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Cozy Bailey, Jr. has a diverse work experience spanning over 15 years. Cozy started their career in the US Navy, where they served in multiple roles, including Assistant Ops Officer and Damage Control Assistant. After leaving the Navy, they worked at Naval Sea Systems Command as a Flag Aide/Action Officer. Cozy then joined Lockheed Martin, where they led the international business development efforts for the surface ship product line. Following their time at Lockheed Martin, Bailey worked as a Consultant at Metropolitan Eye Associates and Honeywell Technology Solutions, Inc., where they led various operations, business development, and capture management initiatives. Cozy also served as the Director of Field Operations at Friends for Andrea Bailey, where they successfully led a political campaign. Bailey's experience also includes roles at Textron Systems - Marine & Land Systems, where they held the positions of International Business Development Manager and Director - Colombia Operations. Most recently, they have been working at Longevity Consulting as the Director of Strategy, Business Development, and Operations, leading growth strategy and business development transformation efforts for federal agencies. Throughout their career, Bailey has demonstrated expertise in strategy development, operations efficiency, pricing, and advertising.

Cozy Bailey, Jr. completed their education with a focus on business and political science. In 1993, they attended the North Carolina School of Science and Mathematics where they completed their high school education. From 1995 to 2000, Cozy Bailey, Jr. pursued a Bachelor of Science degree in Political Science and Government at the United States Naval Academy. In 2012, they furthered their education at the University of Virginia Darden School of Business, where they obtained a Global Executive MBA degree.