It’s tough for a southern kid born at the bottom of the income ladder to get ahead. Overcoming regional economic hardship, long-tolerated racial inequity and subpar education infrastructure is almost impossible. But there is progress. This issue brief examines two key elements connecting southern young adults with rewarding employment opportunities: employer and youth engagement. The brief offers a framework to assess the preconditions for effectively engaging employers and young adults and identifies examples of promising efforts. It also considers what philanthropy can do to reinforce the importance of employer and youth engagement and expand the use of both in the South.