The main argument advanced in this chapter is that owing to a number of factors, women in South Africa are under-represented in top leadership positions in higher education institutions (HEIs). The discussion is guided by the following research questions: What are the key factors that contribute to women’s under-representation in top educational leadership positions in South Africa’s HEIs? How can this conundrum of women’s under-representation in top Higher Educational (HE) leadership positions be mitigated? And how can gender sensitivity and parity be promoted to boost South African women’s quest for top leadership positions in HEIs? Adopting a conceptual as opposed to an empirical approach, the chapter offers a discussion and analysis of the key factors contributing to the under-representation of women in leadership positions in the HE fraternity. The findings of this study show that despite the proactive efforts of many social institutions (HEIs included) to combat gender bias in their organisations, societal prejudices still disadvantage women leaders and the HEIs that employ them.