WaySavvy, With Expedia Partnership, Joins New Wave of Online Travel Sites

A collaboration between New England and Northwest techies is aiming to radically improve the way people book flights and hotels on the Web. If all goes well, it will become part of a broader movement of tech companies looking to reshape the online travel landscape.

I’m not talking about the alliance between Microsoft’s Bing Travel and Connecticut-based Kayak, announced on Friday (though that’s important too). I’m talking about a small startup based in Boston and Seattle called WaySavvy.

Late last week, the six-person company signed a key partnership with Bellevue, WA-based Expedia (NASDAQ: EXPE) that gives it access to a “global distribution system” that books and sells airline tickets and hotel stays. That also means the startup is connected to a large swath of itinerary and pricing data. In short, WaySavvy is now in business—more specifically, in beta trials with its early customers.

Its main goal? “We make it incredibly easy to book a trip,” says WaySavvy founder and CEO Michael Raybman. He has been working full-time on the bootstrapped startup for just over a year, collaborating with his chief technology officer in the Seattle area (whose day job is at Microsoft though he’s been working 50 hours a week on WaySavvy).

What’s interesting here is not so much WaySavvy’s specific technology or product just yet (more on that in a minute). It’s that consumers’ frustration with booking trips online has given birth to a new generation of online travel startups, many of which are focused on making the booking process faster, more efficient, and more informative. Xconomy has profiled Hipmunk (and its new hotel search system), InsideTrip, and Raveable on the West Coast, but there’s also Wanderfly, Yapta, YourTour, Goplanet, TravelPost, and others, in addition to WaySavvy.

Over the years, travel companies have tended to come in waves—first led by firms like Expedia and Travelocity, then Orbitz and Hotwire, and then Kayak and Farecast (now Bing Travel). Whoever survives from the current crop of upstarts should be well-positioned to carry the torch.

Raybman’s interest in building a travel startup comes in part from serving as the “de facto travel agent” for his extended family, he says. He’s a recent Brandeis University graduate who previously worked on healthcare modeling software at Brigham and Women’s Hospital in Boston.

He gave me a quick demo of WaySavvy last week. The site is simple: you tell it where you want to go and when, and it filters airfare and hotel results by cheapest, swankiest, and best bang for the buck. Its software takes into account the timing, price, and comfort of flights, length of layovers, distance between airport and hotel, and other factors, and then it suggests an ideal itinerary for you (which you can accept or change). The goal is for people to go “from search to booking in a couple of minutes” instead of visiting multiple sites or paging through endless listings, Raybman says.

Of course, the startup’s success will depend on how well its algorithms deliver choices that people want. The plan is to personalize each consumer’s search experience based on his or her preferences, Raybman says. Another big challenge is getting enough people to use the site. For this, the company plans to get its name out there through the media, word of mouth, paid search, and partnerships with travel sites and other organizations that might want a piece of a booking system. And it will be looking to form direct partnerships with hotels and airlines to sell itineraries.

I pressed Raybman a little on how WaySavvy will separate itself from such a crowded field. “We are the simplest and fastest way to get a great deal and a great trip. We do the heavy lifting for you,” he says. “Even if Hipmunk and Wanderfly do extremely well, there will be enough of a pie for everyone. There is big potential here if we can break the behavior patterns of [people] looking at 1,000 choices before [booking a trip].”

As for the big entrenched players, Raybman sees a “big decrease in the importance of meta-search because price parity is going to get to 100 percent,” he says. That means firms like Kayak might look more outside of hotels and airlines, or move into direct bookings, or use a bidding model like Hotwire or Priceline. Meanwhile, he predicts Microsoft will make another acquisition or two, and Google will support search queries like “what is a good getaway from Boston this summer?” but probably won’t get into booking trips.

That reminded me that Google is still in the process of acquiring Cambridge, MA-based ITA Software—whose technology powers the flight search and pricing engines for airlines and travel sites—against the wishes of Microsoft, Kayak, Expedia, and others. Raybman had high praise for ITA, saying it is “the best-positioned company to not go away, and to be the technology provider that works well in the new ecosystem with suppliers and airlines.”

Lastly, I had to point out that online technology has its limits: it won’t ease some of the biggest air travel frustrations, like screaming babies, long security lines, and rising fuel prices.

“Unfortunately, we’re not doing anything about that just yet,” he says.

Gregory T. Huang is Xconomy's Deputy Editor, National IT Editor, and Editor of Xconomy Boston. E-mail him at gthuang [at] xconomy.com. Follow @gthuang

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