This study examines the transformative experiences of a group of academic coaches who participated in the Target New Transitions (TNT) program during the 2014–2015 academic year. The TNT program trains undergraduate students, through professional development workshops and reflective exercises, to serve as year-round academic coaches for first-year students in Chicago’s most impoverished high school districts. Semistructured interviews were conducted with 20 academic coaches in order to understand the transformative nature of the program in relation to social justice learning, translatable skills and values, and career development. Findings demonstrate that significant learning occurred in relation to coaches’ awareness of social justice issues, including issues of power, privilege, and systemic causes of inequality; that learning was translatable to other academic and nonacademic settings; and that many students developed greater commitments to public service careers. Implications are also presented for colleges interested in further anchoring their institutional commitments within their local communities.