While the evaluation of learning development interventions needs to be considered carefully and included at the curriculum design stage, there is limited literature on the actual design of interventions, especially on how these designs evolve and improve over time. This paper describes the evolution of a learning development program intended to support first-year medical students adjusting to a problem-based learning curriculum. We used a design-based research approach, articulating our theoretical grounding and incorporating students’ voices to develop an “optimal” intervention for the specific challenges in our context. We describe lessons learned around four aspects: students’ growth and development, teachers’ professional growth and development, program design principles, and the emergent components of a learning development program. Overall, our students describe the Learning Success Program as adding value by enabling the adoption of a repertoire of skills and strategies for learning management. Additionally, the incremental nature of design-based research allowed for the development of a context-specific program that considers students’ voices through needs assessment and feedback on the program offerings. It has also provided an opportunity for the professional development of teachers through feedback from classroom practice, reflection, and the literature.