This qualitative study investigated the scarcity of females in the superintendency in the U.S. public school systems through the lens of the little-studied female assistant superintendent. Females remain underrepresented in the superintendency, with very little change in the last century. While 76% of the K-12 educators in the United States are female, only 22.6% of superintendents are female. To understand this issue, the researcher conducted a constructivist, grounded theory study, framed within social role theory and feminist standpoint theory. Through semi-structured interviews, 12 female assistant superintendents in a metropolitan area presented the barriers, motivators, and relationship they have had with power as they climbed the career ladder. After interviewing the participants, the data revealed collective trends. Analysis indicated that these women had to be "okay" with choices made and how it impacted them, personally and professionally. Motivation and leadership qualities were evident for these women at a young age, and for most, their families encouraged and supported them as they pushed for excellence. These women spoke of influence by others and influence of others. Many had been "tapped by others" to move into leadership roles; in turn, they were motivated by empowering others. It can be concluded that barriers, including gender bias, stereotypes, cultural norms, social roles and expectations of what a female can and cannot do in terms of leadership, play a large part in the scarcity of women in the superintendency. Further research in the area of gender studies and cultural norms is necessary, along with more research into the superintendency from the male's perspective. Continued research could lead to more innovative and inclusive leadership and hiring practices, and mentorship programs, which could increase the numbers of females in educational leadership roles, including the superintendency. Although advances have been made for women in the last 30 years, a pervasive problem remains that cannot be ignored as the number of women qualified for the superintendency is well below the number of women achieving this role. This problem is present in other sectors aside from education, as highly qualified women continue to be underrepresented in positions of power. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]