Hiring and retaining appropriate staff is essential for programs serving those who have experienced chronic homelessness. This paper describes specific staffing challenges and strategies from the Collaborative Initiative to Help End Chronic Homelessness (CICH), an 11-site, multi-agency Federal program designed to serve people experiencing chronic homelessness who also have a disabling condition such as substance use or mental health problems. This paper addresses approaches to staffing including team structures, staff supervision, and training. Challenges identified include low pay, high rates of burnout and turnover, limited time for supervision, and multiple staff training needs. This paper also explores specific staffing strategies based on the experience of the CICH sites, and concludes with implications for practice, research, and policy, including recommendations for ongoing staff training, suggestions for future mixed-methods research, and a call for an enhanced focus on strengthening the homeless services workforce.