In the fall of 2016, through research funding from the Northwest Area Foundation, the College Fund began exploring the landscape of workforce education with tribal colleges and universities (TCUs) in Minnesota, Montana, North Dakota, South Dakota, and Washington. Key stakeholders were identified who have knowledge and experience with workforce training programs on reservations: TCU presidents, staff, and students; reservation-based community development corporations (nonprofit organizations focusing on community revitalization); and national grant-makers, both private foundations and corporations, who make investments in this area. When embarking upon the project, the College Fund set out to answer two questions: (1) How can the private sector support TCU workforce programming directly'? Specifically, which workforce areas are the highest priority and which colleges have readiness, interest, solid academic programming, and support of leadership; and (2) How can the College Fund grow in its ability to support TCU capacity building and student services as it relates to workforce training recruitment, readiness, retention, completion, and career success? Based on the conversations and data collected through this project, the College Fund identified four specific ways that first generation workers can be supported to successfully contribute to their economic well-being, as well as that of their families and tribal nations. This article explores those emerging themes in detail.