A project in Oregon to improve the work of elder caregivers in community-based settings is a timely response to the convergence of several pressing factors: an aging population, growing demand for community-based alternatives to nursing homes, the more complicated care needs of today’s elders, and an increasingly prescriptive regulatory setting. This case study details the development and impact of Jobs to Careers in Community-Based Care, a collaboration among Portland Community College, five Portland-area assisted living facilities, and two health care industry associations. The project is one of seventeen in Jobs to Careers, a national initiative that is creating ways to support the career development of frontline health care workers by blending education and work.