Women’s participation in sporting activity has increased significantly over recent years, though they continue to be underrepresented in management and leadership roles. UK sport faces a similar gender imbalance, and this chapter offers an exploration of this through a research study investigating enablers and barriers to women’s career progression in the horseracing industry. Women across all sectors face a series of career barriers which were also identified within horseracing. These include family responsibilities, perceptions that women are less motivated or capable, limitations due to role segregation or gender stereotyping, and negative perceptions of female leaders. Important career enablers include the development of social and human capital, for example through training, mentoring, and sponsorship. As a response, and reflecting existing, successful business-led voluntary frameworks, a series of industry-led initiatives was developed for horseracing. These included methods to support women’s progression, along with addressing underlying attitudinal barriers to achieve long-term change.