James Lemon: Envisioning a future of fully frictionless payments while traveling

James Lemon

Travel’s really different, and that makes it in the kind of legacy of the payments industry. That makes it quite high risk because you might be handing over thousands of dollars, euros, or pounds, you know, days, weeks, even months, sometimes years before you actually can kind of consume the trip, if you like.

Sebastien Leitner

Hi there. My name is Sebastien Leitner. Welcome to the podcast. I have to talk to you about James Lemon from Stripe. He’s the head of travel at Stripe, and he’s such a fun guy. I had a great conversation with him. He’s the kind of guy who you want to have a beer with, first of all. He’s a really nice chap, but he’s also super experienced, brings a lot of wealth of information and knowledge and experience from hospitality. I think he started his career in hotels.

And then on top of that, he’s been able to establish over the years a huge network of industry influencers. He’s very well connected, and he’s a continuous learner, really smart guy, really inspiring conversation, and some great insights around what are some friction points in payments and how to overcome them.

Welcome. I’m super excited to be joined here today by James Lemon. He’s the global lead of travel, transport, and leisure. It’s quite the mouthful. James, welcome.

James Lemon

Thanks, Seb. Good to be here.

Sebastien Leitner

My opening question has to do with the name of this podcast, which is the turndown, of course. What is keeping you up at night these days, James, as a global lead of travel, transport, and leisure at Stripe?

James Lemon

Yeah. So generally, I sleep pretty well, I have to say. Post pandemic, things feel a little bit more normal for our industry and the things we’re all trying to get done in our day jobs and our home lives perhaps. I think if I was to focus straight in on where there are still challenges, I’m genuinely concerned about the hospitality and the wider industry’s ability to retain great people.

I think it definitely came about during the pandemic that whether you’re on the frontline, whether you’re in ops, whether you’re in HQ, whether you’re in tech, hospitality is not always the most kind of vibrant first choice career. And I see lots of people now trying to work on that, and I think that’s absolutely the right thing to do. But I think we’ve still got a way to go. If we wanna deliver the amazing experiences we think the industry deserves, if we wanna be the kind of innovators we want, there’s a group of us, you’re probably one, I’m probably one, that we’re spending our lives in this industry. We absolutely love it to bits.

But I do worry that the next generation leaders, the next generation of teams in our hotels and running our businesses may choose other things to do with their time as new career options become available. So that’s probably the number one thing.

Sebastien Leitner

And you’re a great example. Right? You started in the hospitality industry as well. You spent quite a few years at IHG, if I’m not mistaken.

James Lemon

Absolutely. I’m one of those people that I love to tell the story that’s kind of in my blood. I grew up largely in a bed and breakfast on the Isle of Wight, a tiny island off the south coast of England. My mom used to turn the place over to sailing crews in the summer because it was a sailing town. I slept in the garden, spent the day making beds and making breakfast for people. So I then kinda moved through cafes and restaurants.

But yeah, absolutely. As a grown up, if you like, I went through, got my finance qualification at Unilever, but I came back to the industry and always wanted to work in hotels. I definitely still get this buzz on my former colleagues’ LinkedIn when these amazing hotels are opening or these fabulous resorts are popping up. So for me, I’ve always known it’s an industry I wanna be associated with, and I’m really glad I did my time in operations. I’m really glad I did my time in a hotel chain. I don’t think everyone has to do that, but it’s a really lovely place to work in a provider of travel.

Sebastien Leitner

So how do we as an industry solve this problem that you express? Meaning, the talent recruitment and retention.

James Lemon

I think it’s easy to say, oh, if I had the answer, Sebastien, I would have done it by now. I actually tried to do this for two years. So Atolo was our kind of community and mentoring platform for the industry, which I exited last year. And there is certainly a group of people in travel who share our passion, and they share this kind of sense of challenge. We should be mentoring. We should be giving our time back.

But I think there probably aren’t enough people coming through who that’s really clicked for yet. It is just a job. It is just a paycheck. It is just what they’re doing till their career starts. There are many reasons why that is. I think we probably don’t attract people to the industry in the right way. We don’t really sell it on its benefits of that kind of skill set of creating amazing experiences, that aspect of service, and actually how you should be proud to have that in any career you go on to.

I don’t think we necessarily pay people fairly compared to the money that is being made by some people in this industry. I don’t think we necessarily give them the right tools and tech to use. We still train people up for months on technology they’re just not gonna see anywhere else. So I think all of those things probably contribute, but at its core, there’s other issues like probably some old working practices around working hours and around culture and around how we treat people in their first couple of years in the industry.

I used to say that your first couple of years in any industry is really hard because the hours are longer, the pay is worse, and the learning curve is at its steepest. So I don’t think hospitality is unique. After that, there are some amazing jobs in hospitality, and there’s also incredible entrepreneurship, which is even better. You can go on and do your own thing. But it does worry me that not enough people really see how great hospitality can be, and not enough employers are thinking about the operations, the tech, the experience that their teams will have.

Sebastien Leitner

I’m based in Canada, and I recently came across the Canadian Hotel Association running a huge social media campaign to attract both local but also international hospitality teams ahead of the peak travel period. Whether that’s get a visa and stay near a Canadian national park, or choose a career in hospitality. It’s great to see the industry doing something to attract young talent. Reversely, what lets you sleep easily? What makes you happy?

James Lemon

So on a personal level I have finally started to claim back some hobbies. I’m a parent of two kids that are now kind of twelve and eleven. So I think I’m just beyond that really challenging stage of kids needing you twenty four seven. They can make it to school on their own. They can generally take care of their hygiene.

So the last couple of years, I’ve claimed back two things. One is I’ve always had a passion for wine, and I’m starting to take some wine education. That’s fantastic to just use a different part of my brain for part of the day and not be thinking about work and technology and payments. So it’s really exciting to almost be back at school, being lectured to, writing up revision notes, listening to podcasts.

And then the other is sport. No surprise, lots of us are trying to stay on top of our health. But in addition to running, which I’ve always kind of literally plodded along, I’ve taken up ultimate Frisbee, which is a sport I played at university, which is an incredibly elite top sport for those people who might mock it. If you’re into American football, basketball, soccer, rugby, then let me tell you, Ultimate Frisbee is a phenomenal sport.

Sebastien Leitner

Is it an Olympic discipline yet or not yet?

James Lemon

That’s a great question. I don’t think it is actually, but it’s incredibly inclusive, and it’s great for people who are more all rounders rather than elite in any particular sport. But Saturday mornings, kind of twenty people my age, throwing a disc around in a local park. It’s just incredibly refreshing after the few years we’ve had just to have that banter and friendship. Especially coming out of a pretty challenging pandemic and running my own startup for a couple of years, that was exactly what I needed.

Sebastien Leitner

I’m still looking forward to that age where my four year old son is completely independent. I’m working on it. He’s getting dressed, doing the primary things, but he also loves dad’s attention, at least in the morning, getting him to school. I wish I hadn’t waited so long. I think if I could do it again, I would probably have tried to never give up a couple of passions.

James Lemon

Wine, for example, is brand new to me. And it’s like, oh, I wish I’d always kind of listened to podcasts about this or taken more courses because I think it does just lighten up a different part of your brain. I think it helps your creativity to think about more than just work. And also mental health, right? You have life outside of what you’re doing for most of the day.

Sebastien Leitner

I’m curious, in your role, what’s a common myth about what you do at Stripe?

James Lemon

Stripe’s in a really interesting position in the travel industry because a common myth that Stripe has about itself perhaps is that almost everyone knows who they are and what they do. A disruptive payments technology that’s emerged over the last decade. But actually, outside the world of digital native platforms and startups and technology leaders, it’s really telling as I try and build their profile in the travel industry at events. I still regularly get hoteliers, restaurateurs come to me and say, oh, Stripe. Never heard of that. What is that? So one big myth about me is a big part of my role is probably myth busting and opening the door and explaining what it is.

I think the biggest myth about me is probably you don’t have to be an expert on everything. Coming to a company like Stripe, that’s quite intimidating because payments is incredibly detailed. There’s a huge amount of security, and there’s a huge amount of complexity. But actually, what they were asking for is, could you come and describe and tell us about travel? We actually have seven thousand other people who know a lot about payments, James, but we don’t have anyone who knows what’s on the mind of a hotel executive, what’s on the mind of a technology company that works in the travel industry.

So I definitely love the fact that I don’t need to be a detailed payments expert. I need to be abreast of the industry’s challenges. I need to know how Stripe can play a part, and then I need to have a call on the right people in my external and internal networks to bring together communities to move the industry forward in the world of payments and payments tech.

Sebastien Leitner

That makes sense. You alluded to an interesting fact. Payments is one thing, but how is payments different in the travel industry? Is it different, or is it more complex? Help us understand how hospitality and travel is different in payments than any other business.

James Lemon

I think there’s a couple of things I’ve learned about. One thing is that the place where you buy something and the place where you actually use it is often completely different. By its nature of travel, whether it be hotels or airlines or whatever. The other is that the time that you buy something versus the time you need it is often completely different. And that’s actually pretty rare in payments. If you think about online ordering, you click on something and you’re expecting it there within a couple of days.

Travel’s really different, and that makes it in the legacy of the payments industry quite high risk because you might be handing over thousands of dollars, euros, or pounds, days, weeks, even months, sometimes years before you actually can consume the trip. It also means that information you hand over about credit card details might end up on a completely different side of the world for a hotel to be looking after it safely until you arrive. So there’s a couple of different dynamics there that to the payments industry, they look at travel and go, we really need to understand this better because it’s not like the rest of retail and kind of instant on the spot consumption.

I think the more important thing and the area I love to focus on is that actually the whole of our industry is built on experiences. And we all share this passion to go back to the glory days of travel where your whole journey can feel seamless and frictionless, and you can just get on with doing what you need to do. Whether that’s obviously holidays, where you want to get away with your family and have it be relaxed, or a business trip where you’re only in town for three days and need to be effective.

The role that payments plays in that is quite different because you might be interacting with ten, twenty different companies on that trip. But every time you’re getting out your card and paying in different ways, everyone’s asking for a wallet, can I pay my local payment method, do I use Google Pay and Apple Pay. All this stuff is making it inherently complex. You don’t really have that in other industries.

Some tangible examples: the one taxi in town that doesn’t take a card and you’re late for a meeting, or waiting thirty minutes to check-in to a hotel, or waiting thirty minutes to check out, or waiting in line for an attraction. All of this stuff can detract from just having an amazing travel experience. So there’s probably a vision there of, what if we can make that better? What if we could get a whole team together at Stripe and solve some of those problems? That will bring more people to travel, more travel users to Stripe, and hopefully get the world excited about traveling.

Sebastien Leitner

You must travel quite a bit. When was the last time you used cash?

James Lemon

I was in London yesterday, and the taxi driver said he wouldn’t take a card. And so we were literally scrambling around saying, has anyone got a ten pound note? And doing that classic thing where you watch the meter thinking I may have to ask them to drop us off half a mile before our destination just because it’s the only money we have.

I’ll give you a really good example. I was in Singapore in November, and obviously Singapore and the whole of Southeast Asia, China, North Asia are incredibly payment savvy now. The idea of QR codes and digital wallets and payments, it’s actually a bit of a wild west. Different payments companies and even ride sharing apps, people like Grab, going into cafes and saying, you’re gonna offer more perks, more points if they pay with our wallet.

But I did try and buy an iced coffee just on the way to a conference one morning. I was in a long line of people, and the lady said, we only take cash, and it was about two dollars. The guy behind me said, let me just buy your coffee today. So that reinforced my love of humanity and I got a coffee. Out of all places, Singapore, I expected them to use a digital wallet. It just so happened that in such a contrasting culture of incredibly high-tech and incredibly traditional. I lived there for six months and to be able to go to really high-tech innovative restaurants, but also the local food markets and eat local food, the traditional style, is phenomenal.

Sebastien Leitner

I’m curious on your perspective of the future of travel and payments experience. I’ve always lacked understanding of why I need to carry credit cards in my wallet. I’m hoping that one day I won’t need to carry a physical card anymore. When you think of travel and payments in twenty thirty, what comes to mind?

James Lemon

I definitely share your vision. Part of it is a confidence thing. I only just started going out without my wallet and only a phone probably eighteen months ago, two years ago. I now go on the London Underground, and I can see other people using their Apple Watch. So things are moving fast, and there’s a mix of practicality and an element of confidence.

My vision for payments is definitely that payments become invisible. It’s not inconceivable. You may have to tap a watch, but why should I actually do anything to get a card or cash out of my wallet? You’re starting to see examples of that now. Take something like Lyft. Over the last ten years, they’ve started to build this frictionless, invisible payments experience where I just register my details once, and then I just make my reservation. I’m not really conscious that I’ve said, yeah, you’re gonna be charging my card. And what’s really interesting for travel is that’s a completely unknown amount.

You could do the same in hotels, restaurants. They’ve confirmed your ID at some point, you can then just get in a taxi, go for your ride, hop out, and carry on with your day including tipping. But what’s really interesting is behind the scenes, they have to move that money to a taxi driver. Or if you’re a food delivery app, you have to move it to a restaurant and to a scooter driver. And this idea of digital ecosystems that huge companies have been building on Stripe in the last decade, that’s where I start to get really excited.

Because as a consumer, you might only have one experience, or you just say, this is the journey I’m going on, let me just click once, and then someone else can take care of moving the money around. Imagine if you could do that for hotels plus taxis plus restaurants plus attractions, and you just go about your day. And then at the end of it, someone goes, bang, that’s just deducted. I think we’ll start to see innovators like the Disney Worlds of the world start to get ahead of this. But it’ll be really exciting when we can start doing that on city breaks and include two or three different parts of the travel experience.

And then on the corporate side, why, when everyone goes away at work, can you not do the same thing? We see people like Navan, formerly TripActions, doing exactly that with corporate credit cards and virtual issued cards by Stripe. It’s getting easier and easier to book on behalf of a company. So invisible payments, a frictionless guest experience is definitely where I see things going.

Sebastien Leitner

Excellent. Very interesting. I wanna do a quick lightning round. I just wanna get your first impression of a word. Departure.

James Lemon

Airport waiting rooms.

Sebastien Leitner

Luggage.

James Lemon

Getting smaller.

Sebastien Leitner

Direct versus OTAs.

James Lemon

Indifferent. Experience should win.

Sebastien Leitner

Distraction.

James Lemon

My personality type.

Sebastien Leitner

Digital marketing.

James Lemon

Essential, but misunderstood.

Sebastien Leitner

Social media.

James Lemon

What do I think of social media? Okay.

Sebastien Leitner

Service. We all need more of it.

James Lemon

Housekeeping. Undervalued and too often unsafe.

Sebastien Leitner

Turndown.

James Lemon

Optional.

Sebastien Leitner

A lot of us have spoken at various instances on the pandemic. Travel stopped. Our lives stopped, at least the lives that we were used to. I’m curious, what did you as a person learn from it?

James Lemon

I think my pandemic journey was, I mean, everyone had their own pandemic journey. I was in a really particular spot because prior to the pandemic, my time at Hostmaker, a big home sharing startup, came to an end. So I was about a year into working for myself, advising on innovation and strategy in the hospitality industry. So you can imagine the demand for that stopped almost immediately. I definitely had the rug pulled from me, probably common to a lot of people working in the hospitality industry. Everything just dried up overnight.

I then spent the next two years building Atolo, this community mentoring platform. So my pandemic journey is inherently linked with a really stressful time of my life when I was genuinely trying to do something that I felt had vision and would hopefully have commercial value too. But fundraising, building a team, building products, finding product market fit, driving customers on a B2B side in hotel chains during that time was just inherently different to any other time in history.

So I was definitely exhausted and borderline burnt out by the time the pandemic came to an end. I actually ended up consulting at Stripe. The advisory business was picking up end of twenty twenty one, start of twenty twenty two. But for me, the spring of twenty twenty two was the time where I could see that two years on my startup was enough. I met some phenomenal new people who then went on to become new owners. We exited. It just couldn’t have ended up better really given where I was.

But at the same time, Stripe came out saying, do you wanna interview for this full time role? And it just so happened that it was exactly the right time for me. I’d been working four years on my own, learned a huge amount. I’d always had that entrepreneurial itch, but the time to go back into a company of thousands of people and structure and other people building phenomenal products that I could just help bring to market, it was just the right time. Everything happens for a reason. I genuinely believe you have to go through all of your experiences to be ready for the next one. But it was really tough for me. My relationship with my family and my kids got much tougher. It was difficult, particularly for anyone in this industry.

Sebastien Leitner

A lot of things changed in respect to travel, but I’m curious if there’s any change you’ve seen coming out of the pandemic in travel that you did not expect.

James Lemon

I think if I’m being a realist for the moment, I think we’ve probably gone back to some of the old ways of working faster than I thought we would. People probably say the same about broader society, some of our working patterns, family patterns, and travel patterns. It’s like, oh, we’ve just gone back to how it was in twenty nineteen. So I thought there would be more of a transformation of the way we wanted things to be as a society and maybe as an industry.

There’s certainly still signs of optimism. The trend towards staycations is here to stay. The trend towards more trust based economies, whether that be ride sharing or home sharing, are all things that got accelerated. There’s pockets of excitement like, we probably should be more efficient businesses, should have better cost structures, be more productive, use better tech, QR codes, some of these minor things. But actually, at a general layer, we’ve kinda gone back to how we were before. I think too many groups probably put their head in the sand for a couple of years and then came back and said, we can carry on as normal. I think it’s a shame, and I think we’ve probably missed a window there.

Sebastien Leitner

What would you change?

James Lemon

It’s probably now what would I have changed. I think I probably would have placed a much bigger emphasis in that downtime of, okay, we still have a capital base, we still have staff that wanna do work. Let’s actually do a proper tech transformation that we can fly on for years. The way we work with our guests and that CRM and loyalty piece could be better. The physical experience in hotels, whether that be contactless check-in or just the design and experience, could be accelerated. And the back office technology around property management systems, revenue management, payment stacks, it all probably had an opportunity to use the time we had to go, let’s make this better.

People will say, well, we never knew how long it would last, and we had to conserve our cash. But working with hotel businesses at that time, there were still lots of people around. There were still guests in beds around domestic and staycation. And a lot of the hotel chains don’t own their hotels. So they were still in a position where they probably could have been slightly more innovative. But we didn’t take that opportunity. I think that’s a real shame. My sense is looking at the cultures of the big hotel chains, we’re broadly back to where we were in late twenty nineteen, and I don’t think that much has changed.

Sebastien Leitner

I’m curious if there is a topic or an area that you’re passionate about that I haven’t asked you yet.

James Lemon

Let’s talk about direct versus indirect. This is a really interesting topic for the industry. My view is we should take more experience from the world of retail, which is, yes, it would be fabulous if people came to your stores and came to you direct, but that has to be based on the experience you offer to people no matter where they shop your products or how they shop your products.

I’ve worked with hotel chains who have quite an anti third party distribution strategy. My sense is that needs to be very experience led. Let’s ensure a hundred percent of guests have an amazing experience no matter what channel they come from, and then let’s use our skills in marketing post stay and during stay to lock them in for the future. I think we too often lump together third party channels because actually, in some segments like business travel, you’re almost never gonna persuade a corporate that they should book direct because you have travel management companies and travel managers reinforcing the exact opposite.

So then the TMC is okay, and therefore the GDS is okay. But the GDS is also distributing to that OTA. Well, okay, now it’s okay some of the time. Channel strategies inevitably become way too complex. I think you just have to open up. We are gonna have a phenomenal third party channel strategy. We are just gonna be pouring customers in. Anyone who wants to try our brands can come in. I’m talking about car rental, airlines, hotels, restaurants. Everyone is disintermediated, and everyone is aggregated by someone.

There’s also a huge amount of innovation in that space. I think you need a really nimble channel strategy and allow people in at almost no matter what the cost. But then we use our experience to bring them back. As an industry, we’ve made that far too complicated. And we have over time made third party channels the enemy. But look at how much effort OTAs, Expedia, Booking dot com put into an amazing customer experience online, an amazing checkout. You can pay however you want in any currency with one click. As human beings, that’s obviously the experience we’re gonna flock towards.

I think it’s a real shame more hotel chains don’t look to Stripe and go, wait, we could just have that tech out the box, a one click checkout. Maybe the mindset’s starting to shift now. But until they get there, you can’t constrain someone else for doing an amazing job. You just have to keep upping your game with the in-journey experience, and over time upgrade your booking experience.

Sebastien Leitner

That’s a great point. I’m sure a lot of modern hoteliers want that same frictionless payment and guest experience for their guests as well. Before we wrap up, I want to get back to training and educating and mentoring the next generation. If there’s one piece of advice you’d give somebody starting in the industry today, what would that be?

James Lemon

If I could have two, they’re connected. One is be an eternal student. You need to be on key newsletters like Skift and Focusrite. You should try and have a digital subscription to something like Harvard Business Review or The Economist. You should enjoy podcasts like Masters of Scale or How I Built This. It doesn’t have to be travel stuff, but constantly realize that there are obviously millions more ideas and perspectives and facts out there than you’ll ever have in your head. There’s a huge amount to keep up with just in travel, let alone any subsegment. It’s when you start hearing the same discussion points two or three times that you’re like, okay, I’m starting to master that one.

The second one is make sure you really build your own community. Knowing your community and your place in it is probably the number one thing that will stick with you through your career in everything from asking people for advice or selling to someone or collaborating on something or maybe your next job. Go to events and message people ahead of time on LinkedIn. Send them a LinkedIn invite and say, hey, Sebastien, I’m gonna be at this event next week, wonder if we could grab a coffee. Not as many people as you think actually do that.

Comment on other people’s posts. Don’t just be a lurker clicking like and the odd emoji. Actually write, oh, thanks, Sebastien, I really appreciate your thoughts on that, or share a link to something else you’ve read. It could literally be thirty seconds of your time per post. You will have CEOs and execs writing back and going, thanks, James. It opens up a conversation. I think it’s really important as an emerging leader. Speak up and be present. If you’re invisible, you don’t speak up, then we do risk you drifting off into other industries. This is an industry about people. So if you start speaking up and being noticeable, you will be asked to join podcasts and panels.

There’s an amazing quote from Charlie Tremendous Jones: five years from today, you’re gonna be exactly the same person you are today except for the books you read and the people you’ve met. That’s really my two points. Be an eternal student and build your community.

Sebastien Leitner

Excellent. This is a travel related podcast as well. What’s your favorite travel destination in the world?

James Lemon

I think it probably still is New York. I’ve been there lots of times with work and with the family. I still think it’s a city that has absolutely everything. If you wanna go ice skating in the middle of the city in the winter, it’s free to go to Bryant Park if you bring your own skates. It’s obviously got amazing theater and food. You can get the train for an hour, and you’re at Coney Island on a beach with a fun fair. I love the water and the seas, and just being able to take a ferry and explore different pockets of neighborhoods. That’s always somewhere that’s been warm to my heart. But obviously, London would probably come a close second because there’s no place like home.

Sebastien Leitner

Excellent. James, thank you so much for joining me today. Really a pleasure hearing your thoughts and insights and sharing your wisdom on this fantastic industry.

James Lemon

Thank you, Sebastien.

Sebastien Leitner

Thank you for listening to The Turndown. Don’t forget to subscribe and tune in next week as we discover new exciting guests.