Today's superintendents face increasingly non-routine and complex problems that are educational, managerial, and political in nature. This study investigated occupational stressors and job satisfaction of school superintendents in Pennsylvania. This was accomplished through self-report of superintendents and through the perspective of school board presidents. The dissertation employed a mixed method approach consisting of an online survey and follow-up phone interviews of two superintendents and two school board presidents to investigate occupational stressors and job satisfaction of Pennsylvania school superintendents. Research has suggested that internal and external policies and politics affect the occupational stress experienced by the school superintendent. Concerns about funding and the challenge of staying current with state and federal mandates were identified by the respondents as two primary influencers of stress. Multiple regression analyses were used to predict the impact of occupational stressors on job satisfaction of superintendents. It was found that as occupational stress increases, there is significant likelihood that job satisfaction decreases. This translates to increased stress not being mitigated by either appreciation, recognition, or (financial) rewards. Knowing this, policy makers, scholars, and professional associations must be empowered to continually review current practices and provide additional and contemporary professional development initiatives for new and experienced superintendents. The increasingly complex responsibilities of leading school districts in an ever changing environment also requires personnel preparation programs to appropriately adjust their methods of instruction to satisfactorily prepare superintendents for the challenges they face. To further expand on the impact of stress on job satisfaction future research efforts could explore the development of a focus-group-based project that would involve superintendents, school board presidents, and other stakeholders responding to some of the findings generated by this study. [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/en-US/products/dissertations/individuals.shtml.]