The 2010 Affordable Care Act provided new impetus and funding opportunities for state Medicaid agencies to integrate community health workers (CHWs) into their health systems. Community health workers are trusted community members who participate in training so they can promote health in their own communities. This qualitative study shares lessons and strategies from Oregon’s early efforts to integrate CHWs into Medicaid with concomitant financing, policy, and infrastructure issues. Key informant interviews were conducted with 16 Coordinated care organizations (CCO) and analyzed using an iterative, immersion-crystallization approach. Coordinated care organizations found CHW integration a supportive factor for Medicaid-enrolled members navigating health and social services, educating members about disease conditions, and facilitating member engagement in primary care. Barriers to CHW integration included a lack of understanding about CHW roles and their benefits to health systems, as well as a need for more intensive guidance and support on financing and integrating CHW services.