Cross-sector education collaborations, sometimes termed “collective impact” or “cradle-to-career” initiatives, have emerged in recent years across the U.S. as local interventions attempting to align services among educational institutions, local government, businesses, other community-based organizations, and philanthropies to improve educational outcomes. This study utilizes case study methods to focus on how one cross-sector education collaboration, Graduate Tacoma, works to improve postsecondary degree attainment in its local community and ensure equitable outcomes across student groups in the process. Drawing on 26 interviews with organizational stakeholders, internal documents, and a variety of other secondary data sources, the study addresses three facets of cross-sector collaboration implementation: 1) strategies utilized in Graduate Tacoma’s Tacoma College Support Network to address postsecondary readiness, enrollment, and attainment, 2) how those strategies relate to influencing postsecondary-related outcomes and equity in outcomes, and 3) conditions contributing to how those strategies connect to targeted educational outcomes. Findings suggest that strategies are most shaped by organizational missions and leadership of those stakeholders willing to collaborate. Those strategies where the local school district was heavily involved have had the most influence in shaping targeted educational outcomes. The relationships created among collaboration stakeholders also produce other kinds of public value, improving understanding of how sustained collaboration strategies impact organizational responses addressing postsecondary enrollment, attainment, and educational equity concerns. Study conclusions point to conceptual and methodological considerations for researchers in understanding the forces that need to be considered in assessing how cross-sector education collaborations contribute to systemic educational improvements. By describing the challenges and opportunities in implementing this cross-sector education collaboration, this study also has implications for how policymakers and practitioners can leverage school district and other partnerships in their communities for systemic change.