Unfamiliarity with adaptive courseware and its uses may be a barrier to implementation. This article provides insights from a qualitative case study that was conducted to illuminate experiences and perceptions of faculty and staff involved in an adaptive learning technology pilot at a nonprofit university in the United States. Findings revealed that team dynamics, including diversity and persistence, were critical for the success of the project and overcoming the challenges of working with a vendor in terms of process, timeline, and role clarity. Finally, the study helps to underscore the importance of using adaptive courseware to support and train faculty.