This book examines the social entrepreneurship strategies of nonprofit organizations (NPOs), with a focus on the Caribbean social sector. In addressing the conceptual ambiguities from an academic and experiential perspective, it aims to provide a much-needed reflection on social entrepreneurship (SE), including in developing contexts. Through a comparative analysis of the experiences of NPOs from the Caribbean, the authors demonstrate the applicability of SE for NPO sustainability and as an opportunity for social sector performance improvement. Blending both quantitative and qualitative methodologies, this work is a useful base for researchers wanting to advance the mission of theory and methodological development toward maturing the field of social entrepreneurship.