For young parents juggling work, school, and child care, supporting their families while transitioning into adulthood can be challenging. Parents with low incomes and those who have been involved with the foster care or criminal legal systems face even greater barriers to achieving stability. To explore how organizations can improve young parents’ employment and educational opportunities, this blogpost reflects findings from interviews with representatives of three partners involved in the Learn and Earn to Achieve Potential (LEAP) initiative. (LEAP™ is a multimillion dollar initiative to increase employment and educational opportunities for young people, ages 14 to 25, who are in foster care, homeless, or exiting the juvenile justice system.) Interviews were held with staff members at two LEAP cohort members—the Nebraska Children and Families Foundation and The Door in New York City—as well as with Hennepin Healthcare, a Minnesota organization that collaborates with Project for Pride in Living, another LEAP cohort member. The answers they shared highlight the importance of convening cross-sector partners to work toward common goals, connecting with other organizations to meet parents’ basic needs, and navigating public systems to remove barriers and help young people achieve their goals.