Chief Master Sergeant Raymond Kessner
Director, Veteran Success & Reintegration Office • Executive Committee
Chief Master Sergeant Raymond Kessner serves as Director, Veteran Success & Reintegration Office for Second Mission Shield and as a member of the Executive Committee.
A senior enlisted Air Force leader, Ray brings extensive experience in military leadership, operational responsibility, and service member development to the SMS mission.
His career includes service across Air Combat Command and Air Force Special Operations Command, with repeated deployments in direct support of combat operations alongside special operations forces. He served as an AC-130 Evaluator Sensor Operator and senior leader responsible for mission execution, readiness, accountability, and force development.
At Second Mission Shield, Ray helps lead veteran success and reintegration efforts through VSRO. His background supports SMS’s work in veteran connection, transition support, resource navigation, and long-term reintegration, grounding the program in proven leadership and the realities of life during and after extended military service.