The Chief Online Learning Officers’ Guidebook explores the essential competencies required of Chief Online Learning Officers (COLOs) using insights from real-world leadership and expert perspectives from higher education. Digital and online learning have become strategic priorities for higher education institutions working toward enrollment growth, learner engagement, revenue generation, brand diversification, and enhanced student flexibility following the initial COVID-19 lockdown. This book’s unique framework substantiates and demonstrates key competencies that define the COLO role and enable advancements in the practice of online and digital higher education. Featuring over 50 contributions from COLOs, Chief Information Officers (CIOs), university presidents, and other higher education leaders, this UPCEA-endorsed guide offers practical strategies and comprehensive guidance for both current and aspiring COLOs.