Population health experiences have become more common in medical education. Yet, most resident population health experiences are in patient panel management and fail to connect with the rapidly growing movement of cross-sector, data-driven, and community-led initiatives dedicated to improving the health of populations defined by geography rather than insurer or employer. In this Perspective, the authors present a five-stage framework for residents' participation in the work of these initiatives. The five stages of this framework are (1) organize and prepare, (2) plan and prioritize, (3) implement, (4) monitor and evaluate, and (5) sustain. In applying this approach, residents stand to acquire new population health skills and augment the value and meaning of their work, while institutions stand to improve the health of the communities they serve, including the health of their own employees. However, a paucity of experienced role models and demanding residency schedules present significant challenges to residents effectively partnering with the community. Residencies and institutions will have to be flexible and committed to being a part of these cross-sector, data-driven, and community-led partnerships over the long term.