Women leaders contribute positively to organizations yet remain significantly underrepresented in corporate leadership positions. While the challenges women face are well-documented, less understood are the factors that shape the experience and success of women who, against significant odds, rise above the glass ceiling. This paper advances scholarship on women and leadership by analyzing the conditions under which women are promoted to top leadership positions and exploring the opportunities and challenges they face post-promotion. We draw on two data sources: comparison of the career trajectories of all women who have ever served as CEO in the Fortune 500 with a matched sample of men CEOs as well as in-depth interviews with women executives across a variety of sectors. Our analysis reveals that women are more likely than men to be promoted to high risk leadership positions and often lack the support or authority to accomplish their strategic goals. As a result, women leaders often experience shorter tenures compared to male peers. We consider the implication of our findings for theory, research and practice.