Conventional wisdom suggests that early entry into a market with an innovation confers enduring competitive advantage upon a firm. Empirical evidence to this effect is mixed. Despite claims that “earlier is better,” results on early-mover advantages are inconsistent. Drawing on two in-depth interviews with senior technology industry executives (former CEOs/CMOs with multi-decade experience in printing, telecom, networking, cybersecurity, and collaborative technologies), we explore conditions under which entry timing (early vs. late movers) leads to sustainable competitive advantage. The executive interviews suggest that timing is a necessary but not sufficient condition, resulting advantages hinge on the contextual effects of ecosystem economics, innovation characteristics, and organizational “will and skill,” among other things.