In the first of two write ups from this week’s interview with the former founder of Kayak, Pamela Whitby gets an update on his latest entrepreneurial endeavour – a super-powered AI-human chat app for business travel

Brilliant, intense, generous and erratic is how the New York Times described Paul English in an article published in October 2016. But in an interview this week with the former CTO and cofounder of Kayak, who is now hoping to conquer business travel with chat app Lola, he seems a modest, honest, if determined, kind of bloke.

To be fair, however, the New York Times was reviewing English’s biography – A Truck Full of Money – by the Pulitzer prize-winning author Tracy Kidder. This week’s interview for EyeforTravel, on the other hand, was perhaps a little more mundane – to hear what English might touch on in his speaking slot at EyeforTravel North America 2017, which is being held in Las Vegas on October 19-20.

Before getting down to talking about English’s latest venture at Lola, we agreed that if this going to be an important gathering of the travel industry then, in spite of the senseless shooting in Las Vegas, the show should go on – as we reported on Wednesday in EyeforTravel supports industry in a show of solidarity to Las Vegas.

With English, who exited Kayak after selling the business to Priceline for $1.8 billion in 2012, counting himself among the travel industry great and good attending the summit, let’s just say it’s going to be important gathering!

Lola where are you now?

From the recent book by Kidder to countless articles documenting English’s various endeavors and escapades – including a stint as an Uber driver – since selling Kayak to Priceline for $1.8bn in 2012, there has been plenty written about the Boston-born entrepreneur.

But what has been happening at Lola, which was touted as one of travel tech’s hottest start-ups in 2015/16?

Well, yes, the now 50-strong Boston-based team of travel agents and data scientists has been focused on building out a travel chat app that is super-powered, both by artificial intelligence and humans.

But since interviewing Lola VP Krista Pappas earlier in the year, there has been a clear pivot to business travel. What surprised English, he says, was that it soon became clear that the majority of Lola users – about two-thirds – were business travellers.

“This caught me off guard because at Kayak we never built any specific business features, and so we [also] didn’t at Lola. Yet, at Kayak just 25% of users were business road warriors,” he says.

This led English to try and fully understand why Lola users were predominantly business travellers. So, he hired Paul Sullivan, a former product-marketing manager at Facebook, to help figure this out. A year on and Sullivan is now VP of product at Lola and the focus is 100% on business travel (notwithstanding that they do understand that some business travellers want to combine work with leisure!).

In getting to this point, the team identified the ten Boston companies using the app most, and met with both users and managers to get to understand their needs – what tools they were using, what they liked and disliked most about Lola, why it needed to be different from leisure and so on.

In addition, focus groups were set up with regular road warriors – those travelling as much as 20 times a year – who had never used Lola before.

In doing so, English says three things stood out. 

1.  Personalisation: Like the power travelling character of George Clooney in the film Up in the Air, road warriors class themselves as super efficient, but they have a number of specific demands. This varies too by age. For younger road warriors, it’s all about excitement and adventure. They like to spend an extra day or two in the destination, mixing business with leisure. Older road warriors, in their 40s, just want to get home for the kids’ soccer game or whatever else is going on in family life.

One of the biggest insights came from the older road warriors, who said they yearned for the good old days when the flesh-and-blood administrative assistant (AA) booked your travel and just knew exactly what you wanted – from what airline you wanted to fly, to which hotel you wanted to stay at and where you wanted to eat.

“I feel a bit guilty that I’m partially responsible for this [demise of the AA],” says English.

It was, after all, the rise of sites like Kayak that resulted in road warriors increasingly being forced by their companies to book their own travel. And by English’s own admission, Kayak was doing nothing to service this segment.

So what is Lola going to do about it?

We’ve put a lot energy into AI about how personalisation works and we think we have come up with something that is quite different

“We’ve put a lot energy into AI about how personalisation works and we think we have come up with something that is quite different,” says English.

Users, as a starting point, are asked to tell Lola about a few hotels they have stayed at. Then the AI gets to work extracting information about historic price range, affiliated brands, its size, the last renovation and more. Lola, says English, has “scraped millions of reviews across dozens of sites” to see what adjectives are used to describe hotels. And so it goes on.

It is from this, huge pool of data, and hugely relevant information that it is able to deliver a map showing hotels that a road warrior may actually like, and usually at a better price.

“Our AI is literally showing you the best hotels that match your criteria instead of the hotels that make the OTA the most of money,” he says. 

2.  Direct bookings: What team Lola also understands is that the road warrior is sophisticated. They want their loyalty points and they want to be able to spend them on the airline or at hotel of their choice such as on a family trip. But when you book with the OTAs you don’t get those points. “So we’ve built a Sabre integration because, as you know, with the GDSs when you book the national chains its same as booking direct – get you 100% of those rewards points,” he explains.

3. Service: Finally, and arguably most importantly, is the notion of providing a service, which is particularly useful when you are on the road. You want someone to figure out how to get home quickly when the flight’s delayed, ideally with no cancellation fees. You may want someone to contact the hotel to say you’d like to check in early to have a shower before the meeting and so on. On the road, Lola’s team of agents – and yes they are humans – will take care of things for you, and deliver a “seamless experience that is deeply integrated into the app”. Importantly though, if users want to speak via telephone or email (and they are working on a demo for Alexa), this is possible too. However, English says most if their users today seem to prefer messaging.

With just about all the $45-million raised so far sitting in the bank and ready to take plans forward, English says Lola is fully funded for at least two years.

“We want to do a really good job with business travel, because no business is creating really great features for business,” he says.

Forget gimmicky kickbacks like Amazon gift cards, we are talking flight algorithms that simply aren’t going to show an unwanted layover that could make delay a meeting.

And like we said, English seems pretty determined.

Next week more from Paul English on voice search, hiring the best, being transparent and his philanthropic endeavours.

If you’d like to hear him speak, why not stand in solidarity with the travel industry and join us in Las Vegas to hear more on October 20.

*Note: 20% of all future tickets sales to the event will be donated to the victims and their families*