Even though technology has become a key driver in preparing sports management students for an increasingly globalized industry, it is unclear whether the affordances of these technologies contribute to the transformation of the learning environment. The purpose of this study was to investigate how a learner-generated video assessment develops students’ critical thinking and engagement with the theoretical concepts taught in an undergraduate second-year Sociology of Sport course. Data were gathered using a qualitative case study approach. Students found the video assessment enjoyable; it promoted critical thinking and engagement with theory. However, students were less interested in technology-based assessment than the need for courses to align learning strategies and assessment methods to the graduate capabilities required to transform their discipline in the workplace. We argue that it is this alignment that will lead to a transformation in the learning environment and quality student engagement, rather than the video technology itself.