Small to medium enterprises (SMEs) in the food industry contend with a variety of corporate sustainability and social responsibility (CSSR) issues, ranging from the environmental impact of food waste to human health concerns about specific ingredients and production methods. In this qualitative multicase study, based on the conceptual frameworks of strategic development, stakeholder management, and institutional theory, I explored barriers and enablers for Washington, DC-based food SMEs as they proactively addressed CSSR issues. I interviewed five SME owner-managers. The transcripts were then coded and analyzed. Three themes emerged. Strategic development tended to be ad hoc and experimental, but with equal focus on establishing and growing a market for the product and achieving the central CSSR mission. The most important stakeholder was the customer because they are essential to the survival of the company, but also because owner-managers seek to change customers' awareness and behaviors as they relate to CSSR issues. Institutional constructs such as kitchen incubators enable entrepreneurs to start up but, along with limited local supply chains and costly and confusing regulations, they represent significant barriers to scale. The implication for social change within the local community is startup food incubators can use the findings to design models more conducive to scaling food SMEs that support local food production. This could benefit both local economic development and health outcomes.