Health care in the U.S. and globally continues to undergo massive transformation, surging towards a system that rewards value for patients. However, widespread adoption of value-based health care remains a challenge. This case study focuses on the care delivery transformation undertaken within an academic medical center, with a specific focus on novel payment structures (e.g., bundle payments), integrated practice units (IPUs), and outcomes measurement. Insight into time-driven activity-based costing, or TDABC, and the use of innovative digital health solutions are also touched upon. Leadership challenges and strategic dilemmas are highlighted.