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This paper seeks to better understand the ways in which principals select and are selected by the schools they lead. Although we have strong evidence that principals are essential to student success and are systematically sorted into schools in a manner that undermines educational equity, we have very little knowledge of how this sorting occurs. We have compiled an expansive database of leadership applicants, representing the majority of the educator labor market in Wisconsin. By using Correlated Topic Modeling we identify seven types of principals on the job market. This paper presents this typology of leadership along with professional characteristics and organizational factors to characterize the labor market and predict the likelihood of being hired.