This paper aims to identify the factors which might affect secondary school head teachers’ job satisfaction in the city of Jeddah, Saudi Arabia. This study adopts a sequential exploratory strategy based on a mixed methods approach. The qualitative data generated identified the factors leading to job satisfaction and dissatisfaction. The factors fall into eight major themes: relationship with the educational administration, head teachers’ practices, the school environment, relationships with students and parents, head teachers’ authority, relationship with educational supervision and relationships with teachers. The quantitative data reveal that factors causing dissatisfaction are: lack of authority to transfer underperforming teachers, lack of finance and manpower for the cleaning of school buildings, lack of financial resources to improve school buildings, salary, poor revenue from school meals as a financial resource, and lack of financial reward. To explore the relationship between job satisfaction and the selected variables, a Kruskal-Wills (non parametric statistical test) revealed significant differences between job satisfaction in terms of morale, relationship with the educational administration, the school environment, head teachers’ authority and overall job satisfaction according to educational supervision centers. In addition, a kruskal-Wills test revealed significant differences between job satisfactions in head teachers’ practices according to completion of the head teachers’ training programme. However, there were no significant differences between job satisfaction related to experience, student numbers, head teachers’ qualification, age and school building type. The paper identifies that the highly centralised educational system in Saudi Arabia and the lack of autonomy are factors that affect job satisfaction.