© 2014 Lippincott Williams and Wilkins. All rights reserved. Women are significantly underrepresented in hospital CEO positions, and this gender disparity has changed little over the past few decades. The purpose of this study was to analyze the career trajectories of successful female healthcare executives to determine factors that generated inflections in their careers. Using qualitative research methodology, we studied the career trajectories of 20 women who successfully ascended into a hospital CEO position. Our findings revealed 25 inflection points related to education and training, experience, career management, family, networking, and mentorship and sponsorship. We found substantial differences in the career inflection points by functional background. Inflections were more pronounced early in the careers of women in healthcare management, while clinical and administrative support executives experienced more inflections later as they took on responsibilities outside of their professional roles. Only two inflections were common among all the executives: completing a graduate degree and obtaining experience as a chief operating officer. More importantly, our findings show that organizational support factors are critical for the career advancement of women. We conclude with recommendations for individuals in an effort to enhance their career trajectories. We also provide recommended activities for organizations to support the careers of women in healthcare leadership.