Over the past four years, the Admission Office at The Hotchkiss School has transformed its student tour guide program into a dynamic ambassador program that drives engagement, supports enrollment strategy, and keeps students actively involved throughout their time on campus. This session is designed for admission professionals looking to move beyond a traditional tour guide model and build a program that students are excited to join and motivated to stay in. Framed around a simple progression (Try It → Love It → Lead It), presenters will share how lowering barriers to entry through shadowing opportunities, low-commitment trial tours, and peer-to-peer recruitment encourages broad participation, while a strong culture of belonging and recognition promotes sustained participation. Presenters will highlight key structures that support this model, including a tiered incentive system, a competitive student leadership pipeline, and a centralized ambassador management system built within Slate CRM. By consolidating applications, scheduling, engagement tracking, and student profiles into a single system, the team has increased efficiency while creating new opportunities for personalization and student ownership. Participants will leave with practical strategies to make their ambassador programs easier to join, harder to leave, and more deeply integrated into the work of their admission office. They will design a tiered ambassador model with leadership pathways and explore ways to leverage CRM systems to streamline ambassador management and improve efficiency. Interactive elements will invite attendees to reflect on their current model and identify opportunities to strengthen student engagement, leadership development, and authentic student partnership in enrollment strategy.