Youth exposed to high levels of adversity during childhood face major challenges in achieving normative milestones such as securing employment. Effective support holds the potential to significantly change the long-term outcomes for these youth, but there is debate about what programme components are most effective in scaffolding these youth into work. This paper presents findings from a mixed-methods longitudinal study that collected survey data for three years followed by qualitative work with a representative subgroup of youth (n = 107) for a further three years. It explores a subset of data to identify factors associated with positive employment outcomes for these youth (aged 12–17 at study entry). A particular concern was to identify factors that were amenable to intervention in order to provide professionals and policy-makers with evidence concerning the most important programme components and policy settings. Factors that made the most difference to the employment outcomes for this ethnically diverse cohort of vulnerable youth were a history of employment, employment-related skills and access to ongoing support. In addition, male gender and older age played a role in these outcomes. Commonly identified risk factors (substance use, offending) did not play a role, neither did ethnicity, family nor neighbourhood characteristics nor individual strengths. The importance of early exposure to workplaces, opportunities to develop employment skills, and access to ongoing support from at least one positive adult, are key factors for programmes supporting the employment transitions of vulnerable youth.