In order to explain the sparse representation of women in leadership positions across U.S. society, I propose a theoretical model delineating the processes underlying executive advancement. I argue that organizational gatekeepers making hiring and promotion decisions are fundamentally engaged in a risk assessment process in which they consider both risks associated with the characteristics of the individual candidates for the position (candidate risk) and risks external to these candidates (exogenous risk). I then use the model to make specific propositions about how candidate gender affects these risk assessments, and how gender impacts which individuals advance to the executive suite. I test the theoretical propositions related to candidate risk with two experimental studies using different sample populations and experimental designs. The results of Study 1 provide strong support for the general model, demonstrating that moderate-quality job candidates are perceived as more risky than high-quality candidates, and that as a result they are less likely to be hired than high-quality candidates. The results of Study 1 also demonstrate that because moderate-quality women are perceived as less congruent and less committed than equivalently qualified men, they are perceived as more risky candidates for hire than men, and as a result, are less likely to be hired than men. Study 2 provides additional support for my gender- related hypotheses, demonstrating that male participants perceive women as riskier candidates for hire than men and as a result, are less likely to hire them than men. I discuss the implications for both theory and practice.