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Thomas Bailey has a diverse work experience in various roles and companies. Thomas began their career in the US Air Force, serving in multiple positions such as Director of Standardization and Evaluations and Deputy Director of Wing Plans & Programs. Thomas then worked as a Program Manager for Distance Learning & International Training Programs at the Inter-American Defense College. Bailey also served as a Financial Advisor at Merrill Lynch and as an Operations Manager at Engility Corporation. More recently, they have worked at Bowhead, Highground & Camber Corporations/US Southern Command as a Senior Readiness Analyst, where they trained and advised staff on Defense Readiness Reporting System (DRRS) and assisted with the preparation of reports. Currently, Bailey is serving as the Chief of Readiness at the United States Southern Command, where they oversee the analysis of SOUTHCOM's ability to execute its portion of the National Military Strategy and coordinates reporting across various headquarters, components, joint task forces, and security cooperation organizations.

Thomas Bailey has a strong educational background, with degrees spanning multiple disciplines. Thomas earned a Bachelor of Science (B.S.) in Civil Engineering from Villanova University, completing their studies from 1983 to 1987. Later, they pursued a Master of Science (M.S.) in International Relations from Troy University, attending from 1995 to 1998. Thomas then furthered their education by obtaining a Master of Business Administration (MBA) degree with a focus on Finance & Investing from The Johns Hopkins University - Carey Business School, where they studied from 2006 to 2008.

In addition to their formal degrees, Thomas Bailey has attained two certifications, namely the Chartered Retirement Planning Counselor (CRPC) and the Contingency Wartime Planner. Unfortunately, no further information regarding the institutions or the specific years these certifications were obtained is provided.