In this paper we seek to elaborate on the theoretical underpinnings of the study of women’s representation and the executive. The bulk of research on women's representation has focused on the relationship between the legislative branch and the different aspects of representation. Nevertheless, the literature focusing on the relationship between women's representation and the executive branch has increased considerably in the past years. Using the case of Dilma Rousseff—Brazil’s first woman president—this paper will elaborate on how a woman president can influence symbolic, descriptive, and substantive representation. Drawing on foundational works (such as Hannah Pitkin’s piece) and on contemporary debates about gender and representation, this paper seeks to explore the complexities of defining and measuring representation. Most notably, this work seeks to contribute to the study of representation by examining in detail the conceptualization of women’s issues, women’s interest, and women’s representation in a particular case (Brazil) while connecting these concepts to the role of the presidency in addressing representational concerns. By linking women’s interest groups, legislative politics, and the office of the President in Brazil, this paper hopes to provide some initial ideas of how scholars can measure the impact a woman president has in the representation of women in the political process.