Academic medicine has made substantial progress toward gender parity among faculty in medical schools and teaching hospitals over the past several decades. Yet women remain underrepresented in leadership positions in academic medicine, particularly at the highest rungs. Disparity in leadership representation, which is incompletely understood, is a national issue because it has implications for talent entering the healthcare workforce and our ability to strengthen the broader health system. This Analysis in Brief presents a snapshot of the percentage of women in leadership positions in U.S. medical schools. Gender differences in faculty rank progression and promotion rates are also examined, as this progression represents a typical career path to leadership positions. Results show, for example, that the percentage of women in positions of leadership has increased over the past 10 years. The proportion of women in the lowest ranking leadership positions is relatively high, though, while the proportion of women in the highest ranking leadership positions is relatively low (Table 1). Results also show that promotion rates differ between men and women. The results of this AIB can help institutions understand where women are getting caught in the academic medicine leadership pipeline as they strive to increase and intensify interventional strategies to achieve gender parity in academic medicine in the 21st century.