This study examines the practice of school superintendents in Saudi Arabia in five roles as seen by education supervisors within school district offices. The purpose of the study is to examine the leadership of school superintendents in these five roles: work environment, rules and regulations, implementation of technology, accountability, and professional development of the education supervisors in school districts. The study sample consists of 276 education supervisors working in 30 school districts. The study reveals that the respondents (education supervisors) perceived leadership roles enacted to a low degree for the five roles. The final results show that school superintendents’ leadership needs to be developed in order to provide a high quality of education, by improving the selection of superintendents and offering better training in the five roles. The Ministry of Education should decentralize major decisions to school superintendents so that they can be active in leading change and perform leadership roles in their school districts.