Health care simulation is a rapidly growing, heterogeneous field requiring expertise that is not traditionally represented within health care or educational institutions. Simulation staff members often take on unique roles and have goals and career development needs that differ from more typical hospital and educational institution-based personnel. This poses both challenges and opportunities for simulation administrators. In this article, we describe a novel simulation, Simopoly, designed to provide the opportunity to think creatively about simulation center staff development, retention, and promotion in the context of daily operations and management.