Community colleges and broad-access 4-year institutions can serve the vital function of increasing educational equity in the United States, but only if they engage in organizational change to address low completion rates. Drawing on qualitative case studies of 6 colleges, this study explored the influence of different types of leadership approaches on the implementation of a technology-mediated advising reform and assessed which types of leadership were associated with transformative organizational change. In-person interviews were conducted with 101 college administrators, faculty, and staff, and follow-up interviews were conducted with 88 participants. Using Heifetz's theory of adaptive change, we found that transformative change requires multitiered leadership with a unified commitment to a shared vision for the reform and its goals. In addition, although we found that upper-level institutional leaders and midlevel project leaders both had important roles to play, the role of midlevel project leaders was particularly vital and complex.