RETHINK RETAIL · 2026-06-30 · 20 min
Key moments - from our scoring
Substance score
36 / 100
Five dimensions, 20 points each
Jeremy Goldman introduces Media in Retail (MIR), a newly launched executive community designed to unite brands, retailers, and agencies around commerce media and customer monetization. Drew Cashmore, who built Walmart Connect into a multi-billion-dollar business, chairs the initiative and articulates the core problem: industry leaders talk past each other at conferences rather than having honest, unfiltered conversations about what actually works. The 365-day model contrasts with traditional one-off events, creating ongoing peer learning through reverse mentorship, emerging leader development, and deep-dive discussions. Cashmore will host Media Mondays, dedicated podcast conversations exploring retail media's micro-nuances - change management incentives across brands, agencies, and retailers; technology investments by mid-tier players competing against Amazon and Walmart; and building direct customer relationships to avoid commoditization. The community positions retail media as foundational to retail operations, not just a profit center, requiring alignment across entire organizations rather than siloed media teams.
Retail media is advertising in and around retail sites using retailer data to target shoppers deterministically and drive purchases. It evolved from a simple profit center offsetting operating costs into a foundational flywheel generating core value for retailers and shaping how people shop and buy.
Remote work, AI proliferation, and job confusion make continuous connection essential. A 365 approach creates ongoing reasons for peers to engage, learn, and mentor each other - especially emerging leaders - rather than experiencing post-conference letdowns.
Change management within retail organizations (aligning disparate incentives across brands, agencies, retailers, and internal teams) and technology investment gaps among mid-market retailers, which are falling further behind Amazon and Walmart due to lower profit motives for innovation.
Gal Shivkiel, who ran Gig Retail with shopper marketing expertise, taught him about customer connectivity and integrating retail media with retail operating models. Stephanie J., Walmart Connect's initial US leader, showed him how to gain organizational alignment and manage 5,000 merchant relationships.
Emerging leaders and younger talent mentor senior leaders on what the organization is missing operationally, complementing traditional mentorship where experienced leaders teach new talent about navigating the space and advancing their careers.
Our reviewer’s read on each dimension, with quotes from the episode.
This is primarily a launch-announcement promotional episode with minimal actionable insight for a B2B operator. The two most substantive points - smaller retailers falling behind on technology and the risk of commoditising oneself by not owning direct relationships - are briefly touched but never developed with depth or specificity.
the rest of market below an Amazon and Walmart frankly, has not effectively invested in technology in a way that allows them to be differentiated against the top
there's a risk that you commoditize yourself. And so, uh, I think core to this is owning that direct relationship with your most important constituents
The framing is almost entirely conventional - community-beats-events, human-connection-beats-AI, 365-vs-one-moment - and there are no contrarian or first-principles arguments. The reverse mentorship mention is mildly interesting but undeveloped.
what I really like about this platform overall is it gives people a reason to talk to each other
playing with things like reverse mentorship, where not only are we providing access to leaders in the retail media space to help mentor emerging teams, but having them actually mentor us
Drew Cashmore is a genuine, high-calibre practitioner who directly built Walmart Connect from an early-stage, third-party-operated business into a multi-billion-dollar network - that's real at-scale operating experience. The episode, however, barely exploits this depth, leaving his expertise largely untapped.
I joined that executive team in 2017 to help build what is now a four and a half, $5 billion retail media business. At the time, it was reasonably tiny. It was operated by a third party
I've lived it for 15 years
There are a handful of concrete anchors - the $4.5 - 5B Walmart Connect figure, the 2017 join date, the 5,000-merchant-relationship reference, and named individuals - but the majority of the conversation stays at a vague, aspirational level with no data on measurement, benchmarks, or outcomes.
what is now a four and a half, $5 billion retail media business
he ran a company called Gig Retail and he has a foundation in shopper marketing. Moved to retail media, built out a lot of phenomenal retail media businesses, especially in the European and Australian market
The host telegraphs answers, frequently self-references, and asks almost exclusively open, flattering questions with no follow-up pressure or pushback. The episode functions as a promotional announcement, not a probing interview - no claim by the guest goes challenged.
I know that's a really hard ask, but, you know, I know you can do it
not to put you on the spot, but also to totally put you on the spot
Computed from the transcript - who did the talking, and the words that came up most.
Welcome to Media in Retail Today, RETHINK Retail officially launched Media in Retail (MiR), a new community built for the people shaping the future of retail media. To mark the launch, Community Chair Drew Cashmore joins Jeremy Goldman to discuss why the industry needs a dedicated space for connection, collaboration, and candid conversation. WHY MIR EXISTS: - Retail media has grown quickly, but there are still too few opportunities for authentic, honest conversations between the people building the industry. - MiR brings together brands, retailers, agencies, and technology partners in a year-round community built around shared learning, fresh perspectives, and real-world experience. - A Community, Not an Event - MiR doesn’t begin and end with an event. It’s a year-round community designed to connect, learn, and grow alongside peers across the industry. - The community is also meant to create pathways for emerging and aspiring retail media leaders, while opening the door to mentorship and shared learning across experience levels. WHY IT MATTERS NOW: - Retail media is becoming a core part of how retailers operate, engage customers, and drive growth.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Welcome to Rethink Retail, the show where we dive into the stories and strategies behind some of the most successful brands on the planet. From brick and mortar giants to E commerce disruptors, we uncover the secrets to their success and deliver the keys to true retail transformation. So ask yourself, are you ready to rethink retail? The future of retail and AI in retail starts now.
Speaker B: Welcome to a very special episode of the Rethink Retail podcast. I'm, um, Jeremy Goldman, your VP of editorial and insights and your host for today. And today we are breaking some massive industry news. The official launch of our media and retail or mir, community. It's going to be a brand new executive community designed to unite leaders. We're shaping the future of commerce media measurement, customer monetization through peer to peer collaboration and thought leadership. Mir, or Mirror, is a dedicated space built to address the industry's biggest opportunity, evolving retail media from a fast growing channel into a mature, measurable business discipline. I'm really excited about this and joining me right now to discuss is our brand new chair for the community, a retail media pioneer who famously helped build Walmart Connect into a multi billion dollar juggernaut, Drew Cashmore. Drew, uh, welcome to Rethink Retail. Really excited to have this chat with you.
Speaker C: Great to see you.
Speaker D: Yeah, absolutely. Let's talk a little bit about, you know, what made you decide to take this chair position for our really exciting new media and retail community.
Speaker C: I think one of the things that's missing in our industry overall is connectivity between brands, agencies and retailers in a really authentic way. And we what's exciting about this opportunity and what I think all of you have seen in this is an opportunity to reinvent the way in which we build relationships in the space, reinvent the way in which we train and educate talent, reinvent the way in which we engage even with our own internal teams in retail. And so I saw this kind of as a way to restart in retail media and move away from some of the noise that is built up over time to focus on the things that actually matter.
Speaker D: It's almost like we're trying to rethink things a little bit, you know, so good. This is why I joined the company. Uh, you know, I mean, it's a matter of the proof is in the pudding. And if you're really willing to rethink the way that things are done and the conversations that are, you know, happening, I mean, I think that there is a lot missing. I mean, not to put you on the spot, but I know that you do go around speak quite a Bit. You're involved in a lot of conferences and industry events and I think sometimes there might be a little talking around issues versus having a honest, unfiltered conversation around really important topics. So did you feel that at all or have you felt that in the past?
Speaker C: Yeah, a lot of the times the noise becomes a strategy and a lot of the time the strategy and noise is driven by very biased people in this industry that have a very singular focus on what needs to happen. And I'm sure I'm guilty of it myself, but I think one of the things that makes this, or what I assume will make this great, is the focus on the real conversations and getting into a little bit more depth than we're traditionally used to in this industry.
Speaker D: Yeah, I think the other key thing that's really nice about the way that I know that you've spoken with our CEO Marie about this quite a lot is how media and retail is framed as a 365 day community versus, you know, one moment in time event. What does that actually look like in practice to you? You know, to have something that's always on? Because I think people always are thirsting for conversation and I always have like a little bit of like a, uh, letdown after I'm like energized coming out of a conference and then it's like, okay. And then I don't, let's say, hear from them for a while. So to me there's always this need for an authentic conversation and not authentic community with, you know, our peers in the space.
Speaker C: Well, if I zoom out and if I think about the thesis that Marie brings to the table with a reimagine of rethink retail, we're in a time now where there's prevalence of remote work, where the AI ification of everything is fundamentally changing our jobs. And it's confusing and it's hard and it's frankly very difficult to connect with people. And what I really like about this platform overall is it gives people a reason to talk to each other. It gives people a platform to talk to each other. And the way, uh, I'm envisioning we do this on an ongoing basis, recognizing that people are really busy in their day jobs, is to create new opportunities for young and emerging leaders in the retail media industry. And people, frankly, that want to enter the retail media industry, give them a chance to talk to each other, learn from each other, engage with each other. And that to me is what a365 platform looks like. The tool that will allow your entire organization and Your entire team to build their skill set on an ongoing basis as opposed to singularly focus on their day job.
Speaker D: And I think when I'm thinking about 365, uh, you can interpret that in, you know, a lot of different ways. I mean, obviously like in terms of days of the year, but like, if you're thinking about like a total, like circular view of like everybody, an all encompassing view of everything within retail media, like there are a lot of players, it's an interesting market, maybe even at a 101 level. There are a lot of people who listen to us for our logistics, content for our AI. Like we cover so many different things. But if somebody's less familiar with retail media, how do you give like a 101 to them in like a minute? I know that's a really hard ask, but, you know, I know you can do it.
Speaker C: I've lived it for 15 years. It's everything to everybody. Retail media at its core is advertising in and around a retail site to a shopper audience, using data from that retailer to target them in deterministic ways such that you can help drive a purchase or help create value for the customer.
Speaker D: Overall.
Speaker C: Retail media started in its infancy as a profit center for retailers to offset some of their operating costs. And it is quickly moved into the total flywheel that generates value for retailers. And why I'm excited about this space and its continued growth is because this thing that we built 15, 20 years ago as just an extension of an ads on a website or a piece of paper in a store has morphed into a, uh, foundational component of retail. And there's so much more to come. But it's become core to the way in which we shop and core to the way in which we buy.
Speaker D: I mean, it's huge. Now. It's very interesting how like six, seven years ago, people were thinking about it as like this fringe. Yeah, like kind of like a nice thing that was just goosing the overall bottom number. And now it's become so incredibly central and yet, I mean, there's so many issues with it, you know, that I know you feel very passionate about. How do you allow this to continue to grow and flourish as, you know, a particular discipline? So I think that's incredibly exciting and I think we actually have some exciting news for people. But I heard a rumor that you are going to be leading Media Mondays for us. You know, a bunch of different podcast conversations with really exciting people in the space. But you really can't believe every single rumor that you hear. So I Kind of just want to like, verify with you, go directly to the source. Is this true or false?
Speaker C: I think it's true. You tell me. You're running the thing, so.
Speaker D: Oh, no, Jackie's running the thing. I work for her. Our producer, Jackie. Yeah, no, no, I think you're doing it and I'm really excited for it. So, I mean, we're kind of like in the formative stages of, uh, filling out what those conversations will look like. But what are you looking to uncover and our audiences uncover, you know, with those shows that you host?
Speaker C: There's a lot of legacy talent and experience in our space that has built retail media as a core foundation of retail into the operating model of individual retailers. That has taken a lot of time, you know, 10, 15, 20 years to get that model close to right. And I still think we're figuring that out overall in this industry. What I'm really most excited about, Media Mondays, and where I think we can take this thing is to have those real conversations and get into some of the very micro nuances of retail media and how you create value within the retail organization or how you educate your brand teams and sales teams in participating in this space. There's a lot of conversation we should be having right now that we're not because we're focused, I think, on surface level conversations. And I'd like us to think about this as a way to dive deep into, uh, all that is retail media.
Speaker D: Yeah, I mean, I think when you're thinking about how to make this a successful, sustainable ecosystem, long term, it's also an interesting place because you've got brands, retailers, you've got agencies that are supporting, you know, like, you have the infrastructure, which is, some of it is like third party, that is woven into how people actually buy. And, um, retail media, I think, is obviously kind of fragmented in terms of you can have pretty good reach, you know, if you just go through one or two players, but then how do you allow everybody else to succeed? So, I don't know. I feel like you're going to get into a whole lot of really interesting conversations, you know, that go down that rabbit hole.
Speaker C: I'm excited.
Speaker D: I want to go back for a second to, uh, you know, something that you were talking about. The AI ification of everything, which we're very much living through right now. And AI is commoditizing a lot of content and events and wondering how do you think that media and retail can stay differentiated in that environment? Because I do think that the thing that you said about, like, human connection and actual human beings. I mean, asking a question of a LLM, um, of uh, how do I get ahead in retail media is not the same thing as having an honest conversation with a mentor who can elevate you in the space. Correct me if I'm wrong, but it just feels a little bit different.
Speaker C: There's a lot of neat things that we can do and frankly a lot of things that we can learn from other communities in the Rethink group like AI and retail. The connections I've seen built from this team over chat and in monthly meetups and meetups in person at different events is to me one of the really solid ways that we can continue to drive these relationships on an ongoing basis. And then playing with things like reverse mentorship, where not only are we providing access to leaders in the retail media space to help mentor emerging teams, but having them actually mentor us and teach us about the things that we need to be doing better and the things that we're frankly missing in the day to day operations that are making this thing less scalable or harder to operate or less appealing for advertisers. And so I really believe that this 365 approach versus the, you know, one or two hits a year in an event is going to make this a community worth coming back to.
Speaker D: I mean, I think that the, you know, in some of our past conversations, one of the things that was really clear to me, which I really loved, is you just feeling like, okay, I would not have gotten here if not for some really great people who helped show me the way. And I think that's something that, uh, yes, we all want connection, we all want to learn from, you know, uh, unless you're my kids, then you don't want to learn from somebody who has more experience than you. But once you become an adult, then you really want to lean into people who've been there and understand things in a deeper way. So I'm wondering who are maybe two people who are demonstrably helpful to you and to your career in retail media and what did they teach you? Maybe it's like a very special episode where we can give thanks to one or two folks.
Speaker C: I learned a lot from a, uh, mentor and close friend of mine, Gal Shivkiel. He ran a company called Gig Retail and he has a foundation in shopper marketing. Moved to retail media, built out a lot of phenomenal retail media businesses, especially in the European and Australian market. And the things that I learned from him are about the connectivity to customer and really thinking about retail media. In, uh, core conjunction with the overall retail operating model. And then Stephanie J. Who is a name most of us probably haven't heard of, but she was the initial leader of Walmart connect in the US market. I joined that executive team in 2017 to help build what is now a four and a half, $5 billion retail media business. At the time, it was reasonably tiny. It was operated by a third party. And Stephanie came in with this unencumbered ambition to change the way in which Walmart worked in totality to support the business of media. And that, to me, was something that I think a lot of retailers are still missing today. That it needs to work in conjunction with the core business and it needs to gain alignment across the organization in a way that has people inspired and engaged and willing to support. And I learned a lot from Stephanie in terms of how to manage, you know, at the time, 5,000 merchant relationships and the most senior people in the Walmart organization to move the needle forward.
Speaker D: I love that. And I know that the, you know, bar keeps on moving in terms of, like, what we're going to be talking about throughout the media Monday segments that you do for us. But I'm curious not to put you on the spot, but also to totally put you on the spot. Whenever people say not to, it means they're going to do it. But this is why we try to, you know, work with people who are, you know, very quick on their feet. So what's something that you're very excited about or one particular topic within the broader retail media ecosystem that you're just very interested in talking about right now? It can be any one particular thing because I know obviously, like, we'll invariably, like, work together to put on some content that may or may be announced soon, but maybe you can give us a, uh, little, you know, peek behind, you know, like, how your brain works and what's a topic that's exciting to you now?
Speaker C: Let me give you two. One is change management within the retail organization. That's something that we're still working through today in terms of how do we engage the broader business like I just talked about, and there are a lot of players that have different incentives within retail and frankly within the brand side and the agency side. And I'd love to spend a lot of time thinking through what are individual incentives and how do we marry those between brand, agency, retailer and then m the teams within those organizations. The other piece that frankly, I'm really obsessed with right now is this idea that rest of market below an Amazon and Walmart frankly, has not effectively invested in technology in a way that allows them to be differentiated against the top. And with continued growth and consolidation happening in the top of this industry, it just means that a lot of the retailers below are falling further and further behind. I want to have deep conversations about what are the ways in which we can effectively compete against the top with innovation in technology, innovation in market approaches and go to market and so on, because frankly, it's what is going to propel this industry forward and make it scalable.
Speaker D: And I know we definitely don't need to talk about it in detail now, but I think you're right. One tricky thing is because you've got a few players that control so much of the market, well, then there's less of a profit motive to invest if you're smaller. But then it also won't grow to the level that it can. And I think the nice thing is, uh, for any upstart, I would just advise them is that you're not ripping up infrastructure to build something new in the way that if you're a lot bigger, it's like a David and Goliath asymmetrical warfare. So how do you find ways to innovate knowing the fact that you don't have the advantage of scale? Because you don't. But I think there are ways to
Speaker C: work around that while still maintaining direct relationships with your most important constituents, your customers and your suppliers. I think that's a nugget that we miss here, is that there are efficient ways to build this in pieces, but that isn't something that is competitive and that isn't something that is connected in a way that will allow you to own those relationships. And therefore, frankly, there's a risk that you commoditize yourself. And so, uh, I think core to this is owning that direct relationship with your most important constituents, because that's what's going drive this thing forward.
Speaker D: So I know I have to let you go in a second. I just want to ask you, what does success look like for median retail a year from now? What's the signal that tells you that this worked? You know, and you can't just say world domination, because that's too obvious.
Speaker C: I think about this in three ways. One is connecting the buyers and the sellers of this ecosystem in a meaningful way that allows everybody to really understand each other's incentives and marry those incentives in a way that's mutually beneficial for the total ecosystem. The second is if we can create tools and systems and the ability for retailers to manage change and brands to manage change within their organizations in a way that propels this industry forward and gets a lot more people engaged outside of core media teams. I think we'll count that as a success. And then finally, and probably most importantly, fostering the next generation of leadership. I think that this effort is about elevating and advancing the craft of retail media into something that can be a career for many different types of people. And that, to me, is when we really made this community a success.
Speaker D: I love that. And we're going to make it fun also, like all of that. But then you're also going to have fun if you're part of it. So. Yeah, no, true. This is really fantastic. I'm going to be looking forward to your episodes, which I know are going to be starting, uh, shortly. You know, I've been asking True, like, can you let me know who's going to be on the first episode? And he's like, no, it's going to be a surprise. I don't want to let you know. So I'm going to find out when all of you do. So very excited for that.
Speaker C: It's a stressful decision. I know you're trying to get me to think it's not, but it's so stressful.
Speaker D: Uh, you know, Rome wasn't built in a day. It's just we're going to keep building on it, you know, week after week. But, yeah, true. Always a pleasure. This is great.
Speaker A: Thank you for listening to the Rethink retail podcast. Don't forget to join us next week week for another episode. And if you're interested in being a guest on the show, apply at Rethink Industries slash podcast guest. That's rethink.industrial podcast guest. Follow us on Twitter @rethinkretail and show some love by subscribing on itunes. Podcast app. Until next time.
Other episodes covering the same guests and topics, from across The B2B Podcast Index.