Men continue to outnumber women in public school superintendent roles by a 4:1 ratio. However, women outnumber men by a 4:1 ratio in teaching roles in public school districts. In addition, more women than men hold superintendent certificates and educational doctorates. Due to this puzzling discrepancy, it is important to understand possible factors in the form of gendered barriers to access that could lead to the unequal representation of women in superintendent positions. In this study, I examined how these barriers manifested in the experiences of female superintendents participating in the study, how they influenced the hiring experiences of these participants, and how they impacted these female leaders throughout their careers. With this study, I investigated barriers associated with holding mechanisms, gendered norms, and gendered filters that may limit women's access to superintendent roles. Women's experiences of the origins and effects of gender normative perceptions and hiring practices have potential for contributing to the study of gender equity in the field of education and beyond. Findings could provide implications for increasing women's opportunities to serve beyond central office positions in public school districts. Possibilities exist for identifying practices in organizations that have hired women to serve at the highest level of school district leadership; that of the superintendent of schools.