The problem that this study investigated is whether a set of characteristics (gender, age, region, race/ethnicity, and path to licensure) predict the level of interest of principals in pursuing the superintendency. This quantitative, correlational study aimed to address this problem by investigating if demographic factors can predict K-12 principals' interest level in pursuing superintendency, guided by the frameworks of Person-Organization Fit (PO Fit) Theory and Leader-Member Exchange (LMX) Theory. PO Fit Theory suggests that alignment between an individual's values and those of the organization enhances job satisfaction and commitment. LMX Theory explores the relationships between leaders and members within an organization, suggesting that the quality of these relationships influences career development and progression. The study was designed to fill a gap in the literature by examining the impact of age, gender, region, race/ethnicity, and path to licensure on principals' level of interest in pursuing superintendency. The research questions guiding the study are: (1) Do the set of characteristics (age, gender, region, race/ethnicity, and path to licensure) predict the level of interest of principals in pursuing Superintendency? (2) Do any of the predictors (age, gender, region, race/ethnicity, and path to licensure) uniquely contribute to predicting a principal's level of interest of in pursuing Superintendency when controlling for these predictors? A survey instrument consisting of six questions was developed based on the existing literature. The target population for this study includes candidates qualified to pursue the superintendency role. The sample consists of 65 K-12 principals from a southeastern state. The collected data were analyzed using statistics to examine the relationship between the identified characteristics and principals' interest in pursuing the superintendency. Multiple regression analysis was conducted to determine the extent to which the characteristics (age, gender, region, race/ethnicity, and path to licensure) predict principals' interest. Additionally, ANOVA and t-tests were employed to investigate potential differences in interest based on categorical variables, such as gender and region. The findings of this study indicate that all the investigated characteristics (age, gender, region, race/ethnicity, and path to licensure) significantly predict principals' interest in pursuing the superintendency in a southeastern state. Specifically, when controlling for each characteristic, gender and region emerged as statistically significant predictors. These findings, interpreted through the lens of PO Fit and LMX theories, contribute to a better understanding of the factors influencing principals' career aspirations and provide insights for effective succession planning efforts. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]