Despite empirical evidence suggesting the important influence school leaders have on learning conditions and student outcomes in schools, relatively little is understood about the professional pathways they take into their roles. In this descriptive paper, we document the professional experiences, personal characteristics and instructional effectiveness of Oregon's principals and assistant principals between 2006 and 2019. We highlight the diversity of roles educators assume prior to entering school leadership. We find that school leaders who have prior teaching experience in tested grades and subjects do not raise student achievement at substantively or statistically meaningful higher rates than their peers. We document that female principals and assistant principals have become more representative of the teaching workforce, but that there have been almost no changes in the racial/ethnic composition of school leaders in Oregon. Finally, we observe minimal differences in female and non-White assistant principals' time-to-entry into the principalship. Our findings provide insights on potential points of intervention during the educator career trajectory to attract and develop more effective and demographically representative school leaders.