Research examining the teacher hiring process is scant and has largely ignored the principal's role. This qualitative, comparative case study uses Person-Environment fit to explore teacher hiring in two high schools with divergent characteristics in the same district. Findings suggest that fit is a dynamic quality, depending on school context and evolving through the phases of hiring and into job performance. Moreover, the dynamic of fit hinges on teacher experience and subject area taught. Awareness of varied trajectories of fit are crucial to the ability of the principal to design an approach to hiring appropriate to her or his school.