AbstractWhile women’s higher education enrollments and graduation rates have outpaced those of men in the United States and most countries around the world, women are less frequently included in academic leadership roles, including the higher education presidency. This paper asks what predicts whether and when a higher education institution has its first woman president, conceptualizing this event as a milestone of gender equality. We use a national probability sample of 234 four‐year U.S. universities and colleges, constructing a novel longitudinal dataset from 1980 to 2018. Employing event history analysis, we examine the potential mechanisms associated with when an institution has its first woman president over time. Our findings suggest that the demographic diversity of faculty and students, gender‐ and diversity‐supportive structures, and the broader environment in which institutions are embedded predict the likelihood that a woman will advance to the level of the presidency. In particular, the presence of gender studies programs and a higher proportion of women in state legislatures increase the likelihood that an institution will have its first woman president. At a time of growing challenges facing U.S. higher education, coupled with greater opportunities from having more diverse students and faculty, universities and colleges increasingly recognize the benefit of women leaders.