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Jay "Chewy" Frey has extensive work experience spanning over a decade, starting from 2010 when they were a student at the US Army War College. Jay "Chewy" later joined the US security force working as a special assistant to the Supreme Allied Commander/US EUCOM Commander. In 2014, they became the Assistant Chief of Staff for Standardization (AC/S STAN) of the 2d MAW in the USMC. In 2015, they became the Commanding Officer of Expeditionary Warfare Training Group Atlantic. In 2017 they became the Branch Head of Aviation Expeditionary Enablers in HQMC Aviation. The following year, in 2018, they were promoted to the Branch Head of Air Warfare Systems Unmanned Aerial Systems in HQMC. In 2021 they were the Senior Military Fellow for Center for a New American Security (CNAS). In 2022, they became an Independent Consultant. In 2023, they became a Strategic Advisor twice, first at Albers Aerospace and then at ABSI Aerospace & Defense, where they were later promoted to the Vice President, CxISRT.

Jay "Chewy" Frey received a Bachelor of Science degree in Mechanical Engineering from Virginia Military Institute, where they studied from 1988 to 1992. Jay "Chewy" continued their education in 2005 at the U.S. Naval War College, earning a Master of Arts degree in Strategic Studies, which they completed in 2006. Later in their career, they attended the Army War College in 2010 and 2011, where they received a Master of Arts degree in ASAP.