Indigenous youth are disproportionately represented among youth experiencing homelessness in Canada and are at an increased risk for mental health and substance use problems compared to non-Indigenous youth experiencing homelessness. Research is needed that considers how best to support Indigenous youth in acquiring and maintaining stable housing. Indigenous youth peer mentorship is one possible mechanism that warrants consideration, as Indigenous youth who have previously been homeless can share experience with the barriers that other youth encounter as well as skills that may be well-suited to facilitate hope and understanding to other homeless youth. In the present study, we examined the process by which Indigenous peer mentors engage in a peer-driven project designed to support other Indigenous youth experiencing homelessness in Northwestern Ontario. This process was documented through qualitative interviews with three peer mentors and three staff, as well as ethnographic fieldnotes. Thematic analyses revealed that peer mentorship positions appear to be useful for the Indigenous youth who engage in them, as these positions provide them with a paid avenue to engage in advocacy and support others with similar experiences as them, while simultaneously increasing their cultural connectedness, confidence, self-esteem, self-awareness, and ability to advocate for their own needs. The present study also yielded important considerations for organizations implementing Indigenous youth peer mentorship positions, including offering training and providing opportunities for cultural engagement, avoiding tokenism, being cognizant of possible dual-relationships, and supporting peer mentors who may be grappling with personal difficulties outside of their roles.