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Drew Fitzsimmons has a diverse work experience, starting with their most recent position as a Customer Success Manager at Everactive. Prior to that, Drew worked as a Case Officer at the Central Intelligence Agency from March 2020 to March 2023. Before joining the CIA, Drew was an Executive Assistant at the Office of the Under Secretary of Defense for Intelligence & Security from July 2019 to February 2020. Drew also served as a Military Intelligence Officer in the US Army from May 2014 to May 2019.

Drew Fitzsimmons completed their Bachelor of Science degree with honors in Law at the United States Military Academy at West Point from 2010 to 2014. In addition, they obtained the Advanced Open Water Diver certification from PADI in October 2018.