Marketplace matching is about matching both sides of the ecosystem, in Airbnb's case we're matching guests with hosts and understanding their unique preferences. Airbnb's inventory is extremely diverse, and different trip planners come to the platform with different goals in mind. In 2015, the Search team launched several experiments to help trip planners understand our inventory, narrow in on a subset of results relevant to them and build confidence in their booking decision. In this talk, we'll discuss these experiments and what we've learned from them, successes we've had with Machine Learning and some directions for future work.