As the targeting technologies become ever more precise, political campaigns are running into the same challenge as consumer marketers: audiences that can be more finely segmented than the message. Without content that speaks directly to the values and concerns of a given voter, all that tech and targeting is squandered. Digital targeting finds voters. Are the campaigns really connecting with and engaging them? Targeted content is costly and time consuming. What does it take to make the messaging catch up to the technology? What have we learned from recent campaigns about the ROI on more customized content, how it can be made easier and cheaper?