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Jack Sile has a diverse work experience that spans multiple organizations. Jack most recently served as the Vice President at JCTM starting in April 2023. Prior to that, from August 2021 to April 2023, they worked as a Senior Advisor/Intelligence Officer at the Office of the Director of National Intelligence. Jack also held positions at The Joint Staff, where they worked as the Chief of the Regional Intelligence Branch from August 2018 to August 2021, and as a Senior Intelligence Analyst from August 2017 to August 2020. Before that, from August 2015 to August 2018, they served as the II Marine Expeditionary Force Deputy G-2 in the United States Marine Corps.

Jack Sile obtained their Bachelor of Science degree in Architecture from The University of Texas at San Antonio in 1996.