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Good teaching matters, especially for students growing up in poverty. But, effective teaching does not alone depend on the contributions of talented and skilled individuals. Rather, promising pedagogues are far more likely to rise to their potential when they are well-matched with both their teaching assignment and with the school organization where they work. Although recent staffing reforms have decentralized hiring and enabled many schools to exercise more discretion in recruiting and selecting teachers, little is known about how individual schools conceptualize and carry out these processes, or how administrators and teachers experience these efforts. This dissertation investigates these issues, drawing on data from a larger exploratory study conducted by the Project on the Next Generation of Teachers. The sample includes interviews with 142 administrators, teachers, and staff in six schools—three district and three charter—that were demonstrating success with low-income, minority students, in the same city. The dissertation includes three papers: A Quest for “the Very Best”: Teacher Recruitment in Six Successful, High-Poverty, Urban Schools; The Matchmaking Process: Teacher Hiring in Six Successful, High-Poverty, Urban Schools; and The Challenge of Recruiting and Hiring Teachers of Color: Lessons From Six High-Performing, High-Poverty, Urban Schools., Culture, Communities, and Education