Where Retail Media, Payments, and Consumer Dollars Actually Go

Commerce is shapeshifting right in front of us, and if you blink, you might miss the moment everything clicks into place. This special edition of Liftoff Journeys is all about what's really happening at the intersection of retail, media, and AI, and why the smartest leaders in the room are rethinking everything from how customers discover brands to how retailers build entirely new revenue streams.

This week I sat down with some seriously plugged-in voices who break down why the traditional marketing funnel is dead (think pinball machines and tornadoes instead), how commerce media is becoming a flywheel for growth rather than just a margin play, and what it actually means to be "AI native" as a brand in 2025. 

You'll hear from Mark Grether, GM/SVP PayPal Ads, PayPal, Ashley Miles, CEO Co-founder, Franklyn West and Christine Russo, CEO Co-founder, What Just Happened, talk about why some retailers are thriving while others are falling behind, what PayPal's transaction data has to do with the future of advertising, and why customer obsession isn't just a buzzword but the actual engine behind every winning strategy discussed in this episode.

Whether you're a CMO trying to future-proof your brand, a retail leader exploring your first media network, or an entrepreneur looking for the signals that separate hype from real opportunity, this one's packed with perspective you can actually use. Tune in, take notes, and get ready to rethink what commerce looks like from here.

Transcript

SPEAKER_03 0:00

Hey, it's Jeannie. Welcome back to Lift Up Journeys, the show where we go behind the titles and into the real stories of how the world's smartest people got to where they are today. Today's a special edition. I sit down with some of the smartest executives and leaders I know, and I ask them where marketing and business are headed and what they're seeing right now that everyone else might be missing. I also ask them to share some advice, advice they wish someone they knew had given them on the way up. Here we are, the error method in motion. Let's get started. Hey everybody, I am here with Christine Russo, host of J host of What Just Happened? Let me do it again. Everybody, I'm here with Christine Russo, host of What Just Happened. I'm so excited to have you on LipTob. I'm so excited to be here. So I'm expecting to get all the inside scoop from possible from the retail industry about technology and everything else that's going on. You're the source. So this is Scoop Away. Scoop away. Tell us what is the latest in retail technology that we need to know about.

SPEAKER_02 1:10

Gosh, everybody rolls their eyes when they hear AI. And that is such a mistake. It's really leading many, many changes throughout the retail industry and many others. So unfortunately, kids, you got to sit through the sessions. You've got to learn from others who are ahead of you. You have to learn and do a lot of research on what's happening. And it's really going to be a mandate coming from leadership anyway.

SPEAKER_03 1:35

Oh, absolutely. Absolutely. A lot of the conversations that we have with CEOs, CMOs, entrepreneurs are all about if if they're older than 40, you know, they've kind of seen this before with digital media. And if they're older than 50, they've seen it before with the internet and email. Do you think this is just a third phase that we're all just going to have to get used to and leverage our advantage?

SPEAKER_02 1:57

It's a third phase, but more not really in that way. So uh during digital transformation, let's say 2017, 2018, for so for some others earlier, like 2012, that was really just the pathway leading us to where we are now. Did we know it at the time? No. And also I think what it reinforces is that we're on a journey. And even AI, where we are now, is a journal. Two two and a half years ago, Gen AI. Two years ago for early adopters, agenc AI. Today, for sort of the the more the ones that are waking up now, agentic AI. Uh, and we're not done. And we're not done. So um what really makes a difference is where your organization is in terms of data management, cleanliness, storage. Um, but also sit still because there are many new solutions coming that can help organizations manage and use that data.

SPEAKER_03 2:55

Well, you've got your finger on the pulse of everything that's happening in retail, and you've got your finger on the pulse of everything that's happening in technology. I laugh that you say it all comes down to data, because is that not the problem of every company for leveraging technology in the world? Good data leads to great results. But what do you think is happening in this world of commerce?

SPEAKER_02 3:15

So commerce is commerce. Commerce is changing really rapidly. Um there's a bifurcation between really advanced technology businesses. So we look at like an Amazon, a Walmart, and then we look at kind of everyone else. Um Home Depot would be advanced. And so we have kind of the the everyone else's that are looking in and saying, I want to be part of that. What's it gonna take? And so they're staffing up their tech teams, they're building out they're bringing in major CTOs and building out their teams, as I said, and going deep into what's called the AI factory. And an example of that is the gap. So the gap is doing many things, and we see a lot of fun creative things out there as consumers and um social media consumers of content, consumers of content, but really what's happening behind the scenes is they're building out their tech in an incredible way. And I'll just add one more thing to put a point on it. Walmart moved as a as a publicly traded company to the NASDAQ. So if that doesn't signal commerce changing into a tech business, so I don't so true.

SPEAKER_03 4:34

So uh there's a lot of conversation around endemic and non-endemic media, non-endemic commerce. Do you think it's inevitable that every business is gonna have to move into non-endemic spaces? Define uh spaces where they're offering products that are not their own in order to attract new customers, they're doing their marketing not just on their own sites, not just on Meta and Facebook, but they're going in and doing unique partnerships. I mean, that's always been the case, but looking at making revenue from selling other people's products.

SPEAKER_02 5:07

Okay, so we refer to that in the biz in my biz as marketplaces in one way. And then also we have what I think maybe might be covered under this is commerce media. So first let's talk about marketplaces. Um there's a lot of success out there, and there are a lot of big companies that are saying, Well, I want some of that pie too. Perfect example, and these are the biggest. So, what does it mean for other people? Not sure yet, but let's just first talk about the leaders because there will then be followers. So Amazon is the perfect example for a successful marketplace, usually successful marketplace. Walmart looked at it and said, Well, we want that too. And they ended up building it out, and it's also grown tremendously. Can't share data, I don't have it at right now, but it's considered very successful. So there will be others, and it is something that is I would say uh another source of revenue because the retail business is really hard. Right. It's marginal like two percent.

SPEAKER_03 6:12

Yeah, it all comes down to the margins, yeah. Yeah, yeah.

SPEAKER_02 6:15

So then you have commerce media, right? Retail media, and that's another revenue stream.

SPEAKER_03 6:19

And how big do you think commerce media will be?

SPEAKER_02 6:22

Well, commerce media, so for example, like PayPal, they're one of they're one of the few, if the only one, that's a horizontal network. Right. So um the ads are built on actual transactions. Very powerful. They're the leader. Um, Dr. Mark Breather uh is the one that built that out. And we're hearing a lot from him during Possible. And retail media, another, you know, it's a heavy lift. It's not something you just jump into. So again, you have Amazon, Walmart, and then lots and lots of others that are saying, I want a piece of that product. So it's hit a bit of a stumble because it's hard to do, and the ROI becomes challenging because you're building it out. So a lot of expenses, yeah, and then it's got a sort of takeoff. Right. So uh I think it will continue to grow. I don't think people will run away from it. And I actually think coming full circle back to the original comment is AI can help build out that.

SPEAKER_03 7:23

Oh, absolutely. There's there's a lot of technology. And interestingly, we had Dr. Mark on the show. So he was talking about everything they're doing at PayPal, and um, we've had some commerce media leaders as well. So it's it's a really fascinating time for anybody in that business. If you had to give a an emerging retailer three pieces of advice on how to get ready for the future, what would it be?

SPEAKER_02 7:45

Well, emerging retailers are now referred to as AI native, right? So we went from having digitally native friends. Yes. That was a trend eight years ago. Um, and they were sort of the golden children of the industry. That moved to direct to consumer as the sort of like, wow, look, they're breaking all the rules, they're doing really well. Think away and Casper and those direct to consumer single mono brands that created this whole new like visual language and profitability model, and then cat came like everything changed it. Here we are today. So AI native um brands that will be coming up are they have an advantage in that they are using technology to create singular messages for every customer. I mean, this is like crazy. Yeah. So um that is something we're seeing big brands do it, but AI native brands are really built for that. That's not a legacy change. Um so that's going to be a very big impact on what we're going to see.

SPEAKER_03 8:54

And do you feel that uh influencers social are gonna be the driver of some of the branding of the new brands? Or do you think it's still gonna be a traditionally driven brand campaign supported by influential social media pockets and traditional digital with some AI personalization?

SPEAKER_02 9:15

One of the things I've learned is that the funnel is more like a pinball machine.

SPEAKER_03 9:20

I'm not hard at described that way, but a pinball machine is perfect.

SPEAKER_02 9:23

So the industry coined it. I like it. I've had them on the show to sort of get into the depths of what that means. And I think that it's very representative of how customers find brands, right? So is it the influencer? Yeah.

SPEAKER_03 9:38

And yes, and yes, and yeah, exactly, exactly.

SPEAKER_02 9:42

Yes, and and many, many other ands, plus not just plus one, plus plus, plus plus, plus, plus, plus. Yeah. I like to say that the funnel is um, you know, it's wide, okay, can come from anywhere, an influencer or wherever. So maybe at the top it's like a pinball machine-esque type of element. But I like to say it's more like a tornado. So it's like shape, same shape as a funnel, but it's like wimping around. It's kind of wrecking things and it's sort of like flinging things all around. That is the stage I think we're in now. And I think we're possible to try to say, how can we contain this? We're all storm chasers, right? Everyone here is a storm chaser chasing that funnel and saying, Well, is it AI? Is AI gonna wrangle the beast and help us be more organized? Yeah, because being organized means we can have solutions. We have the solutions we can plan. We're in a non-planning stage of business right now. It's very hard to plan. And even AI, costs of AI and et cetera, we're very much in a throw spaghetti at the ball and allocate this much money and let's see what happens.

SPEAKER_03 10:46

It's true, it's true. But you know, I I go back to my earlier point. We did that with digital, we did that with email, we did it with social. So this is amazing. And these are times that I think so many of us can can embrace because you're like, everything, try everything, and it's a great equalizer to see who's gonna evolve. And I remember when the app stores first started, and traditional brands were not rating number one on the app store, but you had Smurf Village, where people were spending actual money on digital goods for the first time and battling with traditional brands, and it blew everyone's mind. And we were all like, what's happening? So now we're in that mode again.

SPEAKER_02 11:26

The fight for consumer dollars is uh very, very yeah. Experiences, let's take it offline actually, experiences is taking a big chunk. Um, so when you think about brands and sort of capturing that customer influencer, whatever it is, add on there that experiences is absolutely and I love that because for people like you and I who love in-person experiences and who, you know, the rest of the world has missed them.

SPEAKER_03 11:56

COVID took them away from us, and now they're back with a vengeance. So we got we've got to thank AI for that as well. Uh this was such a fascinating conversation. Thank you so much for taking some time to be on liftoff.

SPEAKER_02 12:07

It's my pleasure.

SPEAKER_03 12:07

Thank you so much. All right, stay tuned, we'll be right back. Wow, I'm so excited to have both of you here with me on liftoff today. Thank you, Mark, for coming. And thank you, Ashley. So great to see you again. So we are gonna have the best conversation about the future of media. And Mark, tell us a little bit about what you do at PayPal.

SPEAKER_00 12:35

Yeah, at PayPal, I run the advertising business. Uh very exciting times, especially given that everything is changing how consumers shop in the future, right? With uh AI all over the place. And uh the good thing about PayPal advertising is twofold. A, we have what is really key in an AI world, which is proprietary data. We have transaction data from 30 million merchants, 400 million consumers globally. We see about 2.7x transactions per second compared to an Amazon.

unknown 13:05

Wow.

SPEAKER_00 13:06

Right? So that's kind of the starting point.

SPEAKER_03 13:08

Say that number again.

SPEAKER_00 13:09

2.7 times of transactions per second compared to an Amazon. And so that's really kind of the foundation of the advertising business. Um, and the second thing is that as consumers are no longer shop just on single merchant websites, they shop wherever they are on the web, um, even now in CTV environments, on LMs, obviously, right? You need to actually bring the shopping experience to consumers. Yes. As opposed to the consumers need to go to a shopping site, right? Uh and so with the payment rails, we have all the infrastructure to do so. And so we've launched a product called Storefront Ads, which as the name says, brings the storefront into the ad, into the consumer, wherever the consumer is uh it's on the open web, it's in CTV, it's in LMs, no matter what a consumer is, he can now or she can now shop.

SPEAKER_03 14:00

It's the most innovative way for endemic media to have legs. Exactly. Yeah, exactly. Yes, I love that. Ashley, what are you seeing in the industry right now as far as innovation with retail media?

SPEAKER_01 14:11

Yeah. So we at Franklin West, one of our verticals is helping retailers grow and scale their advertising businesses and doing so in more of a liquid format where we work with the core internal team of a company and we plug in liquid vetted proven RMN specialists to help that company grow and scale faster and fill the gaps. Um, so one of our best case studies is helping a major retailer build a $1 billion new revenue stream in just three years, uh, three to four years. Um, and so it's a really exciting time to be in commerce media, looking at companies like PayPal. I think you guys are responsible for 30% of transactions globally. So working with a lot of these retailers who are looking to create more relevancy and differentiation in market, thinking about more collaboration between companies like PayPal and retailers, where it becomes PayPal becomes a growth multiplier because what retailers we're finding are so great at is owning their customer data, uh, owning their customer experience, uh, brand storytelling, really being owners of their walled garden, right? Um, but if you think about PayPal and others sitting across so many different categories, regions, uh, so much data at the transactional level, um, this becomes a massive growth opportunity for retailers. So, uh, and especially with the rise of AI and shopping everywhere, I think it's just an incredible uh ripe time for more innovation, more collaboration. Um, my only fear is for the retailers who are late to the game uh and building out their RMN that are actually considering not participating in this space because of what AI is going to be doing and companies like PayPal, it's actually a mistake because there's gonna be so many new ways to build high margin revenue uh on the retail side, which they they need now more than ever.

SPEAKER_03 16:14

Don't you both think that the future of uh commerce media is is almost inevitable, right? You've you've got retailers that have built their businesses out of their store promps and then they moved online, and now they're looking for endemic expansion. And so that clearly has to involve an incredible experience. And I can only imagine as PayPal, you've built brand trust with customers, you've built credibility over many, many years. So seeing, you know, an experience from PayPal ads, especially with the storefront in it, just has to be the next natural thing for many brands. What are you advising brands as they're getting ready for the future of commerce?

SPEAKER_00 16:55

Yeah, I think there are two dimensions. One is the the avertiser dimension, but also that's a consumer dimension. Let me start the consumers, right? Why actually became PayPal what is today? It was all about the trust, right? That consumers had with buying and paying with PayPal when the internet was a new thing, right? Yes. Now buying with an agent is a new thing. How can I trust the agent that he's doing what I want him to do, right? So trust is becoming another key element of becoming successful in AI. And who has the trust when it comes to payments? It is PayPal, right? Right. So in that sense, we will leverage um the heritage of PayPal and trust that we've built as we now move forward into an AI world, right? I think that's very key from a value proposition for uh for consumers. And then your point about the advertisers, right? What we see is that a lot of um customer attorneys, they're now no longer starting with search. They're now starting actually on LLMs.

SPEAKER_04 17:55

Right?

SPEAKER_00 17:55

Eventually you then fine-tune your knowledge on search, but maybe not, right? Uh and so as as an advertising, you need to be where the consumers are, and you need to actually, it's interesting, invest, I would argue, even more now in brand building. That if you are actually in an LLM environment, your brand actually stands out.

SPEAKER_04 18:14

Yes.

SPEAKER_00 18:15

Yeah. Uh and that's again where we can help by having a deeper understanding of the consumer and uh help them to leverage the transaction data to build those kinds of um awareness campaigns and then tie them back to actual performance so we can provide closed loop attribution to our advertisers.

SPEAKER_03 18:33

And that attribution is so key. And I think Ashley, you mentioned it. You said there are so many retailers that are still late to the game, so many brands that don't know how to get started with a retail media network and experience and engagement with someone like PayPal. What are three pieces of advice you would give somebody that thinks they might be late or just starting out what they know they need to do?

SPEAKER_01 18:53

The biggest problem we see is that many late-stage retailers are not identifying why they want to be in this business in the first place. So it's typically out of we want new margin, right? And that's you're not going to be able to build and sustain an advertising business if it's all about you and your margin. That's a part of it, of course, but it goes back to what Mark talked about today and often talks about is being customer obsessed, um, being obsessed with your merchant partners and not treating them like advertisers, treating them like strategic partners, where it's focused around business outcomes. Um, and it's also, as Mark said, around thought leadership and really knowing who are you as a brand, who are you as a retailer or a commerce company, uh, what do you stand for? What's your larger vision for the advertising business that you're you're building? And getting intimately um knowledgeable about the customer experience, how you're strategically solving problems for your partners, and then how you're being transparent around the results that you're driving. So more accountability as well.

SPEAKER_00 20:01

Maybe let me maybe add here something to that. Because yes, of course, when you're talking about retail media, right, and and why everyone talks about retail media, there's on the one hand this, okay, because it's a high margin business, right? Yeah. And our merchants, they are not only need to sell more, but they also need to earn more. Right. And that's why retail media is such a big thing. But the true success actually comes if the retail media business actually is an amplifier of the flywheel of the core business.

SPEAKER_01 20:28

Yes.

SPEAKER_00 20:29

Right. And so, for example, in our case, right, when we now launch the advertising business at PayPal, and when we distribute ads across the open web, they actually are a distribution channel for our buy button. Yeah. And suddenly now consumers are exposed more often to the PayPal buy button or Venmo Buy button. As a consequence of that, they're using the buy button more often. So they're paying more with PayPal and Venmo, right? And that is actually now is amplifying the core business. So it's not just a profit engine. Yes, it is, totally wrong, but the really incentive and also the really buy-in internal, you get if you can demonstrate the flywheel actually spinning faster because of what you do in uh commerce media.

SPEAKER_04 21:10

I want to add to that. Yeah, go ahead.

SPEAKER_01 21:12

So at Franklin West, we often see retailers burying this function within merchandising, within marketing, versus setting it up at the start as a commercial growth engine that it sits incremental to the core business, but that internal cross-departmental task force is bought in from the very beginning, um, which is key. So to Mark's point, that those are the winners, the ones who can set it up uh that sits on top on top of the core business and gets that flywheel accelerating, getting early wins on the board as you're building for the long term.

SPEAKER_03 21:46

Yeah. Now, how do you get this conversation into the executive rooms to get approval to really focus the cross functional uh budgets on something like this?

SPEAKER_00 21:58

Again, I think it's weird. About showing to the executives that it is the flywheel. Right? That's the one key element that is really important. But the other important point is to actually you have to really hire subject matter experts or at least get access to subject matter experts, right? Because advertising might be a new thing to the retailer, but it's actually not new in the industry. Right. So we have done it all over the all over again, again and again and again. So you need to bring in the right talent who know how to actually quickly get this business uh up of the ground and they're not learning as they're doing it. There's no time to learn on the job. Right, right. You have to basically therefore, I think two things are key. You need to show the flywheel and you need to bring in sufficient meta experts for whom it's not the first lawyer. Yeah.

SPEAKER_03 22:46

Now, question for you before Ashley, and then uh um if you were talking to brands, advertisers, businesses, what are the three areas of focus that they can spend their time on to make sure that they're successful at obsessing over the customer? Because I think that's a key part of making your flywheel successful is that customer experience.

SPEAKER_00 23:10

Yeah, I mean the customer experience, right, is fr and I'll come back to the paypal point, right? How can you actually pay with trust? How is it very easy to make payments, right? Uh and and hence for us it's really important, again, if we now run campaigns, that the campaigns themselves feel highly relevant. That's why we use the transaction data to make sure it's the case. But it's also why we build in the buy button into the creative ad units so that experience for the consumer is very seamless and frictionless, right?

SPEAKER_03 23:41

Trust speed is perfect. That that's great. That's great. Ashley, final point.

SPEAKER_01 23:46

Going back to uh the org process and getting these things approved, which can often be the hardest part.

SPEAKER_04 23:53

Yeah.

SPEAKER_01 23:53

Um is typically there is a key decision maker who owns the growth aspect of the business, right? They have some big, you know, growth goal to achieve. Um and getting aligned with them up front, that that early alignment. I mean, we have one right now that's about to go live where the growth leader has then brought in the CFO, the CMO. So that internal task force sits across all these functions, even though the growth leader is responsible for it. In some cases, it's the CMO or the GM. But but they do a great job, the ones who do well, they do a great job of getting cross-departmental alignment. So early on, we bring in liquid, we're able to move so quickly. But we have to understand intimately their KPIs in their day-to-day. What does incrementality look like for each of their business units? And to Mark's point, you start showing the ROI on that flywheel and how it's benefiting each of those groups, and you align their incentives to that success. And then it just starts to take off.

SPEAKER_03 24:57

Well, it sounds like if you start with the flywheel and then you've got internal customer obsession with your stakeholders, external customer obsession with the experience, you're set for success. Exactly. Mark, Ashley, thank you so much for being on Liftoff. We could talk for hours about this. There's no time better than the present to get started. So I really appreciate you both being on the show. That was amazing, right? That's the episode. If you got something out of this conversation, share it with someone who needs to hear it. Hit follow on Liftoff Journeys wherever you listen so you don't miss the rest of our special series. And come find us and follow us at Liftoff Show on any social channel. Want to know which of these guests you'd grab coffee with and why? I'm Jeannie Weldon. Until next, Liftoff.