Despite the dramatic increase in the number of women and girls participating in sport, data indicate that the majority of sport leadership positions continue to be held by men globally. The Ecological–Intersectional Model provides a basis for understanding the drastic underrepresentation of women in the sports coaching profession. Using this model as a framework, the two cases presented here illustrate examples of the barriers and supports that women experience in pursuit of the sports coaching profession and how issues of power and intersectionality influence those experiences. These cases highlight that although women are essential to advancing the sports coaching profession, several interdependent forces work to suppress the development of women coaches. Students will be challenged with identifying solutions for increasing the number of women in these leadership positions as well as for promoting a positive, inclusive, and equitable coaching environment for women.