Resident assistants can be a key resource in institutional efforts to promote holistic student success. Historically, higher education institutions have not always activated this resource on behalf of promoting academic success specifically. This qualitative interview study explored how peer residential staff (N = 40) at one large public research university with a specific focus on increasing student success understood and enacted their role in this effort. Findings indicate that participants identified four roles (older sibling, friend, resource provider, role model) through which they enacted proactive, holistic facilitation of a broad construction of the term student success. Participants identified several barriers to and facilitators of their roles in student success, from which I developed recommendations for practice and research.