In 1981 the National Collegiate Athletic Association (NCAA) developed the designation of Senior Woman Administrator (SWA) within the membership. With the addition of women's athletic programs in the NCAA starting in the 1981-1982 season, the NCAA knew there was a need to guarantee at least one executive woman was seated at the decision-making table to support the new female teams ("NCAA SWA brochure," 2011). Title IX legislation was already a decade old when the NCAA added women's teams and the platform to grow women in sport was forefront (Glazor-Raymo, Townsend, & Ropers-Huilman, 2000, p. 184). Today, there are women in leadership roles throughout intercollegiate athletics, but with all the opportunities that exist there is still a predominately male dominated presence at the highest executive level (Lapchick, 2014, p. 1). For example, today only three "Power 5" female athletic directors out of sixty-five opportunities exist (Macur, 2015). This study will use a phenomenological approach, to interview top ranking women that hold executive level athletic leadership positions to describe in depth their "lived experiences" of rising to leadership positions in a predominately male, competitive environment.