This five-week intensive course is designed to equip students with the strategic, operational, and leadership skills necessary to transform healthcare delivery systems. Framed through the lens of a healthcare CEO and tech executive, the course challenges students to develop a mission-driven, financially sustainable business plan that addresses the sector's most pressing post-COVID challenges-ranging from workforce burnout and access disparities to rising costs and declining life expectancy. Central to the course is the integration of artificial intelligence, particularly large language models like GPT-4 and Microsoft Copilot, into healthcare strategy. Students will explore AI's applications in clinical decision support, diagnostics, medical education, scribing, telemedicine, and patient engagement. The course emphasizes the distinction between mere technology substitution and true ecosystem transformation, urging students to leverage AI to reimagine care delivery models. Tools such as the Dartmouth Atlas and Rethink Health simulation are used to analyze care variation and model investment strategies. Case studies from institutions like the Cleveland Clinic, Dartmouth Spine Center, and ImagineCare provide real-world context. The course culminates in a 10-slide strategic presentation to a mock Board of Trustees, with the top plan selected by peer vote. Through this experience, students gain hands-on exposure to data-driven decision-making, strategic forecasting, and change management in a rapidly evolving healthcare landscape.