Research on corporate political activity has considered a number of antecedents to a firm’s engagement in politics. The majority of this research has focused on either industry or firm-level motivations that lead to corporate political activity, leaving the role of the firm’s leader noticeably absent in such scholarship. This article combines ideas from Upper Echelons Theory with research in corporate political activity to bridge this important gap. More specifically, this research utilizes CEO demographic characteristics to determine (a) whether a firm will invest in political activity and (b) how these characteristics influence the particular approach to political activity the firm undertakes. Considering 27 years of data from large U.S. firms, we find that a CEO’s age, tenure, functional, and educational backgrounds influence whether and how the firm invests in political activity.