ESIMS is a training management system tailored to answer the unique needs of the Air Force (AF) Security Cooperation (SC) Enterprise and broader SC Enterprise. ESIMS' mobile app provides AF SC training providers (Air Advisors, Combat Air Advisors, Schoolhouses, etc.) with a tailored training management system makes managing & executing their training engagements with International Military Students (IMS) easier and more effective. The very intentional side-effect of ESIMS' mobile app usage is increased quantity and quality of IMS data and data products (After Action Reports, Lessons Learned, etc.) that are made available to the SC Enterprise through ESIMS' Government cloud backend that enables data-driven decision support, IMS alumni engagement, action recommendations, and business intelligence (BI) for AF SC and broader SC Enterprise stakeholders at all levels. ESIMS's RAPID Phase II will enable the equivalent of an "automated staff officer" through the implementation of machine learning and cognitive services for the AF SC Enterprise and broader SC Enterprise. These communities will experience these features in the form of key insight reports designed to promote further data-driven decision support from ESIMS' SC and IMS data.