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The first chapter explores the relationship between workers' wages and the gender of their supervisor, conditioning on the occupational gender composition. It develops a theoretical model suggesting that supervisors' task assignment accuracy is affected disparately in occupations of different gender types, leading to varying degrees of skill mismatch among workers. This leads to average wage differences between workers with female supervisors and those with male supervisors in occupations of different gender types. Consistent with the theoretical predictions, the empirical evidence suggests that workers have better occupation-skill matches and higher average wages if they work with female supervisors in predominantly female occupations, compared to those with male supervisors; the opposite is true for workers in predominantly male occupations. Although not significant at the early career stage, supervisor wage effects emerge as a worker’s career develops. These findings emphasize the importance of supervisors' task assignment accuracy in workplace gender wage disparity, and underscore the necessity of integrating minority managers to the "gendered" organizational contexts.