Entrepreneurial enterprises take risks, innovate, and remain proactive in seeking business opportunities. For the past 30 years, entrepreneurial orientation theory has been the basis of exploring organizational behavior and has proven to be a reliable measure of what drives firm performance. Entrepreneurial firms remain adaptive by directing their internal and external capabilities to capture digital commerce and customer-linking opportunities. Thus, online marketing has gained in significance, suggesting that firms with the ability to leverage their digital marketing capabilities position themselves to gain a greater market advantage. In addition, the digital environment also offers unique opportunities for female-led firms with an entrepreneurial orientation. The possibility now exists for high levels of connectivity, adding value to the female owner’s ability to expand networks and increase social capital. Digitization of markets suggests new prospects for connectivity and performance gains not previously accessible. This is a quantitative survey explores the linkage between entrepreneurial orientation and firm performance when moderated by digital marketing capabilities and female-ownership behaviors, utilizing a database from the Carolina Small Business Development Fund, a state-wide community development financial institution offering small loans and grants to business owners in the state of North Carolina, and surveys collected from the digital platform LinkedIn.