Contrary to conventional wisdom, this study demonstrates that technological laggards and not industry front-runners are most likely to experience high rates of technological advancement in strategic alliances. We further suggest that imitation and not innovation is the primary source of such advancement, based on the fact that technological progress by laggards is most visible in industries that lack strong appropriability regimes. Finally, we present empirical evidence suggesting that lagging established corporations prefer to imitate from startups and not from fellow incumbents. These results are derived from a careful analysis of a longitudinal sample of over 150 incumbents with varying degrees of technological prowess that engage in partnerships with both startups and fellow incumbents across a wide representation of industries. Our chapter contributes to technological innovation, strategic alliance, entrepreneurship and imitation literatures, and provides non-trivial implications for startups.