Emerging research indicates that Head Start employees often struggle with health issues and may not be able to model the healthy behaviors that they hope to instill in young children. The purpose of this study was to examine the relationships between perceived physical health and chronic disease, stress, financial resource strain, and job type. Method: This study was conducted in a large, multi-site Head Start agency located across five counties in the American Midwest. Employees (N = 550) were invited to complete a 58-item questionnaire that assessed overall health and health behaviors, demographics, workplace environment, and interest in wellbeing programs. Bivariate analysis and multinomial logistic regressions were used to analyze the relationships between variables of interest and physical health. Findings: More than half (n = 295; 53.64%) responded, and one quarter of the employees (25.42%) reported poor or fair health. Poor and fair physical health was associated with the number of chronic conditions, difficulty paying for basic necessities, and perceived stress, but not job type. A high percentage of responding employees (83.34%) reported interest in wellbeing programs, yet interests varied significantly by health status. Employees with poor and fair health expressed interest in stress and emotional-coping programs, in contrast to the fitness interests of employees who reported good, very good, or excellent health. Conclusion/Application to Practice: To meet the needs of employees with poor or fair physical health, employers should offer health behavior modification programs that address the sources of employee stress, including financial-resource strain and mental health challenges. (author abstract)