E-commerce has largely been a “Pull” model to date. Offline retailers have nailed discovery, delight, serendipity, and impulse purchases in person with greater success than online commerce sites. However, in an always-on, mobile-first world, companies like Groupon have the opportunity to push the frontier even further than offline retailers or comprehensive sites due to the fact that our smartphones are always with us. The challenge is to provide the right deals to the right user at the right time. That involves learning about the users and their locations, their personal preferences, and predicting which deals are likely to delight them, presenting diversity, discovery and engaging UX to gather user preferences and semantic graph approaches for user-deal matching. This presentation will give insight into how Groupon manages to grapple with these challenges via a data-driven system in order to delight and surprise customers.