Women are underrepresented in medicine and academic anesthesiology, and especially in leadership positions. We sought to characterize career achievement milestones of female versus male academic anesthesiology chairs to understand possible gender-related differences in pathways to leadership. We conducted a retrospective observational cross-sectional analysis. In November 2019, curricula vitae (CVs) were requested from then-current members of the US Association of Academic Anesthesiology Chairs. Data reflecting accomplishments up to the time of chair appointment were systematically extracted from CVs and analyzed using a mixed methods approach with qualitative content analysis supplemented by descriptive statistics and bivariate statistical testing. Missing data were not imputed. Seventy-two CVs were received from eligible individuals (response rate 67.3%). The respondent sample was 12.5% women (n = 9), 87.5% men (n = 63), and no transgender or nonbinary people; this is similar to the known gender balance in anesthesiology chairs in the United States. No statistically significant differences in objective markers of academic achievement at the time of chair appointment were evident for female versus male chairs, including time elapsed between the first faculty appointment and assumption of the chair role (median 25 vs 18 years, P = .06), number of publications at the time the chair was assumed (101 vs 69, P = .28), or proportion who had ever held a National Institutes of Health (NIH) grant as principal investigator (44.4% vs 25.4%, 0.25). Four phenotypes of career paths were discernible in the data: the clinician-administrator, the educator, the investigator, and the well-rounded scholar; these did not differ by gender. Female chairpersons who were members of the Association of Academic Anesthesiology Chairs in the United States demonstrated similar patterns of academic achievement as compared to male chairpersons at the time the position of chair was assumed, suggesting that they were equally qualified for the role as compared to men. Four patterns of career achievements were evident in the chairperson group, suggesting multiple viable pathways to this leadership position.