This article draws from a larger study of the postcolonial experiences of an Afro-Caribbean religious group called the Spiritual Baptists (of Barbados). It examines the question of gender agency as women and men contest the need to transform traditional and ecclesiastical organizational structures that served them well in their formative years. While being confronted with the reality that some of the structures that have been internalized are oppressive, gender agency emerges as a cultural identity that is navigated, contested, and manifested through younger members at the intra-interorganizational levels of experience. Group-as-a-whole theory provided an ontological understanding of how this agency is communicated within the Spiritual Baptist Church both at conscious and unconscious levels of interaction. As a cultural insider, the author was able to draw on the nuances of the organizational culture to make sense of the complex interrelatedness of subgrouping, religious identity, privilege, leadership-followership dynamics, and personal desire which got encoded in the discourse for greater authorization within the seemingly discrete gendered roles. Further, the author drew on a body of research on masculinity within a postcolonial context of the wider society from which this organization breathes its existence. To retain the authenticity of the voice of these agents, unstructured focus groups provided the mechanism of data gathering of the phenomenological experiences of the group-as-a-whole.