In 2014, the International Working Group for Women and Sport published the results of a study investigating the global progress made within the women and sport movement in the previous 20 years. The report identified that few actions have been taken to recruit, retain and enhance female sports leaders. This chapter addresses a recommendation from this report to increase women’s leadership in sport, by exploring the outcomes of a Women’s Sport Leadership Academy. The study identifies that the development of women sport leaders has traditionally been informed by liberal feminism, and there remain different barriers for women from countries in the Global North to those in the Global South. Recommendations include women-specific initiatives, the need for continued consciousness-raising regarding organisational culture, and enhanced inter-cultural understanding.