In an effort to simplify the advising and registration process and provide students with a more intuitive enrollment experience, especially at orientation, the University of Wisconsin-Madison's Office of the Registrar and Office of Undergraduate Advising co-sponsored a project to transform the enrollment experience. Using design thinking has helped the University of Wisconsin-Madison's Office of the Registrar solve its most complex problems. This article provides an overview of efforts using the methodology, with a focus on usability, to produce an intuitive enrollment experience that aligns with student and institutional goals. In accordance with the iterative design best practices and design thinking methodology, the authors analyzed the feedback provided during the testing phase and refined the enrollment application prior to introducing it to the incoming 2017 undergraduate class. Observation of advisor-student interactions at the orientation sessions has revealed that advisors are spending less time instructing students how to use the enrollment tools and are able to have more meaningful conversations around course selection. The enrollment experience project highlights how design thinking can enhance an enrollment team's ability to develop great solutions with a focus on the user.