This practice brief examines the diverse roles that supervisors play in the professional development of their employees, and how differences in these roles can affect program implementation and success. It also demonstrates how Jobs to Careers projects have adapted these roles and functions to a wide variety of health care settings, differing in location, scale, complexity, type of care, financing, and organizational structure. The choices that these employers and their educational partners make offer lessons for the development of new programs to train and advance workers through work-based learning—a cornerstone of Jobs to Careers.