| Military Highlights | - Role: F-16 Fighter Pilot, Command Pilot (>2,800 hours, 150+ combat) Period: 1990s-2000s
- Role: Chief of Weapons and Tactics, 121st Fighter Squadron, patrolled DC post-9/11 Period: 1998-2002
- Role: Chief of Group Weapons and Tactics, 332nd Air Expeditionary Wing, Kuwait Period: 2001-2002
- Role: National Guard Period: 2009-2016
- Role: Assistant to Vice Commander US Special Operations Command & Assistant Commanding General Joint Special Operations Command Period: 2016-2018
- Role: Deputy Commanding General, Special Operations Command Central & Operation Inherent Resolve Period: 2018-2019
- Role: Associate Director for Military Affairs, CIA Period: 2021-2024
- Role: F-16 Instructor Pilot, 138th Fighter Squadron, Syracuse, NY Period: 1994-1998
- Role: F-16 Instructor Pilot and Chief of Weapons, 121st Fighter Squadron, Andrews Air Force Base Period: 1998-1999
- Role: Chief of Weapons and Tactics, 121st Fighter Squadron, patrolled DC post-9/11 Period: 2001-2002
- Role: Counter-SCUD Project Officer, U.S. Special Operations Period: 2002-2003
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| Business Ventures | - Company: The Caine Group (Founder) Focus: National security investment/consulting Year: 2010
- Company: RISE Air (Co-founder, COO) Acquired by: Surf Air Year: 2017
- Advisor: Voyager (space tech), Thrive Capital Current: Partner at Ribbit Capital, Shield Capital (joined 2025)
- Company: The Caine Group (Founder) Focus: National security investment and consulting Year: 2010
- Advisor/Partner: Voyager (space technology), Thrive Capital, Ribbit Capital, Shield Capital
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