With the desire to expand work-integrated learning opportunities for Canadian postsecondary students, it is timely to consider how pre-existing student work positions may be transformed to achieve the educational criteria and benefits of work-integrated learning. The purpose of this study was to explore the impact of structured learning support on student professional development and workplace performance in the University of Toronto Work Study program. A survey was administered with 716 work study students and 197 campus employers. It was found that students whose supervisor had them set learning goals, conduct a mid-point check-in and a final reflection of their learning goals, scored significantly higher on a series of professional-development related statements compared to students who did not receive the learning supports. Positive feedback on the impact of the structured learning supports on students' workplace performance was also reported by campus employers. Applied recommendations are proposed along with questions for future research.