Collaboration and teamwork are concepts routinely attributed to organizational success and successful change management. Yet often the details of these collaborative experiences are limited to participants in the team involved. In this case study we highlight how a learning experience architect, as part of an organizational working group, could leverage human performance technology (HPT) principles to lead the analysis efforts surrounding an LMS platform change at a professional training organization. Human performance technology is the study and practice of improving productivity in organizations. This includes designing and developing effective interventions, processes, and methodologies that are ethical, results-oriented, comprehensive, and systemic (West, 2018). This article covers the project’s genesis, the project team’s creation, and how the analysis work was carried out. The first author’s unique access to the subject matter of this case study provides the ability to present the project’s analysis phase in the following narrative format. This article’s intrinsic case study represents an exploratory inquiry into a single case, as this article’s conclusions are inherently limited to its scope. Nevertheless, the article provides evidence that large scale change within organizations requires a balance of effective communication practices and organizational systems thinking.