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Jason Stillwell has over 20 years of experience in the fields of military operations analysis and aviation. Jason began their career in 1999 as a P-3C Pilot and Mission Commander at VP-26 in the US Navy. After serving in this role for three years, they transitioned to become a Weapons Officer and Tactical Support Center Watch Officer at CPRW-5. In 2005, Jason joined Systems Planning and Analysis, Inc. as a Program Manager and Senior Military Operations Analyst. Jason is currently in this position, utilizing their extensive expertise in military operations to support the company's projects.

Jason Stillwell began their education in 1991 at Machinist Mate (Nuclear) "A" School. Jason then attended Nuclear Power School at the Naval Nuclear Power Training Command (NNPTC) from 1991 to 1992. Following this, from 1992 to 1996, Jason attended the United States Naval Academy, where they graduated with a Bachelor of Science degree in Ocean Engineering. Additionally, Jason also pursued studies in Oceanography at the University of Michigan, although the exact dates of their enrollment are not provided.