Ineffective marketing strategies can negatively impact business competitive advantage. Small business owners who struggle to maintain a competitive advantage are at high risk of failure. Grounded in the technology acceptance model, the purpose of this multiple case study was to explore social media marketing strategies small business leaders in the wine industry use to promote brand awareness and maximize competitive advantage. The population comprised 5 small business leaders employed with 4 wineries in the wine industry in Michigan, who effectively used social media marketing strategies to promote brand awareness and maximize competitive advantage. Data were collected from semistructured interviews, company documents, and company social media platforms. Thematic analysis was used to analyze the data. Three themes emerged: customer engagement strategy, social media platform strategy, and targeted market strategy. The implications for positive social change include the potential for small business leaders in the wine industry to create jobs and support the economic development of the regional communities.