This study seeks to better understand broad management issues associated with the employment of female workers in one sport for development (SfD) project. Through interviews with the executive director and five female staff members of Skateistan—the skateboarding SfD project operating in Afghanistan, Cambodia, and South Africa—this study offers insights on female transmigrant workers who relocated to work for the project in Afghanistan, focusing particularly on how formal and informal management strategies are experienced by international female staff and volunteers. Extending the work of Black, Mendenhall, and Oddou with a poststructural feminist approach, we identify six key themes related to the experiences of female transmigrant workers moving into and during SfD assignments: (a) initial motivations, (b) organizational selection mechanisms, (c) management of risk, (d) work–life balance, (e) managing the self, and (f) negotiating postcolonial critiques of development work. In so doing, this paper recognizes women’s lived experiences as a valid and valuable form of knowledge that could be used to inform management approaches adopted by SfD organizations.