Previous research shows that gender vanguards (individuals who demonstrate gender-atypical skills and behavior) suffer backlash in the form of social and economic penalties (Rudman & Phelan, 2008). This study examined backlash against female and male job applicants who were either gender-atypical or typical. Professionals (N = 149) evaluated female or male managerial applicants for internal promotion described in their performance review as showing either self-advocacy or advocacy on behalf of their team. Atypical, other-advocating men were judged to be low on agency and competence and penalized with job dismissal. Serial mediation analysis demonstrated that, compared with other-advocating women, other-advocating men were perceived to lack agency, which contributed to a perceived loss of competence that ultimately led to greater penalties. The implications of these findings for contemporary leadership theories and men’s and women’s professional success in the workplace are discussed.