Skift Global Forum: HotelTonight’s Founder on the Challenges of Curation

Travelers were once wowed by the ability to search through thousands of flight and hotel options to find the best selection.

Today, they’re looking for the best option without hours of hard work — and are expecting their favorite brands to deliver that option based on their previous bookings.

HotelTonight is working to deliver that experience to its mobile-first customer base and learning important lessons about the challenges and benefits of curation along the way.

HotelTonight founder and CEO Sam Shank will speak about the future of curation at the Skift Global Forum on The Future of Travel on October 9 in New York City. He talks about the future of curation and HotelTonight in the exclusive interview below.

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Skift: What does curation look like in 5 to 10 years?

Sam Shank: The way we think about curation at HotelTonight is that it should feel like recommendations from the coolest person at the cocktail party you are at or recommendations from your most in-the-know friend. We’re getting there, but we need to learn a lot more about the customer and their needs and be able to utilize that information to connect the dots to make even better decisions. It should feel hand-picked, hand-crafted and not the result of using a bunch of filters.

Skift: What’s the balance between curation being hand-picked by a human versus calculated by an algorithm?

Shank: I think it’s a combination of both. To scale curation, to make it truly personalized and individual, responsive and real-time, there has to be an automated level to it. But there also needs to be a human element because it is very hard to tell a machine what cool means or what cozy means. Those are concepts that humans are better than machines at defining and refining.

Skift: Is curation only possible in hospitality? Or can it be brought to transportation?

Shank: I think in the first phase of travel commerce it was about connectivity and providing access to every possible option. That was great and brought you an amazing amount of selection, but with that you needed ways to filter and refine that selection.

On a mobile device, we don’t have screen real estate to make that a satisfactory experience and people are also busier. The idea of having to go through 2,000 hotels in Rome and refine and hone those down to the right hotel for you, that doesn’t seem magical on a mobile device. It seems like work.

I think that’s why curation is such an important concept for mobile commerce, because of the limited attention span of people as well as the screen real estate. People just want to see the best things or the right things for them.

With car rentals and flights, those are more commodity options so curation isn’t about showing the hippest flight — it’s about showing me the flight that’s right for me, that’s the best option for my needs. My needs are different, sometimes I’m optimizing for fewer connections or lower price or takeoff time.

That’s different based on the context of when I’m flying so understanding that context is terribly important for curation to work.

Skift: How is HotelTonight working to improve curation?

Shank: We’ve been thinking about and working on it for the three years since we launched. It’s manifested in different ways. I’ve talked about this year being the year of context and really understanding the needs of a consumer and how those needs change from time to time, location to location, and moment to moment so we can bring them the best results to save them time and to increase their loyalty.

The challenges with curation and personalization and context awareness are around the presentation layer of that information. How do you do it a way that customers understand you’re adding value and they understand what they’re seeing and why?

The other challenge is on the backend and being able to massively scale personalized results that are different for every customer that comes to HotelTonight. That’s massively challenging from a technical perspective, to be able to deliver those results in a scalable, reliable way.

Skift: How do you view the competitive landscape and rising number of HotelTonight-like apps?

Sam Shank: Launching is the easy part. The hard part is really operating the business. It’s very hard having great deals that are better than anything else in the market every day. It’s very hard taking care of customers and it’s very hard showing value to hotels. We have a really nice flywheel going where we bring value to hotels and then they get excited about working with HotelTonight.

We haven’t seen any one come close to that flywheel or brand awareness and loyalty and I think it’s going to be hard for anyone else to do. The market is different than when we launched.

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