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Jason Strickler has extensive work experience in various industries and roles. Jason started their career as an intern at the U.S. Embassy to the Vatican in 1994. Following that, they served in the United States Air Force from 1999 to 2014, where they held positions as an officer, senior director of operations, and pilot.

After leaving the military, Strickler worked as the director of client services and product development at a private financial services company from 2014 to 2016. Jason then became a consultant in organizational leadership and veteran transition, providing their expertise from July 2016 to September 2022.

In 2018, Strickler founded the organization Extraordinarily Ordinary Veteran, which they led until 2023. From 2017 to 2023, they also operated as the lead founder and president of the Fort Worth Veteran Professionals, a Texas nonprofit focused on networking, professional development, and community service.

Strickler further expanded their experience in logistics and operations as an operations manager at Amazon from September 2020 to December 2021. Currently, they work as the director of operations and logistics at Aerolane, starting in March 2022.

Jason Strickler has a diverse education history. Jason obtained a Bachelor of Science (BS) degree in Political Science and Government from the United States Air Force Academy. Jason then pursued further education and received a Master of Arts (MA) degree in Military Operational Arts and Sciences from USAF Air Command and Staff College. Additionally, they attended St Stephen's School in Rome, Italy, where they obtained their High School Diploma with a focus on International Baccalaureate. Furthermore, they completed their education with a Master of Business Administration (MBA) degree from the M.J. Neeley School of Business at Texas Christian University.

In addition to their academic achievements, Jason Strickler has obtained various certifications. Jason holds a Basic Military Parachutist certification from the US Army, and they have acquired multiple certifications related to their roles in the United States Air Force, including C-130 Pilot, Aircraft Commander, Instructor, Evaluator, as well as KC-135 Pilot, Aircraft Commander, and Instructor.