Research on news organizations’ approach to digital media in the 1990s and 2000s generally found that most organizations adopted a defensive approach. Since then, both digital media and news organizations have continued to develop, and we cannot simply assume that the approach remains the same. In this paper, we analyse how a purposive sample of 19 news organizations across three different countries approach online video news—chosen as a paradigmatic example of the current move towards a more mobile, platform-dominated, and video-enabled digital media environment. On the basis of semi-structured interviews with senior people across the sample, we argue that most news organizations today adopt a far more enterprising approach to digital media than that found in the 1990s and 2000s, and invest in what they see as promising opportunities in an uncertain environment. We find that decisions to invest in online video news are shaped primarily by a perception of what audiences want, what platforms like Facebook and Google/YouTube prioritize, and the prospect of lucrative video advertising. Editorial considerations seem marginal. The enterprising approach and the considerations behind it are broadly similar across the organizations and countries covered, with exceptions (some broadcasters and German news organizations).