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This study investigates the labor market for principals and APs across a diverse range of school district contexts in a single state, with attention to the difficulties school districts face in leader recruitment and hiring and the strategies they use to attempt to overcome those challenges. We take a mixed-methods approach, analyzing administrative data alongside a survey of school district leaders and data from original interviews with two dozen district superintendents about their approaches to the leadership pipeline. Findings suggest a misalignment between the number of leadership vacancies and the pool of actively licensed candidates within each district. While this misalignment can be attributed to numerous factors, districts utilize a variety of strategies to build and sustain applicant pools.