startups (see Hopper, Spindle), everyone seems to have their own approach to achieving scale and/or finding new ways to slice data and content. “We’ve always been pushing the edge,” Conroy says. “We’re pushing on user-generated content, pushing on social, pushing on mobile. In order to be successful in social travel, you need to operate at scale, or it’s going to feel like an echo chamber. You get there, and there’s not much content there.”
Conroy also has thought a lot about the multiple-screen aspect of travel planning and sharing. One key theme is simplicity, he says, especially as the screen size shrinks. TripAdvisor didn’t have a mobile app for a long time, and its teams had to figure out how to “distill it all down, all that knowledge,” he says. “We’re a very data-driven company. We saw from our logs that people were accessing the site on phones. OK, so what are users using on their phones? What do we need to bring to that?”
The company built out its mobile presence accordingly over the past couple of years, and now it releases “dozens of new features every week,” Conroy says. “Some things work out really well, and some things don’t.”
One issue is that tablets and smartphones are two very different experiences. In terms of travel content, “the tablet is more akin to a desktop,” Conroy says, whereas “the phone has to support more, but be more focused on the in-market experience [while traveling].” And, of course, photos and maps can be bigger and potentially more interactive on tablets—and TripAdvisor has spent a lot of time working on that recently.
Conroy’s biggest lesson learned in his four years at the company? “I’ve gained newfound respect for how complex travel is, and how people travel around the globe,” he says. “The key is finding features that translate well across the globe. Everyone approaches travel differently. It’s a challenge figuring out how to roll out product globally from day one.”
Lastly, I asked Conroy about the company’s biggest challenge in 2013. “Hiring,” he says. “It’s a very competitive environment,” particularly in engineering and product design. He sums up the prototypical TripAdvisor employee as “moving fast, trying things, failing fast if needed, and making calculated bets.” As he emphasizes, “speed wins.”
Overall this fits pretty well with what CEO and co-founder Steve Kaufer told me a year ago about where the company is headed—particularly in international markets, and culturally. “We pay a lot of attention to how do we keep the entrepreneurial feel of the company going strong,” he told me at the time. “I never wanted to work at a big company. Our mission is to keep TripAdvisor a ‘small’ company.”
