This chapter examined the persistent underrepresentation of women in managerial positions within educational institutions, particularly focusing on female teachers in Zimbabwe. The study focused on the factors that influence the upward career progression of female teachers into school leadership positions. Despite the increased participation of women in the labour market, they remain underrepresented in managerial and leadership roles due to a phenomenon referred to as the “glass ceiling” effect. Guided by Socialist Feminism and inspired by Africana Womanism, this qualitative study employed a phenomenological research design to investigate the factors that influence the upward mobility of female teachers into headship and managerial roles. The findings reveal a continuing prevalence of the “glass ceiling” in the educational sector, with several gender-specific constraints limiting women’s occupational mobility and impeding their advancement to headship positions. These factors include among them, the prioritisation of reproductive and family responsibilities which tend to limit the occupational mobility of women. Some of the identified gender-specific factors were found to align with the principles of Africana Womanism, which emphasises the centrality of the family. The findings have practical implications for policymakers and educational administrators seeking to promote gender equity and women’s leadership in the education sector, thereby facilitating their career progression. The study recommends that the Public Service Commission should consider the family commitments of female teachers when deploying them to school leadership positions in order to address the persistent “glass ceiling” in the education sector.