While there is growing interest in exploring strategic orientations, their interaction, and impact on firm performance, most research has been conducted within stable economic environments. Taking into consideration economic instability, it is timely to develop a more nuanced understanding of how economic crises may affect key strategic orientation prescriptions. In this research, we examine entrepreneurial and market orientations as means through which firms may operate within an economic crisis to seize available opportunities. Additionally, we consider how increasing financial resource availability during macro-economic constraint may affect these relationships. Based on a rare, and robust national random sample of 612 Russian small to medium-sized enterprises (SMEs) collected during a recent period of economic crisis in 2015–2016, our results reveal a positive effect of entrepreneurial orientation and a non-significant effect of market orientation. Moreover, we demonstrate how financial resource availability in concert with firms’ strategic orientations yields distinctly more, and less, productive configurations.