Purpose: We used gatekeeping theory to frame our examination of whether and when educators with superintendent certification become superintendents, and how their likelihood of making that transition is influenced by race, sex, and other characteristics. Furthermore, we sought to identify variation in career pathways to the superintendency. Data and Method: We analyzed 26,071 observations of 4,813 unique individuals, representing the entire population of Texas public school educators who obtained their first superintendent certificate between the 2000-2001 and 2014-2015 school years. We constructed alluvial diagrams to visualize these educators' career pathways. In addition to compiling a life table and visual displays of hazard, we used a discrete-time hazard model to control for individual and contextual characteristics associated with transitions into the superintendency. Findings: Educators are most likely to enter the superintendency in the academic year immediately following that in which they obtained the requisite certification. Furthermore, pathways to the superintendency differ greatly based on educator sex and race, as well as the level and locale employment setting. Finally, we determined that age, experience, education, level of employment, and sex all have statistically significant impacts on the likelihood of becoming a superintendent. Implications for Research and Practice: We discuss the role that researchers must play in coordinating with practitioners to ensure more equitable opportunity for aspiring superintendents. We also emphasize the important role that preparation programs play in preparing candidates for the job market. Finally, we ponder further expansions of similar presuperintendency research, as well as more robust applications of alluvial diagrams.