Extant research has shown that entrepreneurial orientation (EO) is positively associated with firm performance, but several contingencies affect the strength of this relationship. This article uses insights from the resource-based view and upper echelons perspective to introduce top management’s transformational leadership behaviors as moderators in the EO–performance relationship. The theoretically derived model is tested using survey data obtained from 790 small- and medium-sized firms in six countries. Findings indicate that, regardless of national setting, four transformational behaviors—articulating a vision, providing an appropriate model, having high performance expectations, and showing supportive leader behavior—positively affect the relationship between EO and firm performance. Further, the performance consequences of EO are greater when top management adheres to a configuration characterized by the highest possible levels of transformational behaviors. Implications and directions for future research are discussed.