The Cleveland Clinic Lerner College of Medicine of Case Western Reserve University (CCLCM) was created in 2004 as a 5-year undergraduate medical education program with a mission to produce future physician-investigators. CCLCM's assessment system aligns with the principles of programmatic assessment. The curriculum is organized around nine competencies, where each competency has milestones that students use to self-assess their progress and performance. Throughout the program, students receive low-stakes feedback from a myriad of assessors across courses and contexts. With support of advisors, students construct portfolios to document their progress and performance. A separate promotion committee makes high-stakes promotion decisions after reviewing students' portfolios. This case study describes a systematic approach to provide both student and faculty professional development essential for programmatic assessment. Facilitators, barriers, lessons learned, and future directions are discussed.