Entrepreneurial orientation (EO) refers to the corporate tendencies that enable a firm to adopt an entrepreneurial posture toward new business opportunities (Lumpkin & Dess, 1996). EO is defined as “the simultaneous exhibition of innovativeness, proactiveness, and risk taking” (Stam & Elfring, 2008: 98). As knowledge in the area of EO has expanded, increased attention is being paid to the contextual factors that may change the degree or nature of the EO-performance connection. From an upper echelons perspective, top management’s characteristics play a major role in converting EO into superior performance (Covin & Slevin, 1991). We examine whether the effect of EO on firm performance is contingent upon the power vested in the chief executive. Therefore, the present study is located at the intersection of entrepreneurship and upper echelon (Engelen, Gupta, Strenger, & Brettel, 2013), a fertile area of inquiry that has begun to attract the attention of researchers and scholars (Ling, Simsek, & Lubatkin, 2008; Simsek, Heavey, & Veiga, 2010).