Faced with the massive challenge of personalising learning for a digital generation, educators need to change. Collaboration and collaborative leadership, having been widely researched and implemented, are now considered to be strategic components of systemic transformation. Many jurisdictions have trialled or instituted collaborative or cluster-based projects to address the collaborative learning and leadership challenges associated with transformation through e-learning. New Zealand’s emergent Virtual Learning Network and e-learning clusters have developed new system leadership from grass-roots rural schools with the Ministry of Education’s strategic support. Can these innovative collaborative projects continue to improve and sustainably contribute to educational transformation in NZ? This small-scale qualitative investigation focussed on semi-structured interviews to gather data from five experienced rural cluster Lead Principals who have successfully lead some of the stronger rural Virtual Learning Network e-learning clusters across rural New Zealand. The key research question which guided the interview questions and analysis was: What are the most appropriate and effective models for managing and leading collaborative relationships and shared long-term projects for clusters of secondary schools? The aim was to discover the conceptions and use of collaborative processes, structures and leadership which theoretical and empirical research suggest are critical components of system-wide reform. Research findings reveal a high degree of congruence between theory and the practice of these five Lead Principals. Their understanding and practice of shared, distributive and collaborative leadership, with a clear commitment to building leadership capacity, was based more upon their personal style supported by some knowledge of the international literature, rather than formal policies. However, while these maturing clusters have outlasted many others, they continue to face challenges of viability, effectiveness, and sustainability, in spite of the Ministry of Education’s support for critical background infrastructure. The data shows that while there are strong collaborative support strategies in and for these clusters, two key areas could be addressed more effectively. This study suggests that collaborative transparency and accountability needs strengthening in a drive for consistent quality and effectiveness. Also, while new structural cluster models may be emerging in the search for sustainability, the well-established cost of managing collaborations has not yet been accepted by the MoE, leaving 100% of the burden of management costs on the mostly small rural schools. It is therefore recommended that the MoE find a way around the current school-based funding model to at least partially fund regional management of these transformative collaborations, perhaps within the government’s current drive to build performance management and accountability. New Zealand’s systemic transformation and its current leadership within the e-learning revolution may depend on it.