Students and youth receiving Supplemental Security Income (SSI) often encounter challenges during the transition process due to the added complexities of family poverty, health conditions, and systemic inequities (Hemmeter, 2014; Honeycutt & Livermore, 2018; Wittenburg & Loprest, 2007). Through the multiple phases of recruitment and enrollment in the Wisconsin Promoting the Readiness of Minors in Supplemental Security Income (WI PROMISE) demonstration project, youth and families were more likely to engage with those with similar lived experiences in their home communities. As a result, integrating a new position of family advocate or navigator into the transition process for youth receiving SSI benefits may be beneficial in helping youth and their families successfully navigate the transition process and increase engagement in vocational rehabilitation (VR) services. This study investigated WI PROMISE family advocates’ views of their supportive role, families’ strengths and needs, and challenges that emerged as they supported families during the transition process. Results indicated three key themes: (a) the importance of building trust and raising expectations; (b) effective partnership, accountability, and teamwork across systems; and (c) peer-based roles as coach, mentor, problem solver, and navigator.