For teens growing up in military-connected families, challenges relating to relocation, parental deployment, and reintegration add layers of stress to an already complex time of life. Out-of-school time programs provide military-connected teens opportunities to utilize existing strengths, develop new skills, and build support networks, as exemplified in the Military Teen Ambassador (MTA) program -- a positive youth development program developed by the Boys and Girls Clubs of America in collaboration with the US Armed Forces. This study investigates the developmental benefits experienced by the teens serving on the MTA Steering Committee -- a youth-adult collaboration designed to plan and deliver the MTA program. Interviews with teen and adult participants were analyzed through the lenses of relational developmental systems theory and a structured evaluation framework. Findings contribute insights into developmental processes and outcomes for programs targeting military-connected youth and provide applied implications that extend to broader youth and adult populations.