Purpose <p><?tk 3?>To delineate the demographic and structural composition of surgical education leadership and evaluate representation narrowing across the clerkship, residency and fellowship levels as seniority increases along the general surgery training continuum.</p> Methods <p><?tk 3?>A cross-sectional analysis of U.S. surgical education leadership was conducted for the 2025–2026 academic year. The cohort encompassed clerkship directors (CDs, <i>n</i> = 179), general surgery residency program directors (PDs, <i>n</i> = 366) and fellowship directors (FDs) in complex general surgical oncology (CGSO, <i>n</i> = 35), surgical critical care (SCC, <i>n</i> = 134), minimally invasive surgery (MIS, <i>n</i> = 153) and endocrine surgery (ES, <i>n</i> = 25). Data were derived from publicly available sources and national accreditation databases. Pipeline demographics spanning medical school applicants and matriculants (AAMC FACTS, 2022–2025), general surgery residency applicants and matched residents (NRMP, 2022–2025) and subspecialty fellowship cohorts (NRMP SMS, AAES, Fellowship Council) were compiled for contextual benchmarking. Demographic characteristics were ascertained using automated facial analysis with investigator adjudication (Betaface API, version 2.0; Kirchheim bei Munich, Germany). Categorical variables were compared using Pearson χ² or Fisher exact tests. Multivariable logistic regression identified factors independently associated with leadership roles. Analyses were performed using STATA (version 18E; StataCorp LLC, College Station, TX).</p> Results <p><?tk 3?>Among the director cohort (<i>N</i> = 892), White surgeons predominated (67.8%), followed by Asian (18.2%), Middle Eastern (5.3%), Hispanic (4.8%) and Black (3.9%) surgeons. Female representation varied significantly by subspecialty (<i>P</i> &lt; .001); overall representation was 34.5%, lowest in MIS (20.3%) and highest in ES (48.0%). Asian surgeons were most represented among FDs in CGSO (31.4%) and ES (24.0%). International medical graduates were most prevalent among directors (<i>P</i> = .029) in CGSO (20.0%) and MIS (18.3%). Academic rank differed markedly across leadership tiers (<i>P</i> &lt; .001). Assistant Professors constituted the plurality of CDs (44.1%). Full Professors were most common among FDs in CGSO (40.0%) and MIS (33.3%). Institutional setting also varied (<i>P</i> &lt; .001): PDs were predominantly community-based (58.8%) and FDs primarily university-based. Pipeline benchmarking (2022–2025) across 214,411 medical school applicants to 5988 matched general surgery residents, alongside subspecialty fellowship cohorts, demonstrated that women accounted for 56.8% of applicants and 55.1% of matched residents, with Black trainees at 9.4% of matriculants and 7.2% of matched residents, and Hispanic trainees at 6.4% of matriculants and 12.0% of matched residents — proportions exceeding their representation in surgical education leadership.</p> Conclusion <p><?tk 3?>Surgical education leadership remains demographically imbalanced as representation of women and underrepresented in medicine groups narrows progressively with increasing academic seniority, particularly at the fellowship director tier, where leadership is most university-concentrated. Although women are the majority of matched general surgery residents, and Black and Hispanic trainees account for larger proportions of residency entry than of director roles, these gains are not reflected at higher tiers of surgical governance. The discordance corresponds with demographic consolidation within senior academic ranks and university-based institutions across the surgical training continuum.​​​​​​​​​​​​​​​​</p>