Women on the Road to Health Transitions combines two evidence-based strategies, WORTH and Transitions Clinic Network into an intervention for women involved in the criminal legal system with substance use and HIV risks. Led by peer community health workers (CHWs), Women on the Road to Health Transitions also links participants to primary care. We describe the impact of the program from the perspective of the CHWs. As integral research team members, the CHWs learned to successfully recruit, retain, and empower participants, facilitate the intervention, administer surveys, and help them link with and navigate the healthcare system. Simultaneously, the CHWs developed professional skills and self-efficacy.