Women remain underrepresented in positions of leadership throughout the sport industry. This underrepresentation has been previously linked to a leaking pipeline of successful female candidates and over the past five years the proportion of National Collegiate Athletic Association (NCAA) women assistant coaches has declined. Subsequently, occupational turnover intentions of women assistant coaches have been found to exceed those of their male counterparts. Therefore, the purpose of this study was to examine the experiences of former NCAA women assistant coaches who voluntarily engaged in occupational turnover. A qualitative approach, with the theoretical underpinnings of phenomenology and hermeneutics directed the research design. Semi-structured interviews were conducted with 12 participants. Based on the experiences of the participants, these findings extend the body of knowledge concerned with combating the leaking pipeline of women sport leadership candidates. Implications are discussed along with future research suggestions.