This case study examined the collaborations between an urban school district and various entities, as part of their district-wide implementation of high school career academies. Specifically, the study addressed the following research question: How has cross-sector collaboration shaped the development and implementation of career academies in an urban school district? A meta-framework concerning cross-sector collaboration developed by Bryson, Crosby, and Stone (2015) supported data collection and analysis. Findings disclose a complex system of structures and processes to support the district's career academy implementation and reveal how cross-sector collaboration has been critical since its outset. This study provides an initial and important step toward understanding the processes and the leadership required to develop and sustain cross-sector reforms centrally involving schools.