The ability to collaborate online is an essential skill that allows learners to bring together diverse perspectives to deepen understanding regardless of physical location. As online learning and hybrid workplaces have become more prevalent since the COVID-19 global pandemic, the critical nature of this skill has become particularly relevant for post-secondary graduates. While exams are traditionally viewed as solitary endeavors, collaborative exams offer invaluable opportunities for learners to develop these skills. However, this form of collaborative assessment can be challenging for both learners and educators, and few studies offer guidance for the effective design of collaborative exams. As such, in this paper, we report on the design and implementation of a synchronous collaborative midterm exam in a large first-year undergraduate course. Specifically, we describe how we drew on a theoretical framework of self- and socially shared regulation of learning to design a three-phase exam fostering learners' engagement in key processes of planning, strategic enactment, and reflection on collaboration processes and products. Finally, we discuss key considerations that arose during the design and implementation of the exam, including ensuring an emphasis on process and authenticity, ethical use of video, and equity of access.