How do leaders of the scholarship of engagement (SOE) experience and define this field? Although there have been a significant number of reports and national forums, the field continues to experience diversity of understandings and ambiguity in this discourse. To gain insights into these differing understandings of SOE, this study explored the perspectives of a group of elites, exemplars within the field of the scholarship of engagement. Framed in social constructivism, this study explored the exemplars’ socially and culturally mediated experiences, beliefs, and symbolic interactions. Key findings suggested that the exemplars’ journey and their understandings of SOE were interrelated to their current positionality. Two interrelated but different groups emerged from the data, representing a university-centric enclave and a community engagement-centric enclave. These two groupings suggested that they experienced different defining contexts and experiences as well as valued differing influential key terms and meanings for the work and their understandings of the scholarship of engagement.