At a time when homelessness, inequality and poverty plague Canadian society, an organization in Whistler, British Columbia has been working for over 20 years to combat some of the associated issues faced by vulnerable youth. This multi-year research project explored one of the programs offered by the organization with the intent of gaining an understanding of the short- and long-term impact, the future requirements for sustainability and growth, and the alignment of the program to local and regional needs. Through a series of focus groups, qualitative data was collected and, while the focus of the research project fell across the identified program foci of housing, employment, participant experience, and support, this article focuses specifically on the findings related to employment. The five themes that were identified in the data collected included: participants’ context, processes to support accountability, contributors to success, challenges, and participants’ suggestions for improvement. Across these themes and sub-themes, it was clear that stable employment is a necessary component of a comprehensive program that supports youth as they build resilience and combat homelessness.