Over the past 40 years, we have witnessed seismic shifts in advertising planning and buying processes. Due in no small part to the emergence of digital media, consumer choices have mushroomed, while advertisers understand much more about target audiences. Advertising activities have been drastically transformed by the possibilities that technology creates for targeting and measurement, automation of activities via programmatic advertising, and an overall computational approach in which algorithmic, data-driven decisions dominate. In this era, what does it mean to “do media planning” and to do it well? The present article argues for planning decisions to move away from simply purchasing exposure to instead focusing on fostering engagement through meaningful and sustained interactions with consumers. It provides an overview of the digital ecosystem that makes computational advertising possible, updates the notion of consumer engagement for this context, and reviews how measurement becomes more central to media planning decisions. Ethical and normative considerations and computational advertising as an adaptive learning system are discussed as crosscutting issues, followed by a proposed research agenda.