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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, government, businesses, nonprofits, and philanthropies to improve population-level educational outcomes (Henig et al., 2015, 2016; Riehl et al., 2019). This paper examines the implementation of one cross-sector education collaboration, focusing on how it works to improve postsecondary degree attainment in its local community. Findings have implications for program implementation in other cross-sector education collaborations and highlight the ways different organizations respond to collaboration to improve postsecondary-related outcomes in their communities.