As school districts, major cities, and entire states in the United States adopt personalized learning as a reform strategy focused on the co-construction of learning opportunities between teachers and students, educators face shifting roles. This study examined the roles of teachers in personalized learning environments within a policy context of statewide legislation of personalized learning plans, flexible educational pathways, and proficiency-based assessment. The study used data from interviews with a purposefully selected group of 20 elementary and middle school teachers from 11 schools. Findings revealed teachers' perceptions of their roles as (a) empowerers, (b) scouts, (c) scaffolders, and (d) assessors, as well as associated strategies within each role that participants perceived to be constructive. The use of role theory illuminated the potential for intrarole conflict and role strain between and among these roles along with the cultural dimensions of the shift to personalized learning.