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We explore the job application patterns and hiring dynamics in the superintendent labor markets in Wisconsin. Drawing on the framework of labor supply and demand in the educator labor markets, we analyzed longitudinal statewide vacancy-application data with administrative staffing records and district demographics, using regression models with vacancy/year fixed effects. Results show gender and race/ethnicity gaps in the process of job application and hiring. District characteristics are related to an increase in the size and diversity of the application pool, and leadership experiences and being an internal candidate greatly increase applicants’ hiring probability. This study provides implications for diversifying the superintendent pipeline across the stages, recruiting/tapping home-grown potential leaders, and increasing the size/diversity of the superintendent application pool.