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High quality preschool can reduce achievement gaps and help children get ready for elementary school. However, research has primarily focused on classroom-level factors that shape children’s experiences. In this paper, we use nationally representative data from Head Start centers and prior educational leadership theories and empirical findings, to explore the role of center directors’ educational background in preschool settings, and specifically, their teachers’ feelings of satisfaction and support. We find that center directors’ field of degree is directly associated with teachers’ feelings of job satisfaction. On the contrary, associations between center directors’ level of degree and teacher outcomes are highly dependent on the amount of teacher turnover occurring at the center.