Background: Wilderness therapy (WT) has become a popular method of intervention with youth residing in residential facilities (RFs), and an important part of their treatment plan. Thus, the dual positioning and role of RF staff members - who both accompany participants on the WT journey and, at the same time, participate in their on-site, daily therapeutic processes - becomes pivotal in therapy programs for this population. Purpose: To examine the meaning of RF staff members’ role in supporting youth from RFs during the WT process. Methodology: The study adopted a qualitative-phenomenological approach, anchored in semi-structured, in-depth interviews with 12 therapeutic-educational workers (6 social workers and 6 youth workers) employed in RFs in Israel. Findings/Conclusions: Three roles emerged from the interviews: the witness, the mediator, and the promoter of the treatment plan. Implications: An ecological-systemic approach is recommended. This approach will provide an opportunity for the RF team members to engage in possible interventions during the journey. It will also allow them to expand the change process which takes place on the WT journey, to the daily treatment plan of the youth within the RF, and among the social and educational systems in which they are involved.