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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 semistructured 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.