Gameful digital applications have been adopted in higher education to help increase student engagement and improve learning. However, many studies have only evaluated educational applications that combine some common game design elements—such as points, leaderboards, or levels. Consequently, we still lack studies exploring different ways of designing gameful learning experiences. Therefore, we introduce the design and implementation of a digital system employing a skill tree to mediate instructor feedback and assignment grading in a university course, Additionally, we present the results of a pilot evaluation with 16 students in which we summarized the positive and negative aspects of the experience to derive lessons learned for the use of digital skill trees in similar contexts. Finally, we suggest topics for further investigation.