Despite increases in the percentages of women medical school graduates and faculty over the past decade, women physicians and scientists remain underrepresented in academic medicine’s highest-level executive positions, known as the “C-suite.” The challenges of today and the future require novel approaches and solutions that depend on having diverse leaders. Such diversity has been widely shown to be critical to creating initiatives and solving complex problems such as those facing academic medicine and science. However, neither formal mentoring programs focused on individual career development nor executive coaching programs focused on individual job performance have led to substantial increases in the proportion of women in academic medicine’s top leadership positions.