The thesis advanced in this chapter is centred on the ways in which the philosophy of servant leadership fosters gender sensitivity and parity in educational leadership in the South African educational system. The discussion is guided by the following research questions: What are the key constraints in the practice of servant leadership and gender sensitivity in South Africa’s higher education institutions (HEIs)? How can gender sensitivity be incorporated into the practice of servant leadership in HEIs? How can leaders in HEIs synergise servant leadership and gender sensitivity in their day-to-day work life? The basic algorithm of the literature review in this chapter is as follows: introduction; a feminist interpretation of servant leadership; the intersection of servant leadership and feminist theoretical frameworks; the synergy of gender sensitivity and servant leadership in HEIs; key constraints in the practice of servant leadership; factors affecting gender sensitivity in South African HEIs; measures that may help integrate gender sensitivity into leadership in HEIs; and a critique of servant leadership in HEIs. The conclusion and recommendations envisage a wake-up call for leaders in South Africa’s HEIs, urging them to take heed of servant leadership and thus join the move to this leadership style in HEIs, management, and business organisations across the globe.