This chapter explores the process of leading and implementing digital transformations in educational institutions, particularly in the context of online education. It highlights the key challenges, such as faculty resistance, infrastructure demands, and the necessity for proper faculty training. Additionally, it delves into the strategic role leadership plays in fostering a smooth and effective digital transition. The chapter emphasizes the importance of aligning digital transformation with the institution’s objectives, equipping faculty with the necessary skills, and ensuring the ongoing quality of education through robust assessment and evaluation methods. Using case studies and research-backed strategies, the chapter provides practical guidance for leaders navigating the complexities of online education transformation.