Improving educator wellbeing presents a complex challenge due to the variety of influences on wellbeing at the individual, relational, and contextual (school and policy) levels. This complexity contributes to the gap between the effectiveness of positive psychology interventions (PPIs) and their real-world success. To bridge this gap, it is essential to understand and adapt to school context when integrating psychological interventions into educational settings. This study addresses this gap through an approach to developing an educator wellbeing program that embraces the idea of understanding and adapting to context. We use a theory of change approach to designing a program, that outlines the context, design rationale, activities, and outcomes of the program. The program is multi-level, targeting influences on educator wellbeing at the individual, relational, and contextual (school) levels. Additionally, it employs a multi-foci strategy, encompassing a range of activities that target different levels and allow for adaptation. We present a case study of program implementation in one school, exploring contextual factors, adapting the program accordingly, and evaluating the degree to which theory of change outcomes were achieved. Program participants experienced improved wellbeing and a relational space characterised by more positive interactions with colleagues. This design and case study contribute to the ongoing discourse on progressing towards context-specific, whole-school approaches to wellbeing.