The picture of Canadian women coaches is usually ones who are young, single, without a family, leave the profession within five years or continue at the community or introductory levels, hold part-time positions, and most likely work with women or girls. In this chapter, the authors discuss the career development of Canadian women who coached high performance track and field athletes using an ecological framework. This framework considered influences and supports for one’s experiences from macro to micro levels. First, the authors share their reflections on initiatives to support them as coaches at the system, organisational, and interpersonal levels of sport. Next, they highlight some of the personal strategies they used to remain coaching within the sport system. For each of these levels, the authors offer some suggestions to foster women’s development as elite coaches. Finally, they provide some ideas for future research in this area.