Pamela Whitby talks team-building and philanthropy with the former co-founder of Kayak, who recently relaunched Lola, his latest business travel venture with an AI-human driven app

‘Why more women in computing is better for both women and computing’ was the title of an interesting LinkedIn post from Melinda Gates last month. It is also a subject close to EyeforTravel, and so it was heartening to hear from Paul English last week that women are integral to the team at Lola, his AI-human powered app that relaunched last week with a focus on business travel.

English, the former co-founder and CTO of Kayak, who is a Day 1 keynote speaker in Las Vegas next week, says: “I’ve been managing for about 25 years and I just know that teams are more functional if they are diverse, and gender is a huge part of that.”

...teams are more functional if they are diverse and gender is a huge part of that

He continues: “I can’t say women think one way and men think another because there are always exceptions, but I am interested in the dynamics between men and women when we're on a team together. I guess you will have noticed that men interrupt women more than women interrupt men, which is kind of awful. I watch for that kind of stuff in my meetings and try to call people on it.”

You only have to look at the Lola team page to see that he is not simply paying lip service to the issue of gender.

Among the women he has hired are Krista Pappas, the former Global Head of Business Development for Microsoft’s Bing Travel and customer service expert Stacey Scott, who leads his team of travel agents. “Stacey’s philosophy, which I fully embrace is to hire people first for phenomenal customer service skills and second for their travel expertise,” explains English.

Right now Lola has 15 human agents, which staff the app 24/7, with just a third coming from a background in travel.

Mixing it up

Although Lola is powered by technology, the Boston-born computer scientist “absolutely believes in power of the human” and having a diverse, mixed and entrepreneurial team. “We have people straight of school and people with 25 years experience. I look for diversity of all types of experience and for people from both small companies and larger companies.”

Most importantly, however, “every person at Lola needs to be an entrepreneur, no matter what their job is".

Even if they’ve come from a big company, English wants his people to be able to show that they done entrepreneurial things before, are “impatient and just want to get stuff done”.

Today, there are 50 in the Boston-based team, with 10% cherry-picked from Kayak. English was careful not to hire too many people from Kayak, because “it would be irritating to everybody else if they were constantly hearing ‘yeah we tried that at Kayak and it didn’t work’”.

Getting the best tech people counts too, and English has sought out the right people from companies like Facebook product manager Brendan Sullivan and Bryan Healey, a former software development manager at Amazon.

Healey, a data scientist and engineer joined Lola as Director of AI back in August 2016; at Amazon he was on a team of engineers working on the Echo/Alexa voice service, and has a background in Natural Language Understanding (NLU), which is used in both in text and voice. NLU experience is clearly useful for the Lola chat app, but although the team has developed a demo to release for Alexa, English is not yet sure about the future of voice. What he is clear about, however, is that text chat, which most users today seem to prefer, remains at the core of the app.

We are not going to try to trick you and pretend the bot is a human

Lola’s AI-fuelled chatbot technology is still work in progress but English is clear on one thing: “If it’s something obvious we want the computer to answer customers immediately rather than [wasting time] connecting to a human. But we will tell you it’s a bot. We are not going to try to trick you and pretend the bot is a human,” he stresses.

Transparency and philanthropy

At Lola transparency is important too. “I think Steve [Hafner] and I did a really good job at Kayak with that and I’m trying to do an equally good job at Lola,” says English. “I always tell people what’s on my mind. It’s important not to just to talk about the good stuff but to be open with people about what you are worried about.”

It’s important not to just to talk about the good stuff

Recently, for example, a board meeting when “pretty poorly” and he was “beaten up on some product issues”.

So, he took four pages of notes, to be shared with management first and then with the whole team to explain what the board is excited about and what they don’t like.

At Kayak everybody knows revenue and customer adoption numbers, although it’s too early for those to be made publicly available.

Another issue important to English is his philanthropic work and one of the biggest projects underway is in rural Haiti, which he first visited in 2003. Three years ago, English and one other foundation became one of the main funders of Summits Education, a school system that is investing in teacher training, while also building infrastructure.

He is also working with homeless populations in Boston and is involved in a major Martin Luther King memorial for the city.

So, it seems that not only is English investing in potent AI technology, he also seems to understand, in the words of MLK that “it is always the right time to do what is right”.

Join us in Las Vegas next week for EyeforTravel North America 2017 to hear more from Paul English and others travel tech movers and shakers.

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