The Division of School Leadership (DSL) manages and builds the capacity of superintendents and principals across New York City Public Schools (NYCPS). This capstone presents a detailed glimpse into my strategic project as a doctoral resident in the DSL. The project sought to answer the question: "with no formal team or budget, how does the DSL create a sustainable strategy that improves New York City's historically underperforming public schools on an absolute scale?" I found the solution in the superintendents. Unlike other school districts in the United States, NYCPS superintendents shoulder a unique responsibility. Serving nearly 900,000 students across 45 districts, they act as the chief executive officer of their respective districts and middle managers in the largest school system in the United States. When David Banks was appointed chancellor of NYCPS in January 2022, he reimagined the role of superintendents, giving them more authority, funding, and human capital. The superintendents' increased power and resources place them at the center of my theory of action. My strategic project involved designing a comprehensive, coherent, and differentiated strategy for how the DSL would support superintendents and their teams in improving all schools across New York City. What started as a separate plan for how the DSL would improve historically underperforming schools evolved into the primary strategy for how the DSL central office supported the entire NYCPS system. The capstone narrative describes the research that guided my strategic project, my achievements and setbacks, the underlying causes, and the extent to which NYCPS is on a path toward transforming the educational experience for all students. While the lens of this capstone spotlights the work of developing a citywide school improvement strategy, it also exposes how the limitations of an extensive system work against the progress leaders are trying to achieve. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]