Recent data shows a continuing trend of gender disparity in leadership positions in tertiary education in New Zealand with men dominating higher levels of employment and advancing at faster rates than women. This study explored the experiences of six academic women who have advanced to leadership roles in New Zealand to examine the role that gender plays in their career progression. It found a range of gendered experiences including negative incidents of sexism and obstacles to advancing. There were also stories of positive experiences of supportive work environments and initiatives such as mentoring that have aided them to gain leadership positions. Participants recognised the complexity of gender issues acknowledging the range of factors and perceptions that influence their experiences in academia.