This article examines the objective facets of CEO careers in family and non-family firms. Optimal matching analysis coupled with cluster analysis are used to show how careers are shaped by different factors in family and non-family firms. We have three central empirical concerns. First, are there distinct patterned trajectories in careers leading to the CEO position in family firms? Second, what is the impact of structural variables such as firm size, ownership structure, geographical location on career prospects? Third, are there functions or mobility patterns that can clear the route to the executive suite in family firms? Our analysis suggests which career patterns are more likely to be conducive of the promotion to the CEO role in family, vs. non-family firms. They suggest that family firms do not conform to the stereotype of promoting only family-related managers following a career within operational functions. Our results have implications for the literature on family firms management and entrepreneurial behavior.