This study explores the educational preparation and career pathways of the chief alumni relations officers at 2015 U.S. News & World Report Top 25 Public Universities in order to determine why women remain underrepresented in these roles. Through the theoretical frameworks of liberal feminism, social comparison, equity theory, and signaling theory, interviews with 10 sitting chief alumni relations officers were complemented by document analyses in order to provide a comprehensive overview of the challenges facing the profession at large. These leading alumni relations professionals offer their views of present and future conditions for those interested in pursuing a career in the field. Special emphasis was given to the discussion of potential programs and initiatives that would have the goal to attract more women to the top leadership positions within alumni relations. The paper concludes with suggestions of related areas which warrant further study.