People who are homeless experience many barriers that affect their ability to gain and sustain work. In this study, we investigate whether personal job coaching support contributes toward employment success. This study found that clients being supported by a job coach have significantly higher chances of gaining employment than those not being supported. This holds particularly true for the youngest age-group. Furthermore, results also indicate that job coaching improves clients’ chances of successfully sustaining employment. Personal approaches and individual coaching seem to be promising strategies in social work practice and specifically in return to work programs for people who have experienced homelessness.