Rob Ransom of Booking Holdings On The Future of Travel in The Post Covid World
Preserving the planet isn’t a job for just one business or one industry. It is an incredibly complex space. While we’re making strides in our own operations and to surface sustainability-related practices and information to customers on our platforms, there are small steps each and every one of us can take in our own day or on our next trip — from purchasing carbon offsets for your next flight to bringing a canvas bag with you when you head out on your next grocery trip. Collectively, that can make a meaningful impact.
As part of my series about developments in the travel industry over the next five years, I had the pleasure of interviewing Rob Ransom, Senior Vice President and Chief Strategy Officer at Booking Holdings, the world’s leading online travel company, with brands including Booking.com, KAYAK, OpenTable, Priceline and Agoda.
As Chief Strategy Officer at Booking Holdings, Rob is responsible for overall company strategy, corporate business development, and the company’s global sustainability strategy and programs. Rob has been instrumental in defining the company’s global strategy, accelerating into new verticals and supporting continued company growth through identifying new market opportunities, strategic partnerships and investment opportunities across the travel technology ecosystem. He has also been a member of the Booking.com Leadership Team since 2014, prior to which, Rob spent over a decade in digital media, software and product marketing following his time as a management consultant at McKinsey & Company.
Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?
Well, I have never been that person who from the age of eight knew what they wanted to do when they grew up… Early in my career I was more curious than focused. So a lot of key steps in my career were somewhat circumstantial, resulting from the opportunities that were interesting and available at the same time that I was actually open to new opportunities. Experience has shown me that opportunities rarely show up in predictable ways, and that staying connected with people you know and who know you is a great way to surface opportunities. For example, I joined Booking.com in Amsterdam from a role as CEO of a small digital content company not in the travel industry and based in British Columbia — so I changed industry, company size, role, and even continent all at once. But such a move makes a bit more sense when I explain that I was hired by my former manager at McKinsey, Booking.com was launching a B2B initiative and looking for someone with a B2B SaaS background to lead it, and my wife and I had been discussing how to get back to Europe after a brief stint there in the 90s — so the stars all lined up at the right moment then.
Can you share the most interesting story that happened to you since you started your career?
One of the recurring themes I have focused on in the last 20 years or so of my career is the power of technology to help medium and small businesses be more successful. This first hit home for me when I was a product manager at a company providing lead generation and CRM tools for real estate agents and brokers. As a product manager I spent a lot of energy focusing on the software and the go-to-market plan and the business model, but I remember at one of our first customer events I gained an entirely different perspective. I was speaking to a woman who explained how much she loved our product. But she loved our product because it had completely changed the trajectory of her real estate career from struggling to earning a fantastic steady income, to changing her relationship with her colleagues and, as she quickly explained, giving her confidence that she had never felt before. Now of course she certainly had all the capacity for success within her, but somehow our little product had helped unlock this potential. This made me realize that working with entrepreneurs and small business people who have the motivation and hustle but maybe not the tools they need can be really rewarding, sometimes much more than landing an enterprise deal with a Fortune 100 company. I have seen this pattern repeated across a number of industries including hospitality and while the technology continues to evolve, the potential to help people and businesses be successful remains.
Can you share a story about the funniest / light-hearted mistake you made when you were first starting? Can you tell us what lesson you learned from that?
The first project I ever did at McKinsey was for a big global energy firm, and my mistake was simply assuming that I knew anything! In the kickoff meeting with the client team, I remember going around the table for introductions, and was tongue-tied when I realized that most of the team members had been working at the company longer than I had been alive! It didn’t seem to be that compelling to share that I was fresh out of university and had been a consultant for 2 months. But the project ended up being successful, and it was a great lesson for me early in my career because I had to learn quickly how to build relationships and credibility where I had none. Again and again throughout my career, I have leaned on this lesson to understand what challenges people are facing, really listening and connecting with them as people, and usually finding ways that you can help.
Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”? Can you share a story about that?
Finding what brings you energy, in your work life and outside of it, is key here. In my work life, I have learned over time that on days when I am in the office with my team, having dialogue about how to chase down a new opportunity, innovation or partnership to help deliver even more value for our customers, I come away from the day energized. I really enjoy team-based work, and seek it out, even if we are in different locations. The other thing is just ensuring teams have real clarity and focus. I have found burnout and frustration doesn’t necessarily come from working hard. It is more of a risk when people feel their work isn’t valued, or the purpose isn’t clear. This drives frustration and frustration is exhausting. So it’s really worth the extra effort to bring clarity wherever possible.
Outside the office is also important, everyone needs to have those activities that give them energy and a different mental focus from the intensity of work. For me I really try to do some exercise every day, usually running, going to the gym or playing tennis. Time with family and friends not talking about work is also restorative. I have three kids so just keeping up with them and their busy lives definitely gets my mind away from the office.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?
There are many people who have helped and supported me along the way, but two come to mind quickly. The first is my high school English teacher, Tom Doelger. An incredible and engaging teacher, he more than any other person taught me how to write, taught me grammar, how to read and to understand both what is and what isn’t on the page… basic tools that I have literally used every day since. But more important is that he had incredibly high standards for himself and high expectations for his students. He was warm and supportive, but didn’t let that translate to lowered standards or disregard for the learning at hand. He had a really amazing impact on me as a thinker and communicator from early in my life.
The second is my wife Katy — her belief in me and support, while also pushing me to be better, has often been stronger than my own and for that I am forever grateful. I can only wish that everyone has someone in their life like Katy has been there for me.
Thank you for that. Let’s jump to the core of our discussion. Can you share with our readers about the innovations that you are bringing to the travel and hospitality industries?
Our mission is to make it easier for everyone to experience the world. We see technology and innovation as central to that, and everything we do is with the aim of making travel easier, more personalized and more responsive to the customer, whether that’s a traveler or one of our travel provider partners. Our brands are constantly creating and improving products and services that do exactly that. Think about 20 years ago when the idea of booking an accommodation or flight online was totally novel. Booking.com, Priceline, KAYAK and Agoda helped make that commonplace, bringing new customers to businesses all over the world — all through technology. OpenTable pioneered the same for restaurant reservations and technology.
At every step of the way, we’ve adapted our technology to stay ahead of customer expectations and innovate to meet their needs. Now, with the advent of AI — including generative AI — and strides in fintech, we’re accelerating into the future of travel, further connecting each step of the traveler and partner journey on our platforms to bring that easy, personalized, responsive experience to life.
Which “pain point” are you trying to address by introducing this innovation? How do you envision that this might disrupt the status quo?
The complex, fragmented, and sometimes frustrating parts of the travel experience are what keep our teams chasing our mission and a better future for travel. Take something as simple as your flight being delayed. We’re striving for a world where you don’t need to ping the rental car company, the bed and breakfast, your tour guide and the restaurant you have a reservation at for dinner to let them know you’re going to be late. What if that all just happened automatically with the power of technology? We’re not far off from a reality wherein technology — including AI, generative AI and machine learning — can actually anticipate and solve the needs of a customer as the unexpected happens to create that fully seamless experience, from searching and planning to the in-trip experience to the return home.
As you know, COVID19 changed the world as we know it. Can you share some examples of how travel and hospitality companies will be adjusting over the next five years to the new ways that consumers will prefer to travel?
To say the pandemic was a trying time for the travel industry would be an understatement, but the resilience of travel has proven itself over and over again. The predominant notion I get when I think about the next five years is just that we know that when people can travel, they will. And travel and hospitality companies are doing everything they can to welcome those travelers.
When it comes to how consumer preferences have changed, what we’ve actually seen is that the pandemic accelerated existing trends including turning to more types of accommodation — such as homes and apartments — as well as demand for more flexible options when things don’t go exactly as planned. These have been priorities and hallmarks of our products and services, even prior to the pandemic, so we continue to lean into this to meet traveler needs and personalize their experiences on our platforms even further.
You are a “travel insider”. How would you describe your “perfect vacation experience”?
For me, the perfect vacation is going with my family to a beautiful resort near the sea, in a place with easy access to tennis courts, and the opportunity to eat all my meals outside in the open air while sitting and chatting with my family and friends. I also like to have easy access to trusted “insider” recommendations from people with similar preferences to me in order to know which activities to do, which restaurants to book, which trails to hike — this can make new places so much more enjoyable. Despite having many opportunities to visit beautiful places over the years, it’s also exciting to me that there are so many more that fit this bill that I haven’t been to yet and hopefully get to explore in the future.
Can you share with our readers how you have used your success to bring goodness to the world?
We know that the success we’ve had as one of the world’s leading online travel companies comes with a responsibility to ensure that there is always a world worth experiencing. We have a unique opportunity to lead and support positive changes throughout our industry and meet the growing demand for more sustainable travel choices. Our work in this area is rooted in commitments to operate our business more sustainably, to make it easier for travelers to make more sustainable travel choices and to catalyze sustainable travel growth through external collaboration.
Preserving the planet isn’t a job for just one business or one industry. It is an incredibly complex space. While we’re making strides in our own operations and to surface sustainability-related practices and information to customers on our platforms, there are small steps each and every one of us can take in our own day or on our next trip — from purchasing carbon offsets for your next flight to bringing a canvas bag with you when you head out on your next grocery trip. Collectively, that can make a meaningful impact.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.
I truly believe people traveling is a force for good in the world — it promotes understanding and communication and opens new worlds to so many, so I’ve often tried to think of clever ways to leverage the sheer size and power of the travel industry to truly make the world a better place for everyone to experience. One idea I’ve tossed around is if we can simply get everyone who travels to add $1 to the cost of their trip to be donated to a fund dedicated to making travel as accessible and sustainable as possible. Imagine getting travel suppliers to also dedicate $1 per trip — you would relatively quickly have hundreds of millions each year to invest in projects and programs from which people all across the globe would benefit. If we could create such a funding source, I know there are many brilliant people with ideas to make good use of those resources. I would love to see that happen…
How can our readers follow you on social media?
You can find me on LinkedIn, or follow Booking Holdings on LinkedIn and X.
This was very inspiring. Thank you so much for joining us!
