In the issue-selling literature, little attention has been paid to the struggles of those managers who try to sell social issues to potential issue buyers who are not particularly sensitive to the normative elements of these social issues. In this study, we examine the case of Corporate Social Responsibility (CSR) and concomitant dynamics of selling social issues and address two interrelated questions. First, how do the sellers of social issues perceive themselves and their organizational roles, and how does this motivate them to engage in selling social issues in the first place? Second, how do these perceptions influence the strategies that issue sellers use to win over skeptics? To answer these questions, we focus on the relationships that issue sellers build with buyers and on the role of this form of engagement in overcoming resistance to social issues. Our findings shed new light on the motivation, aspirations, and strategies of issue sellers and suggest that a relational approach can provide important insights into understanding selling and buying social issues within organizational contexts. Furthermore, our findings pave the way for future research on selling social issues as a relational endeavor.