AI, Chatbots, and Women: CEO Gillian Tans Strategy for the Future of Travel Technology

​“Within 3 years, over 50 percent of our customers will touch AI somewhere within booking” Gillian Tans, CEO of, predicted on the Main Stage of Startup Grind Global Conference 2018.  

Machine learning and Artificial Intelligence are not the only things Gillian has been working on. announced their Women in Tech Mentor Program at Startup Grind. This master program aims to give inspiration and mentorship for women on their path to careers in technology.

Booking aims to enrich the experience of booking travel by investing in AI, Chatbots, and Women in Tech.

Rising to CEO

Since starting at in 2002, Gillian has risen to CEO in 2016 and now ranks 37th on the Most Powerful International Women List according to Forbes. is owned by Priceline Group (PCLN), who will change to Booking Holdings (BKNG) on February 27th, This reflects’s importance to the umbrella company since their acquisition in 2005. offers hotels in 228 countries and employs over 15,000 people in 198 offices worldwide.

AI & Machine Learning at uses machine learning to find what their customers search for on Google. From this information they can recommend relevant destinations, route customer service calls in their call centers, and design updates for their website.

Gillian explains that, “every customer today touches machine learning already, anywhere on our product.” However Gillian has realized that this is not enough. “Deciding on which property you are going to book in Rome where you have 8,000 choices for that specific customer is extremely difficult.” As a result, they are employing chatbots to help solve the problem.

Chatbots - Booking’s New Travel Assistant

In September, purchased Evature, a Tel-Aviv based AI company that created an Expert Virtual Agent (EVA) chatbot to talk the customer through the entire travel booking process.

Gillian Tans went on to say that 30 percent of English speaking customers already use their Booking Assistant.  It uses natural language processing (NLP) technology along with AI and machine learning to offer immediate customer service feedback.  

Gillian explains the Booking Assistant experience, “You type: ‘I want to have a hotel in Paris,’ and basically this bot will take you through the whole search process to eventually get the property booked.’s Women in Tech Mentoring Program has a pledged STEM scholarship grant for Women in Tech with the University of Oxford and TU Delft, totaling €500,000. Booking hosted an all women hackathon in July and will host the Inaugural Technology Playmaker Awards in London on March 8th. This special inaugural will be to commemorate the achievements of Women in Tech.  

Gillian, along with the other speakers at Startup Grind, sat one-on-one with women attending the conference for 30 minute sessions, as a part of Booking’s Women in Tech Mentor Program.

The Future of The Online Travel Industry

When addressing the future of the industry, Gillian reports, “we see overall travel is increasing and I think it will continue to do so.” Gillian highlights recent competition from Airbnb as she announces to the audience: “we now offer experiences in 30 cities to customers.”  

Gillian also explains that the apartment and home property rentals were a big focus for Booking, and she claims, “Airbnb is very successful in the home and apartments sector, but in many countries in Europe, Booking is already leading in this space.” is looking to gain market share in the United States, where it has “much to gain in the home and apartments sector.”

Regulatory Landscape Creates Risk for Booking

For to list apartments in a new city “it is important that the regulatory landscape is clear. That’s something that we help cities with as well.” Since they are a publicly traded company, protecting investors from regulatory risk is very important.  

On the other hand, Airbnb is privately owned and seems to be asking for forgiveness (and support from customers), rather than permission at City Hall Meetings around the world. This could significantly limit Booking’s market share in the home and apartment rental space in the years to come.

Opportunities for Innovation in Travel

Gillian told the audience, “there are many areas where friction for customers can be solved” within the travel industry.  Recently, her team is focusing on the question: “How can we offer transportation to customers to the property? We think more and more about how we can help customers once they are at their destination.”

Again, Gillian noted “family and business travel” as possible areas we might see innovation in the travel industry. To highlight the many ways entrepreneurs can get into the travel industry, she gave a shout out to a woman she mentored: “Many homes and apartments don’t have a place to store luggage and she solved that problem, which I think is amazing.”


The near future of the travel industry is a race for apartment and home rental market share and for the best and most personalized customer booking experience possible.  With their dominant share of the travel booking data market and recent acquisition of Evature, it’s only a matter of time before Booking turns into your personal travel assistant.  

Booking and Airbnb will try to maneuver the regulatory landscape of the global apartment and home rental market, however these company’s have proven that with innovation there is certainly still ample opportunities that are presenting themselves in the travel industry.