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School system leaders are beginning to recognize their roles in designing and integrating organizational structures that support the wellbeing of administrators, teachers and staff. This paper provides an overview of findings from an exploratory multiple case study in western Canada of how and why school leaders are able to prioritize system-wide wellness and shift organizational cultures. By examining systems-level change through the lens of school community members (n=20) we identified (a) essential components that shape organizational wellbeing and (b) supporting qualities that foster growth for cultures of wellbeing. A conceptual model for cultivating and sustaining wellbeing across systems is offered for school leaders in establishing and integrating effective, systemic and sustainable approaches to wellbeing within their own educative contexts.