Women continue to remain greatly underrepresented in senior leadership roles, perhaps most obviously within the CEO position. However, the Ontario hospital system is a notable counterexample: 52% of Ontario hospital CEOs identify as women. This begs the question: how did these women ascend to the hospital CEO position? In attempts to explain this anomaly, we leverage existing theory on women in leadership to generate three plausible explanations. Using data from 22 semi-structured interviews with women Ontario hospital CEOs, we employ abductive thematic analysis to empirically evaluate our three explanations. Findings show that communal behaviors positively contribute to women’s upward career mobility, and that the hospital CEO job role strongly entails communal leadership behaviors. Further, throughout their careers, many participants subtly exuded the essence of agency without engaging in traditional agentic behavior. Collectively, overt communal behaviors and subtle agentic behaviors positively contributed to participant’s emergence as CEOs. Ultimately, findings depict a new way in which these women leaders navigated a shifting double-bind.