Higher education remains embroiled in transition driven by cost of attendance, technological advances, globalization, hyper-competition, and stakeholder expectations. Concurrently, advances in online education have prompted increased integration within the educational enterprise. Not only are modern institutions faced with the necessity to respond to the changing educational environment, they must establish capabilities to sustain online education into the future. This paper examines the viable system model (VSM) as a mechanism to deal with this complexity and offers a framework through which leadership and management in online education can increase understanding of organizational sustainability and systemic management.