A propensity for risk taking by men has been used to explain gender gaps in power, mobility and success. Women who embrace risk, however, are in the precarious position of balancing gender norms and career ambition. This study examines gender stereotypes of risk-taking versus the organizational risk-taking realities that are inherent in women corporate leaders’ climb to the top. We take the position that women who have reached top corporate positions must embrace risk. We analyze data that includes all S&P 500 executives and directors covering the period 2009–2019. Findings suggest that corporations led by women CEOs and corporations with greater numbers of women executives and directors undertake more financial risk than those led by their male counterparts. The implications suggest that women may face a significant risk tax in order to overcome gender stereotypes that limit career mobility.