This book highlights the exigency of student success and how higher education institutions are addressing this call. On the heels of the COVID-19 global pandemic, institutions have been challenged further to manage student satisfaction issues, enrollment and financial insecurities, equity, inclusion and access. As starting point to these ongoing priorities, this book aims to raise awareness, questions and suggestions based on examples of courageous leadership that support retention and completion agendas but more so visionary and actionable approaches to ensure student success. The book addresses the various tensions among education stakeholders, the impressions of change, the expanded realities of competition, the casualties of silos, the value of examining and understanding data in advancing options, and the merits of collaboration, and opportunity thinking. Cases and interviews with thought leaders who candidly share experiences and realizations about ensuring student success provide insight about what else can be done to move the needle forward.