Characterization of leadership within otolaryngology is key to evaluating trends and promoting program advancement. This study evaluates representation of women in otolaryngology holding residency and fellowship directorships, or chair positions, comparing sex differences in academic rank, years in practice, and scholarly activity.Cross sectional analysis.A comprehensive list of otolaryngology residency and fellowship directors from Accreditation Council for Graduate Medical Education-accredited programs in 2017 to 2018 was compiled. Academic rank and years in practice were determined from departmental websites, with online search tools used as secondary resources. The h-index was utilized as a measure of research productivity. Regression analysis was performed to analyze these variables.Among the 306 directorships, women held 57 (18.6%) of these positions, 27 (26.5%) residency and 30 (14.7%) fellowship directorships. Of the 99 chair positions, five (5.1%) were held by women. The majority (53.6%) of male directors were full professors, whereas only 26.3% of females were full professors (P = .04). Mean years in practice for female directors (13.9 ± 6.8) was less than that of male directors (20.3 ± 9.4, P < .0001). Similarly, mean h-index for female directors (11 ± 7.2) was lower than for males (17.5 ± 12.5, P = .0001). After controlling for academic rank and years of practice in a multivariable regression, the h-index remained lower for women than for men (P = .03).Women are disproportionately underrepresented in positions of residency and fellowship directorships, and chair positions, consistent with other specialties. Women in leadership had lower academic ranks, fewer years of practice, and lower h-indices than their male counterparts. This may represent a shift in academic otolaryngology as female otolaryngologists seek early involvement in leadership.4 Laryngoscope, 2019.