CW4 (Ret.) Terry A. O’Brien is a seasoned aviation entrepreneur with over 28 years of experience across a broad range of professional roles in aviation and operations support. He served for over 18 years as an active-duty Pilot and 3 years as a flight crew chief and maintainer on the UH-60 A/L/M Blackhawk. His aviation background includes planning and executing aviation operations, as well as training and advising across multiple echelons, from the troop level to the Office of the Secretary of Defense & the Executive Branch of Government. He specialized in maintenance, tactical operations, personnel recovery, Continuity of Operations (COOP) & Government (COG), with nearly a decade of service in Medical Evacuation (MEDEVAC) operations across multiple combat and operational deployments.  He is formally trained in Theater-level Combat Medical Evacuation Planning, Global Personnel Recovery Planning & Operations, Disaster Planning & Response, and brings extensive real-world experience integrating aviation assets into complex plans and austere environments.

 

Terry spent many years dual-tracked as a Maintenance Test Pilot (MTP) & Tactical Operations Officer (TACOPS), serving in leadership roles including Maintenance Manager, Aviation Production Control Officer, Aviation Technical Supply Officer, Tactical Operations Liaison Officer, and Personnel Recovery Officer. Outside his normal operational-level roles and responsibilities, he was selected to fill positions that directly support and influence Theater- and National-level plans, operations, and capabilities. He thrived in these untraditional positions because of his uncanny ability to “hover above” complex issues, view them from unorthodox angles, formulate solutions, step back, and tackle them with testable plans that have shaped several strategic programs for the National Capitol Region, the Army, and the Joint Force.

 

His senior leadership assignments also include serving as the TAAB’s National Capital Region Aviation and Integrated Ground Mobility COOP and COG Director, where he was responsible for 24/7 operational evacuation readiness, continuity planning, live exercise, and crisis response in high-visibility, mission-critical environments, supporting a combination of the most senior levels of government and several of its agencies. Terry was assigned to US Army First (I) Corps HQ as Director of Personnel Recover (PR) responsible for managing more than 40,000 service members and civilians around the world under I Corps Command, and two additional positions in the I Corps Aviation Maintenance Manager and Aviation Mission Survivability Officer playing a key role in the development and implementation of the aviation element to the Army Multi Domain Task Force (MDTF) pilot program from inception through its designation as an Army Program of Record, now actively supporting the Joint Force and our Multi-National partners in deterring, shutting down, protecting us from our enemies, and enhancing the survivability and effectiveness of our warfighters.

 

At Cashimee, Terry leads the Survivability Solutions portfolio, integrating aviation survivability, MEDEVAC and CASEVAC planning, disaster response operations, and operational risk mitigation into the company’s Prevent–Protect–Prepare framework. He works closely with executive leadership, operations, logistics, EMSO/UAS teams, and disaster-health security leadership to ensure Cashimee clients and personnel benefit from best-in-class survivability planning and execution.

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Terry is also actively engaged in supporting and volunteering with Humanity Aid and Disaster Response (HADR) missionary operations, applying his aviation, logistics, and leadership expertise to humanitarian relief and disaster recovery worldwide. He holds a Bachelor of Science in Business Management and is currently pursuing a Master of Arts in Christian Ministry, integrating strategic leadership with service-driven mission focus.

 

Recognized for his technical expertise, calm leadership under pressure, and mission-first mindset, CW3 (Ret.) Terry O’Brien brings a lifetime of operational credibility to Cashimee—ensuring survivability is not an afterthought, but a core operational principle.

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 Silent. Strategic. Secure.