ANNOUNCER: Please welcome Stripe’s Chief Business Officer, Jeanne DeWitt Grosser.

JEANNE DEWITT GROSSER: Hello everyone. We opened the day covering Stripe’s advanced payments engine, and the stream of innovations we’re bringing to market to increase conversion rates, evolve your business model, and put AI to work across your stack.

If you think about what makes Stripe unique, it’s our ability to bring together the products we develop with the insights of our users and the underlying innovations of our partners. It’s our users, all of you who are going to turn the innovations we just heard about into customer experiences.

Your best practices enable the Stripe community to stay at the forefront of the internet economy. And it’s in working side by side with our partners, often years in advance of a public launch, that we figure out what the future might look like for global commerce and money movement.

As Will said, it’s a team sport. So I want to spend the next 30 minutes learning directly from payments and industry leaders, individuals who can share tangible insights into how they’ve turned Stripe’s economic infrastructure into delightful customer experiences and new revenue streams, and who also might just have a bit of a crystal ball into the trends we’ll all be discussing here at Sessions 2025.

Before we jump in, I’d like to take an informal poll. No apps, no devices, no opportunity to check email or Slack. Just hands, how many of you have planned to adopt a new business model for the first time in the next couple of years? New marketplaces, platforms, adding subscriptions? Alright, lots of hands out there.

So it certainly turns out you’re not alone. Earlier this year we surveyed thousands of companies to get a pulse on the kinds of business models they plan to launch for the first time. And they told us they’re building subscriptions, new SaaS products, platforms, and marketplaces.

I want to pause for a second here. Turn to your right, turn to your left. I realize that’s the opposite order. I realize we also just made you do this in keynote number one, but this is huge. One in three of you are going to change your business model in the next couple years. So the world around you is certainly changing.

We’re seeing rapid business model changes and customers are also demanding changes in how businesses do business. For example, 10 years ago, ecommerce really just meant credit cards. Now it means providing access to 100+ payment methods around the world. And consumer preferences are changing all the time.

Let’s take buy now, pay later. They’ve grown to nearly a hundred-billion-dollar market in less than half a decade. And with what we’re seeing in Gen AI, we can only imagine the number and extent of changes we’ll be discussing at Sessions 2025.

To unpack all of this, I’d now like to invite two companies that have successfully launched new business models in the midst of changing consumer expectations to the stage. Please welcome Anu from Sotheby’s and Aanan from Wayfair. Welcome, incredibly excited to learn from both of you. So we opened with the theme of new business models and both of your companies are adding new business lines with new business models.

So I’d love to start there. Anu, you’re adding a marketplace at Sotheby’s. Tell me more about what you guys are doing.

ANU RAMANATHAN: Yeah, so Sotheby’s is a 280-year-old auction house. We are in the process of evolving from that into more of a generalized marketplace. So big areas of investment for us.

One is what we call the fixed price business. We have now a luxury segment that we sell at fixed prices, not auctions, obviously. And the second thing is we’re opening retail locations, what we call maisons or salons in some of our key locations across the world. And with that also, we’ve added a bunch of new categories that appeal to new audiences like sneakers, NBA jerseys, so constantly evolving and adapting to the new world.

JEANNE DEWITT GROSSER: Awesome and Aanan, Wayfair, classically known for ecommerce for furniture.

AANAN CONTRACTOR: Yes.

JEANNE DEWITT GROSSER: But you guys are adding brick and mortar, so tell me more about that change.

AANAN CONTRACTOR: Yeah, so at Wayfair we truly strive to be the destination for everything home. And as you mentioned, we put so much effort to build our assortment and selection, not just for furniture and decor, but also housewares and home improvement. And so as I step back and think about our customers and how do we meet them at wherever they are shopping, physical retail and opening stores was a natural transition for us.

So, in record speed, since 2022, now we have eight stores open for all of our AllModern, Birch Lane, and Joss & Main brands. And I’m super excited, on May 23rd in I would say less than a month, we are opening a 150,000 square feet, first Wayfair mega store in Chicago. So, exciting times for us to go from digitally native ecommerce kind of brand to in store and omnichannel.

JEANNE DEWITT GROSSER: Nice, well, that’ll feel even bigger than the stage does up here. So how mission critical is it for you all to get payments right for these new ventures and the customer experiences you’re trying to create?

ANU RAMANATHAN: Yes, for us, you know, Sotheby’s is in the business of trust. Trust is so important to us that we could actually put it on the balance sheet. Relationships with our clients go for decades, 40, 50 years of our collective journey. So, and you’re talking about a very discerning client base, right? They choose the finest objects in the world and you’re talking really large price points.

Like think $2 million, $3 million. The larger, the most expensive painting we sold last year was about $138 million. So for us, getting payments right is kind of the core. It builds that trust to bring these clients back to us and to build kind of that intergenerational trust that we’re trying to generate.

So for us, it’s two main things. It’s around the flexibility that we offer them, payment methods, people can be, you could be bidding from mainland China in an auction that’s being held in New York City. And the other thing for us is it needs to be flawless. So it’s really very core to our business.

JEANNE DEWITT GROSSER: Absolutely and big differences between brick and mortar and online. So what are some of the things that have been keeping you up at night in that shift?

AANAN CONTRACTOR: Yeah look, I think most of our customers have immersive shopping experiences, so they fall in love with the item, it’s for the home, it’s so inspiring, it’s so emotional with that. So after falling in love with what you want to buy, payments just need to work frictionlessly, right? And so the way I think about this is it needs to be simple, it needs to be helpful, and it needs to be secure.

So when I think about this from a unified commerce perspective, it just needs to blend. I have my digital wallet; I should be able to take that to my store. I have a project that is big, I want to apply for, you mentioned BNPL and financing. That should work whether I have a credit line already available that I want to use in store or I want to apply for a new financing. So from lending to loyalty, it’s all about the payment choices and frictionless payment inside the store, card present or not.

JEANNE DEWITT GROSSER: Yes absolutely and Anu, I think the average AOV in the industry is like 50 bucks. At Sotheby’s, I think it’s like hundreds of thousands if not millions. So a little bit of a different…

ANU RAMANATHAN: Yes, ball game.

JEANNE DEWITT GROSSER: You know, need, as you mentioned around flawless payment. So, tell me a little bit more about how you’re achieving that.

ANU RAMANATHAN: So for us it’s mainly about giving our clients a bunch of flexibility, like I mentioned. So that’s functionality, right?

JEANNE DEWITT GROSSER: Yeah.

ANU RAMANATHAN: It’s the ability to pay by whatever mode they choose. It’s whether they want to add on, whether they want to pay by card or through their debit, or if it’s a wire transaction, we have to kind of bring all that together and reconcile all of that, right? So for us it’s about driving that convenience to the client and it’s also about keeping it simple, you know? And so the third piece is reliability for us. It is super important for us to get that right.

JEANNE DEWITT GROSSER: Yep. So before Stripe, what were some of the challenges that you all were facing in launching these new business lines? I’m assuming, Anu, starting with you specifically around marketplaces.

ANU RAMANATHAN: Yeah, so for us prior to Sotheby’s, we had many problems, but one of the problems that we had was basically like lack of options for a client, especially online.

The pandemic changed a bunch of things for Sotheby’s. One of the things that it changed was a bulk of our bids actually come from our online visitors now. And so for us, we had to set up a, we have to kind of have a payments and checkout experience that kind of matches the expectations, right?

So for us, it was a huge challenge to take anything that was debit related for us. We couldn’t do that with a prior provider. And the other thing is reconciling like I said, China UnionPay, I think I mentioned this year before, for us, like Chinese clients are significant bidders across, and they have different limitations based on what the government there restricts them from doing.

So for us, working through those challenges has been a huge pain point that Stripe is helping us resolve.

JEANNE DEWITT GROSSER: Awesome, and you talked about when you’re having the brick-and-mortar experience you really want it to be integrated, but I’m sure there are challenges along the way in creating that unified experience.

AANAN CONTRACTOR: I think as I mentioned, we were going on a very aggressive schedule to launch these stores and coming from a digitally native side, we do have our payment platform. So the priority there was speed to market and with Stripe Terminal, it was just kind of plug and play, almost like that.

I was just talking to Dave and Rob from URBN backstage that for us, if we have a big store opening, I’m not kind of going up and down about that because of Stripe Terminal, that takes 100% off our in-store payments, it unifies the experience. It’s the same architecture and the platform that’s scaling whether online as well as in our store, so that’s beautiful.

JEANNE DEWITT GROSSER: Yep, so you started talking specifically about some of the things you’ve done with Stripe. Anu, in building a marketplace, you guys could have built out all that functionality in-house, but you went with Stripe Connect. What drove that?

ANU RAMANATHAN: Yeah, so for us mainly the first thing is, it’s about expertise. We are experts at art. We are experts at auctions, but we do not know payments and we don’t want to be in the business of figuring that out. Second to us, it’s the opportunity cost of that time, right? We have certain things that we need to build. So we are thinking of more immersive auction experiences. We’re thinking about “How do we bring the galleries to life on the site?” We would rather let the experts do what they’re good at, and Stripe is an expert at this, and we would like to let them kind of handle this piece of the puzzle for us. So it’s mainly around that.

JEANNE DEWITT GROSSER: And Aanan, Wayfair has long invested in ML and AI. And so how are you thinking about shifting that as you continue to partner more deeply with Stripe?

AANAN CONTRACTOR: I think what Anu was saying resonates a lot. Our entire shopping journey needs to be hyper-personalized, that’s where I guess the delight and inspiration and emotion that I’m talking about comes truly alive.

So when I have to step back and think about our payments journey and our fraud protection, that’s where I always kind of step back and think from the perspective of, where is the reach that gives me the best of the decision and the quality of the decision and the signal that we were talking about this morning in a keynote and the ROI of resources and the reach of the data—the scale with our collective businesses and customer from the data perspective that partners like Stripe can have, we cannot reach that independently.

So that’s where it is always going to be build versus buy consideration and hybrid portfolio of ML models that we deploy and leverage throughout the customer journey. Not just to protect ourselves with the use cases like identity or account association, but also improving the entire shopping journey experience or a return experience, what we can offer, leveraging some of these signals that are available to us.

So the Radar announcement this morning is also close to my heart.

JEANNE DEWITT GROSSER: Good yeah, we’ll take it. Awesome well, thank you both for your time. I really loved hearing about the importance of customer trust.

I think hearing that trust is something you can put on your balance sheet is probably something most of us should aspire to, and certainly the fact that the payments and the customer experience are inextricably linked. So thank you again for joining us.

AANAN CONTRACTOR: Of course, thank you for having us.

ANU RAMANATHAN: Pleasure.

JEANNE DEWITT GROSSER: Now we’re not quite done yet. Our next set of speakers are industry leaders in particular; they’re ones who I view to be two of the most innovative partners and market makers. I know that hearing from them will give you a sense of where the industry is headed so that you can bring back these insights and learnings to apply them to your business.

And with that, I’d like to invite Vanessa from Visa and David from Klarna to the stage.

First and foremost, thank you so much for partnership, from both of you. I’ll just dive right in. David, you and I probably talk weekly at this point.

DAVID SYKES: Yep.

JEANNE DEWITT GROSSER: I think the last time we got together in person was in New York, and I remember you telling me about how Sebastian, your founder and CEO, is now spending eight hours nonstop on nothing but AI every single day of the week.

So I would love it if you could talk a little bit about what Klarna is doing with AI and both the things that have been exciting about that, but also some of the challenges in sort of being at the forefront.

DAVID SYKES: Yeah, sure, look, and it’s a huge focus for us at the moment, there’s no question. Earlier this year we launched our AI assistant, and the results are pretty incredible. In its first month, it dealt with 2 million individual customer requests.

It’s basically doing the work of 700 agents. But I think what’s really exciting is, it’s not just an efficiency play, the quality is better. CSAT has improved, time to resolution has gone from 11 minutes to 2 minutes. And so we’re seeing a lot of success.

The thing that gets us excited, I think, is it’s not changing our direction. What it is doing very meaningfully is, there have always been a lot of things we’ve wanted to do, but there have been technical limitations. And I think for the first time it feels possible to do some of those things. Having a true financial assistant, having a true digital shopping assistant, all of those things feel true or feel achievable in a way that they haven’t previously.

And not achievable in a year or two years, like achievable in the very, very near term. That’s exciting and look, it’s not all easy though, right? Like the, the challenge you have is the LLMs we’re working with are very, very good at getting you an 80% accurate answer and very, very bad at getting you 100% accurate answer.

And so we spend a lot of time, and it’s the stuff that people don’t focus on. We spend a lot of time just on the underlying data schema and making sure the data is accurate, the information is consistent. That’s been a challenge, but something that I think we’ve made a lot of success with.

JEANNE DEWITT GROSSER: Yeah, I think we’ve had a similar learning as we’ve been building out our own foundational models. Vanessa, a lot of the emphasis on AI right now is the upside of these new experiences.

But I think one of the things those of us in payments are also paying attention to is it’s definitely going to open up some new fraud vectors. And so that’s something we’ve been collaborating on. Would love to get a better read on some of the things Visa has in store for AI to help us all combat fraud.

VANESSA COLELLA: Yeah, absolutely. I mean, I think we all think about fraud, but at Visa it’s something we wake up in the morning thinking about. We think about during the day and when we go to bed, and we’ve actually been using AI and machine learning for more than 30 years to combat fraud.

In 2022, we stopped $27 billion of fraud on the system. But as you said, you have to constantly evolve. And with Gen AI, we’re investing for a couple of reasons. One, we think there’s real opportunity to continue to make those fraud models more robust, more resilient, because bad actors will use all these same tools. But second, which I think is really important is, it’s not just the fraud side that’s going to change, it’s also how people shop and how people transact.

So if you think about the fact that the models have all been tuned to a set of shopping behaviors that we’ve all understood over years and decades, as those behaviors change, that will also necessitate changes in the model. So I think of this period that we’re going into as kind of the messy middle.

Like we’re going to have old shopping behaviors and we’re going to have new shopping behaviors and commerce behaviors, and we’re going to have to ensure that models are adept at handling fraud across both of those. And that’s part of the reason that at Visa, we’re investing $100 million dollars in a venture fund, specifically focused at Gen AI, so that we are working with the most cutting-edge companies out there.

We really think this is a space where it’s not only about your internal capabilities, it’s also about partnering, like partnering with Stripe. So we’re excited about both what we’re doing within Visa, but also how we can bring advisory services, partnerships, etc., as we all navigate this changing landscape, both on the fraud side and on the commerce and transaction side as well.

JEANNE DEWITT GROSSER: Yep, you’re talking about changing behaviors and I think everybody in this room is also trying to figure out what are other ways we can drive top-line growth? And so I thought David, maybe we start with you here.

One of that is tapping into new demographics. I think a lot of folks are still trying to figure out Gen Z; I know few companies who have figured it out better than Klarna. How do you really think, what is it that you’re doing that’s made you so effective with that audience?

DAVID SYKES: Yeah, look, thank you. I think we really think about it from a brand perspective and from a product perspective. On the brand, if you zoom out, like what is the broader demographic change that’s driving, that buy now, pay later growth you were referencing.

I think it is the fact that younger consumers in particular feel just differently about traditional credit. So we have very consciously tried to build a brand that looks different, feels authentic, feels fun, we’re pink, everybody else is blue, they’re blue because someone in the ’80s decided blue was the color of trust.

JEANNE DEWITT GROSSER: Got blue behind us.

DAVID SYKES: We got blue behind us. But like we really think that the authenticity of the brand is really, really important. And I describe our industry as one that has many companies, but very few brands.

Visa is a great brand, Stripe is a great brand, but most consumers don’t know what they’re paying with. We’ve really tried to build a brand that can forge an emotional connection with a consumer in the same way that American Express did but just with a different demographic; we’ve really targeted a younger audience. And then on the product side, just as it’s an industry with many companies, few brands, it’s a very transactional industry. And no disrespect meant, but nobody opens up their Bank of America app and expects an exciting experience.

It’s a very transactional experience and we just have a different ambition. We want to save a customer money, we want to save them time, all of those transactional things.

We would also like to spark some joy. And so we’ve spent a lot of time just focusing on building a product that feels more intuitive to a younger consumer that feels more engaging. So it’s the combination of those two things, I think, building a brand that consumers can relate to, that they can trust, they can feel good about, and then making a product that just feels very, very relevant. And the combination of those two things has worked really well for us.

JEANNE DEWITT GROSSER: Awesome. I know a lot of us have been used to operating in a more stable macroeconomic environment. COVID starts and sort of in subsequent years, there’s just been a lot more dynamism and Vanessa, I think Visa’s economic reports that you all put out have been one of the things like I look for and always read through the day you guys publish it.

So, would love to get a read on some of the bigger trends you guys are seeing ’cause you often are at the forefront of the customer transaction data before the rest of us really see where we’re going.

VANESSA COLELLA: Yeah, it’s something that because we operate so globally, we are able to watch those trends. And I guess just a couple I would pick out, right now, we’re now seeing outside of the US about 79% of face-to-face transactions are actually Tap to Pay. And that’s really important I think in particular in this audience because what’s underneath that number is that you’re seeing more and more small, what used to be cash transactions, moving into other modalities.

And you see that, you see payment volume in the US is up 6%, but internationally it’s up 11%, cross border, it’s up 16%. All of that is sort of pulling on “How do we continue to make sure that people have more options in terms of how they want to pay.”

I was listening to some of the presenters earlier talk about embedded finance. This is something that we’ve been talking about for years and years, but we feel is at a real inflection point. That’s why you’re hearing it on so many stages right now, because compared to that payment volume growth that I just talked about, we anticipate that embedded finance in the next 18 months is going to be a $7 trillion market.

That market is growing 24% annually. So when you start to think about that notion of bringing more ways to pay, having more places to pay, having more options in terms of how individuals and businesses want to transact, that’s where a lot of that growth is coming from. And to bring it full circle to those small merchants I talked about at the beginning, when you think about embedded finance, what you’re really doing as you bring those transactions closer into the companies is you’re increasing liquidity across the long tail of the system. And we can talk about that for hours, but what that’s going to do is just improve the working capital situation, the ability for small businesses to grow.

So it’s something that at Visa, as we think about sort of being the best way to pay and be paid, if we can together as a community, help get that liquidity across the long tail of small businesses as well as large enterprises, we think embedded finance will be a real unlock there. So something we’re looking at closely.

JEANNE DEWITT GROSSER: Absolutely, we published our annual letter about a month ago in March, and Patrick and John said, “We anticipate the world of 2034 will be meaningfully different.” Would love to get each of your takes on what will be meaningfully different about it then. David, why don’t you kick us off?

DAVID SYKES: Sure, look, we had this vision about five years ago of what we thought the future of financial services would look like. And it really is a scenario where you’re sitting at home and your Alexa goes, “Hey Jeanne, we found you a cheaper mortgage. Just say yes, if you would like us to shift for you.” And in that world, who do you want to be? And we decided we wanted to be the digital assistant. And so I think where you’ll see a lot of innovation and time spent from Klarna, it’s like, how do we become that everyday partner for a consumer from a shopping perspective, from a financial services perspective, whatever it might be.

And the rationale behind that is if we can create a really differentiated, personalized experience for a consumer that’s relevant, timely, interesting, that will unlock an enormous amount of value for our retail partners.

We are just a network. We’ve got 150 million consumers on the one hand, 30 million of them using our app every single month. We’ve got a half a million retailers on the other. And we spend a lot of time thinking about how we connect those two audiences; that’s sort of the value creation piece for us.

VANESSA COLELLA: So first of all, I’m terrible at predicting the future. So I don’t exactly know what things are going to look like 10 years from now, but I will tell you that if we look at just trends that we’re seeing today and where those might carry over, one thing I think is really important in the here and now that is going to be important 5, 10 years from now, is how we encode transactions.

So if I just look at what Stripe and Klarna and Visa have done together, Klarna, I think you’re one of the top token requesters through Stripe, 21 million tokens, that’s something like $1.7 billion of safer, more secure payments. And if I look into the future, I think we’re, as an industry, going to start to think more and more about how do we safeguard, how do we ensure resilience and reliability, but do that to your point earlier of what clients want, what customers want in a way that doesn’t make sort of baggage on the payment, but actually makes it so that you can be sitting there in your living room accepting a mortgage or conducting whatever transaction you want to.

And so we spend quite a lot of time at Visa on those infrastructure building blocks for what we think will pave the way for the kind of experiences that you described.

DAVID SYKES: Yep, totally agree. Hey, and can I just say like a lot of what we’ve been able to achieve, we have only been able to achieve because of partnerships like we have with Stripe and the technical foundations that support a lot of the big ideas that we have are only possible because of what we’re able to do together. So, thank you very much.

JEANNE DEWITT GROSSER: Thanks, really appreciate that, David. Sounds to me like next year I get to say, “Hey Klarna, find me a Stripe Sessions wardrobe.”

DAVID SYKES: Yep.

JEANNE DEWITT GROSSER: And maybe we’ll be announcing that we are tokenizing all the things. So thank you both for joining me on stage.

VANESSA COLELLA: Thank you, Jeanne.

DAVID SYKES: Thanks.

JEANNE DEWITT GROSSER: So to recap what we’ve learned in the past 30 minutes, one, enterprise leaders are looking at new business models to help them rapidly address shifting consumer expectations. Two, the era of Gen AI is upon us, but there’s no 80/20 when it comes to accuracy in financial services. Companies need to invest in their payments data in order to get it right. And then three, AI will unleash new fraud challenges we’ve never seen before, but partners with massive networks will be able to combat that. We’ve got a number of breakouts lined up to dive deeper into these questions. Highly recommend you guys check out the payments roadmap this afternoon and make sure you stop by the expo hall to get a glimpse of AI at work. We’ve got robot stone carvings, prompt engineering, dubbing, and more there.

Thank you very much for joining me and enjoy the rest of your conference.