The study presented in this article focuses on three questions: (1) What elements of current leadership models appear most salient in guiding large-scale technology implementation efforts? (2) Which factors affecting the change process seem most important to participants in the context of technology change, and how do they describe them? and (3) What are the distinctive dynamics of change involving technology implementation? The study used an instrumental case study that examined the experience of a community college known nationally as an exemplar for its learner-centered approach to education and integration of technology into pedagogy. The dynamic interaction between technology and higher education, leadership, organization change, and community college environments was investigated by listening to individual perceptions and stories. A qualitative approach was used because this methodology is best suited for analyzing detailed case data in order to frame issues and formulate emerging themes. All interviews were conducted using open-ended questions adjusted in three separate guides (one each for students, faculty, and administrators) to accommodate the different roles of the interviewees. Emerging from the data was a broad array of leadership strategies that was consistent with and broadened the scope of the key dimensions of the Carter and Alfred model.