603rd Air Operations Center, Ramstein Air Base, Germany
  10. June 2017––June 2018, Vice Commander, 12th Flying Training Wing, Joint Base San Antonio—Randolph AFB, Texas
  11. July 2019––July 2020, Commander, 39th Air Base Wing, Incirlik Air Base, Turkey
  12. August 2020––May 2022, Director of Operations, 19th Air Force, JB San Antonio—Randolph, Texas
  13. May 2022––present, Director of Operations and Communications, Headquarters Air Education and Training Command, JB San Antonio-Randolph, Texas


1. July 2010––July 2011, Deputy Division Chief, J5 Strategy, Headquarters United States Forces-Iraq, as a lieutenant colonel



Rating: command pilot

Flight hours: more than 2,600

Aircraft flown: F-15C/D, T-37 and T-38



Legion of Merit with oak leaf cluster

Defense Meritorious Service Medal

Meritorious Service Medal with three oak leaf clusters Air Medal

Air Force Commendation Medal Joint Service Achievement Medal Air Force Achievement Medal

Combat Readiness Medal with two oak leaf clusters



Second Lieutenant May 29, 1996

First Lieutenant May 29, 1998

Captain May 29, 2000

Major April 1, 2006

Lieutenant Colonel December 1, 2010

Colonel March 1, 2017


(Current as of May 2022)