Vienna Insurance Group (VIG) and UNIQA are two insurers headquartered in Vienna which expanded successfully to Central and Eastern Europe in the last 30 years. While similar in their internationalization motives and "going east" strategy, they followed different brand strategies. VIG bets on a multi-brand strategy, UNIQA on a single-brand strategy. Both insurers are convinced that they pursue the right strategy. What are the reasons for choosing the respective brand strategy? What challenges have they faced in managing their brands? How does the increasing digitalization affect the brand strategies?