Referred to as change agents, innovators, practical dreamers, and pioneers of our era, the literature on social entrepreneurs exhibits high hopes for the future of social enterprise in international development. Yet, the field has come to a crossroads in its history as many remain unsure of just how social enterprise differs from NGOs on the one hand, and standard commercial enterprises on the other. This article examines the relatively new roots of social entrepreneurship in the context of global development paradigms, looking at the pros and cons of a field which remains controversial from the perspective of both the private and the public sector. Using the model of the prominent social enterprise KickStart International, we illustrate how KickStart’s social enterprise model corresponds with current trends in the world of development internationally, with its particular focus on sub-Saharan Africa. Finally, we examine how recent evaluation research has shed light on KickStart and the contributions of social enterprise, as well as how evaluation research can inform social enterprise’s contributions to international development.