This study examines how the relationship between entrepreneurial orientation and firm growth is shaped by learning orientation in technologically sophisticated environments. We draw upon an information processing perspective that emphasizes alignment between information processing demands and support mechanisms. Using data from 116 small to medium‐sized enterprises in the Netherlands, we observe that the ability of entrepreneurial orientation to drive firm growth greatly depends on the joint consideration of technological sophistication and learning orientation. Our findings contribute to a better understanding of how configurations of strategic orientations and environmental considerations work in concert to influence the efficacy of organizational entrepreneurial efforts dramatically.