Gender leadership and pay differentials continue to plague women employed in the male-dominated Canadian transit industry despite focusing on equal pay and gender equity strategies. We conducted a sequential mixed-method study of Canadian women within the transit industry to help elucidate the hidden contextual, social, and organizational factors contributing to persistent gender disparities. For the qualitative phase of the research, women in senior leadership positions (n = 9) participated in semi-structured interviews guided by and analyzed using grounded theory (Charmaz, 2014). The interview results informed the quantitative phase where women in various roles within the transit industry (n = 50) completed online surveys measuring experiences at work, performance evaluations, and opportunities for professional growth. Our results support the exacerbating role of meritocracy that helps explain continued constraints and barriers for women from attraction and retention to promotion and leadership. Women are pressured to conform and perform, often at the cost of authenticity, opportunities for advancement, and well-being to survive within meritocratic establishments in order to ascend into C-Suite jobs. The results of this study have practical implications for transit service organizations that are enacting Equity, Diversity, and Inclusion strategic plans.