Head Start (HS) is our nation's largest two-generation program that provides early education services to children and a variety of family support services that may promote economic wellbeing. Yet, no prior research has documented or described the effects of HS on parental earnings. We explore whether the program promotes parental earnings on average, investigate for whom these effects are greatest, evaluate the extent to which earnings impacts vary across HS sites, and identify which characteristics of centers associate with cross-site variation. We find that HS does not improve earnings overall. However, the program does increase parental earnings in a younger program cohort two and three years after random assignment. These effects are larger for single parents and those who are initially employed or in school. Earnings effects are typically homogenous across sites, although we do observe increasing variation over time that reaches statistical significance four years after random assignment. We are generally unable to explain this variation using measures of what HS sites do or provide apart from the economic wellbeing of the families they serve.