This chapter proposes an in-depth study of higher education leaders (HELs) in Saudi Arabia, with a particular focus on the challenges, obstacles and success factors of talent management (TM) in Saudi universities. A mixed methods study design was adopted in which a general literature review was conducted to uncover the skills gap in the higher education sector and its impact on university leadership, taking into account both the external and internal environments. In addition, a survey would be conducted among a wide range of university leaders, including rectors, vice-rectors, deans, vice-deans and department heads, on the existing TM practices in their respective universities. Through this approach, the authors have uncovered how HELs perceive and deal with the skills gap phenomenon, including the barriers and success factors in TM in their universities, with due consideration of the influence of both external market forces and internal institutional dynamics.