Background: Nascent empirical research demonstrates the sizable impacts of principals on student achievement. More research is needed on the pathways to the principalship and how principals’ characteristics and training experiences influence their performance. Purpose: (1) To describe the characteristics of first-time principals and the schools that hire them and (2) to assess the extent to which the characteristics of early-career principals and the environments in which they previously worked are associated with changes in student achievement in the schools they lead. Setting: North Carolina public schools. Sample: All first-time principals (981 in total) from 2006-2007 through 2009-2010 and the students attending the schools where they serve. Data: Administrative data on students, school personnel (teachers, assistant principals, principals), and schools provided by the North Carolina Department of Public Instruction. Research Methods: Covariate adjustment and fixed effects value-added models. Findings: We find that first-time principals are “homegrown”—hired from within the district. On average, first-time principals wait 5.12 years between completing formal principal preparation and assuming school leadership and spend 4.15 years as assistant principals in North Carolina public schools. Several principal characteristics, including holding a doctorate from an in-state private or out-of-state institution (negative) and serving as an assistant principal in a high–value-added school (positive), are significantly associated with student achievement gains. Conclusions: This study suggests that the effectiveness of early-career principals may be affected by the environment where they served as assistant principals. Further analyses are needed to better understand the attributes of meaningful assistant principal experiences.