Collaboration between industry partners and collegiate faculty/students is often a complicated undertaking. In projects that cross departments and include numerous independent groups, the complexity of the overall undertaken tasks can grow significantly. Students and faculty may be involved for various portions of the project that span across multiple courses and semesters. Throughout, independent student roles may vary from small parts on up to central roles in the overall project development. This presents numerous challenges from both academic and logistical standpoints. For this study, the project goal was to take an existing, commercially available electric-assist bicycle and adapt it to include physiological feedback from biometric sensors, in order to prevent injury to the rider. If the identified sensors detect the user may be at risk of injury, through an array of predetermined medical constraints, the bike's motor would automatically take over to limit the physical exertion of the user. Because of the interdisciplinary facets of the project, student groups from different backgrounds were recruited and assigned to specific tasks. In the completion of the prescribed tasks, many obstacles and issues arose. Over three academic semesters beginning in May of 2016, overlapping cohorts of students (17 students total) and faculty (12 faculty members) at Wentworth Institute of Technology entered into a partnership with RRT eBikes. The work presented here describes their roles in a large industrial/collegiate collaboration and provides insights into what worked, what didn't, and the reasons for each. In particular, setting student and faculty roles and maintaining direction with a large cross-disciplinary team proved to have unique challenges. After the initial semester, the team worked to improve the process based on feedback gathered during the intercession. This work describes the iterative process and provides insight into what worked and what didn't in this large-scale interdisciplinary project. It provides tips and tricks for people pursuing similar large scale projects for undergraduate programs, interdisciplinary teams, and/or industry partnerships.