In the United States (U.S.), women are drastically underrepresented in the role of school superintendent. Women who seek the job face overwhelming barriers and exhibit characteristics different from men causing challenges in obtaining the superintendency. In this study, a content analysis was conducted of the 43 U.S. dissertations relating to women superintendents located in the ProQuest database for the years of 2014-2016. Nine major themes mentioned in a range of 20 to 36 dissertations or (47% to 84%) were discovered: low numbers of women superintendents, gender inequity, history of women superintendents, support systems, career pathways, characteristics of women superintendents, leadership styles, barriers, and school board discrimination. Common themes voiced in 10 to 19 dissertations (23% to 40%) were clustered into the categories of cultural and societal expectations, the glass ceiling, racial discrimination, age, and search procedures. Thirty-five themes were included one to nine times in dissertations (2% to 21%) and considered by the researchers as minor. Displaying issues related to women superintendents highlights concerns and encourages solutions.