All types of healthcare providers depend on medical directors to oversee clinical operations and consult with administrative leadership on facility, unit, or clinical service line plans and performance. Medical directors function at the intersection of administration and clinical care, weighing in on matters as varied and important as accreditation, capital expenditures for equipment, staffing, standard operating procedures, and peer review. In addition to clinical skills, they ideally need excellent people skills to balance competing priorities and communicate effectively with different stakeholders. They are a valuable resource and partner for compliance professionals. With proper support, medical directors can support an organization’s compliance efforts and help mitigate risk for both employee issues and healthcare regulatory matters. This article outlines five key best practices in contracting for medical director services: