In this chapter, we explore various leadership roles within health professions education, such as Deans, Chairs, Vice Chairs for Education, and Associate/Assistant Deans. We outline the pathways to these roles, emphasizing the importance of developing essential leadership skills, seeking mentorship and coaching, and creating an academic portfolio. The chapter also highlights the need to align leadership opportunities with personal and professional goals, providing practical advice on navigating career trajectories and addressing potential barriers. Through detailed examples and strategies, we aim to guide individuals in building a successful and fulfilling leadership career in health professions education.