The main aim of the paper is to provide evidence that merging the corporate social responsibility (CSR), the leadership, and the social entrepreneurship literatures informs and benefit all these literatures. With this aim, a literature review on the studies investigating how leaders affect organizational CSR, why organizations engage in CSR, and how the environment affects the leader and the organizational CSR approach has been carried out. The outcome is a microfocused, multilevel, and multitheoretical conceptual framework, able to underline the links between the role of the leader, the organizational CSR approach, and the sustainable development of the territory. The conceptual framework has been applied to the GOEL case study, a strategic alliance operating in an unfavorable context. The findings provide evidence of the pivotal role of the leader in defining the organizational CSR approach and that the societal and cultural contexts affect the way in which leader faces the sustainability challenges.