Over an 18-month period four New Zealand educational institutions--a university, a private tertiary enterprise, a wananga, and an institute of technology/polytechnic--have engaged in a process of change influenced by technology. Their e-learning capability was benchmarked using the E-Learning Maturity Model, and this information was used to stimulate change activities. The resulting case studies, discussed in this paper, illustrate the issues that face tertiary organisations and leaders engaging with the opportunities and challenges of e-learning. Five factors have been identified as significant influences on the ability of organisations to change in response to technology in the current political and educational landscape of the New Zealand tertiary sector.