The functionality of academic institutions has, in general, evolved around vision and mission statements, together with some strategic planning commensurate with those statements. Most academic institutions in the Western sphere have well-defined strategic goals, but in the developing world, including Arab countries, these plans have generally been poorly defined. Moreover, even when the strategic planning of these institutions has been well framed, its implementation has generally fallen short, as has the ability to gauge these shortcomings. In the past 10–15 years, academic institutions in the Arab world have started to put together more robust strategic plans accompanied by the executive plans to fulfill their targeted goals. In recent years, academic institutions in the Arab world have come to realize the necessity to move forward with the digital transformation of their academic models. Most of these institutions have automated not only their academic-model delivery systems but to also, to varying extents, the execution of their strategic goals, including ways to measure the degree of achievement of such goals. This has created a method by which the performances of faculty members, the administrative staff and students can be gauged against the requirements embedded in the strategic and executive plans of the participating institutions. During the past decade, the University of Jordan has committed to developing a state-of-the-art strategic plan that reflects the aspirations and ambitions of a rapidly developing academic institution in the Middle East. Recently, portfolios of student, faculty and course goals, with outcomes, were set up to assist with strategic planning. In this chapter, we will review the various processes involved in the execution of the strategic plans of the university and for each process will offer certain levels of insight of the machine learning and AI deployments that have been harnessed in the overall paradigm. This will show pronounced evidence of how the University of Jordan has carried out the execution paradigms that have put the institutional strategic planning into good running order.