There is considerable agreement that firms behaving entrepreneurially perform better than more conservative firms (Covin & Lumpkin, 2011). To this end, a firm’s entrepreneurial orientation (EO)—that is, its overall strategic posture to be innovative, proactive, and risk taking—takes on instrumental importance (George & Marino, 2011). Several studies establish boundary conditions for when it favors firms to embrace entrepreneurial strategies and when it may not. This study conducts a longitudinal analysis of the EO-performance relationship over an extended period of time, and explores the role of two potential moderators- competitive intensity and demand volatility- in properly and successfully aligning EO with the industry environment to derive positive benefits from enacting an entrepreneurial strategic posture.