Employment social enterprises incorporate a business mission of financial viability into a transitional jobs model structured to help individuals with employment barriers gain unsupported employment. We assess which factors contribute to their success using a cross-case analysis of qualitative and quantitative data from eight enterprises. Results suggest that more successful enterprises built transitional jobs programs that made soft skills training a central component of support and provided structured intensive job search and job placement supports. Results further suggest that integrating a transitional jobs program into a business could enhance the program by helping to (1) create a real-world work experience for participants, (2) focus transitional jobs in low-skilled work and soft-skills development, and (3) boost support services through supervisor engagement and economies of scale.