The Shelby County iZone is a district-led effort to dramatically improve, or “turn around,” 23 of the lowest performing schools in Tennessee in the 15th largest district in the country. Despite circumstances that have derailed many past reforms, iZone schools have made statistically significant and educationally meaningful gains in mathematics and English language arts (ELA) (Zimmer, Henry, Kho, & Viano, 2015). This report presents the findings of a multi-year research project that examined the evolution of the iZone as it shifted its strategy from school-level autonomy to one that featured a common curriculum, shared pedagogy, and collegial learning. The analysis delves into the challenges that iZone leaders, principals, and teachers confronted in coping with the needs of a student population mired in intergeneration poverty, rigorous performance standards, and a stringent accountability system. The results illuminate the importance of multi-level system re-design, continuous improvement, and compromise and negotiation among key stakeholder groups.