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This paper presents a case study of the Barbados Initiative, a transnational partnership between Teachers College, Columbia University and Erdiston Teachers' Training College. Rooted in decolonial pedagogy and Caribbean epistemologies, the initiative challenges colonial legacies in education through certificate programs that prepare teachers and school leaders to lead with cultural responsiveness, critical consciousness, and community care. This presentation outlines how the curriculum centers localized leadership frameworks and transformative teaching, and how the initiative exemplifies a model of South-North collaboration that advances educational equity. We present data from coursework, reflections, and educator practice to highlight implications for postcolonial education reform in the Caribbean.