This article focuses on the complexities of managing multi-platform strategies in the complex and highly dynamic environments of contemporary media markets. Based on a comparative case study of two Nordic media organizations, the article identifies and articulates two sets of practices through which strategy is managed in the continuously changing print and online environments. While the practices that guide strategy development of print publishing tend to be content driven, brand constrained, commercially steered, and top-down monitored, strategizing for online platforms tends to be more technology driven, brand inspired, interactive, and entrepreneurial. For multi-platform media organizations this type of situation is challenging because the incremental and radical innovations that they pursue are platform specific, instead of aiming at exploitation and exploration on both platforms. To succeed in the market, the article argues, multi-platform media organizations need to develop strategies and organizational practices that allow them to be truly ambidextrous—to pursue both incremental and radical change—on all platforms