Gap was never uncool. It just disappeared. CEO Richard Dickson joins Rapid Response to explain how he’s bringing it back, using the same pop culture playbook he used to resurrect Barbie at Mattel. He breaks down why he tracks “brand love” metrics on a dashboard hourly, why Sydney Sweeney’s viral jeans ad was actually good news for the whole industry, and why the biggest risk a brand can take is playing it safe.
Table of Contents:
- Revitalizing iconic brands like Mattel and Gap
- Why Gap is leaning into pop culture
- Inside Gap's turnaround
- Measuring brand love in real time
- Why missed swings matter when rebuilding a culture
- Connecting profit and purpose through sustainability
- Using AI while protecting customer trust
- Reimagining stores in a digital world
- What it means for Gap to return as a culture-shaping brand
- Episode Takeaways
Transcript:
Relevance is a sport
Note: Transcripts are automatically generated from episode audio, and are not fully corrected for spelling, grammar, and formatting.
RICHARD DICKSON: To some extent, what happened to Gap? We got spooked by some of the swings and ultimately became very safe, and therefore not very interesting. To get people interested, you have to be interesting. Our Katseye campaign was trending No. 1 on TikTok within 24 hours. If we had said three years ago, “Do you think the Gap brand is going to be trending on TikTok, let alone trending as No. 1 in search?” no one would have believed that. If we’re not swinging, we’re never going to hit.
SAFIAN: That’s Richard Dickson, CEO of Gap Inc., the business housing Gap, Banana Republic, Old Navy, and Athleta. I sat down with Richard at the Cannes Lions Advertising Festival in France to understand how he’s applying a playbook he used at Mattel to the challenges at Gap. The secret, he says, is leaning into pop culture. Richard talks about why Sidney Sweeney’s viral jeans ad was surprisingly good for the industry, even though it didn’t come from the Gap, and why he tracks Brand Love metrics on a dashboard every day. Plus, timely lessons around the relationship between profit and social purpose, the need to keep taking risks after failure, and more. So let’s get to it. I’m Bob Safian, and this is Rapid Response.
[THEME MUSIC]
I’m Bob Safian. I’m here with Richard Dickson, the CEO of Gap. Thanks for being here.
DICKSON: Bob, it’s good to be here.
Copy LinkRevitalizing iconic brands like Mattel and Gap
SAFIAN: Before Gap, you were at Mattel when Barbie was a little tarnished, and then brought her back to glory.
DICKSON: Yes.
SAFIAN: You went to Gap when it was also in a bit of a lull. Do you like the turnaround challenge of taking an iconic brand somewhere else? Is that your jam?
DICKSON: It seems I like that pain. Actually, it’s true. I love iconic brands that had a breakthrough and then, over their lifespan, had peaks and pits. I think Barbie is a great example of that. There are others, and certainly the Gap story is one of them as well.
SAFIAN: Do you think about it as renovation? Do you think about it as restarting, refounding?
DICKSON: I think about it as revitalization. To the extent that you have to study a brand’s history, it’s about understanding what made it great to begin with. Why was it interesting? Why were people interested?
SAFIAN: To find that core again?
DICKSON: Yeah, to find the essence, the breakthrough that inspired such success. Along the way, with brands I’ve been a part of, they’re generational. They go through trials and tribulations and a lot of outside influences that change the brand. But ultimately, at some point, those brands either lose their way or reinvent themselves to be relevant. In the case of what I find interesting, it’s getting involved in brands that arguably have lost their way and need to find that revitalized narrative to be relevant again. For me, my experience in doing that has a methodology, but it’s really the execution of that methodology that determines success.
Copy LinkWhy Gap is leaning into pop culture
SAFIAN: So far, the success has been strong. You’ve had nine quarters of positive sales, right? Market value is up to $8.5 billion. And the driver you’ve pointed to connecting all this is pop culture, which for a lot of businesspeople seems kind of soft.
DICKSON: Yeah. I think pop culture sounds simple, but it’s hard. Moving at the speed of culture, staying relevant, particularly for brands that have history, is difficult. In the context of brands with history, these brands started when it was TV and print and outdoor. Being where your consumer is today means being everywhere. That’s very difficult to do. Ultimately, staying relevant is a sport. When you get it right, relevance can drive revenue.
When you only concentrate on numbers and deliverables, a brand can lose its way because you start to make decisions that are financially based, not necessarily narrative- or brand-based. That’s when you start to potentially fragment the dialogue with consumers because you’re driving a commercial proposition, but not necessarily one that really drives consumer authenticity.
SAFIAN: That emotion.
DICKSON: That emotion. Brands are relationships, purely. It doesn’t matter what category they’re in, you have a relationship with a brand. When that brand fragments that in any way, you lose trust. And trust is the foundation of any brand relationship. Once that’s fractured, it takes a long time to regain it. At some point, we lost the storytelling and became more about the stuff.
SAFIAN: The conversation around retail and fashion apparel brands is often that it’s about fashion, it’s about style, and you have to keep up with the pace of style. The clothing itself is what drives it. Obviously, you wouldn’t say the clothing doesn’t matter, but how do those things go together?
DICKSON: Look, the essence of any consumer product business is the product. So you’ve got to have a product proposition that connects to consumers. In our case: fit, fabrication, value, style. Getting the product right is no joke.
SAFIAN: And that wasn’t the first thing when you came in, where you said, “Oh, that’s what I have to fix first”?
DICKSON: There’s no first because it’s really an orchestra. It’s everything from the product to the marketing to the staff to the people.
SAFIAN: To the stores. It’s everything.
DICKSON: The sights, the sounds, everything. The shipping, the logistics. When you have thousands of stores, it’s really a complex conversation internally to get right. So we laid out a very specific agenda with strategic priorities that focused the company, by the way, 80,000 people across the company, around our strategic objectives. The first one was fundamentally that we have to run a better business. We need financial and operational rigor. We need to understand what we’ve got and be more effective and efficient about it. Then run as a retailer with a smart open-to-buy, smart bets, chasing some things, managing the business in a way that is agile but disciplined.
Then it is about cultural relevance. Telling the story about the product and about the brand connects people to that story. Storytellers need to be great brand narrators. When you find a good brand, it’s a good story. Granted, the deliverable is actually the product, because you can drive traffic, you can drive interest, and if people get there and say, “It doesn’t fit, it’s too expensive, I don’t like it,” you don’t have the conversion. The magic happens when you have great product, great storytelling, and great execution. Not everything is going to go right all the time, but once you start that practice, you can create that flywheel.
Copy LinkInside Gap’s turnaround
SAFIAN: For you, you sort of knew that maybe the product wasn’t going to be your personal sweet spot, and that you would bring people in?
DICKSON: I’m not a clothing designer, no. But I think what I realized early on, particularly with scaled businesses, is that it’s a team sport. Sure, there’s vision, and there are leaders who have the conviction to move things along, but you can’t do it alone. So you need to bring in and surround yourself with the best talent, people who are better than you at exactly what you need them to do. I think of myself more as a conductor, bringing in the musicians and creating an orchestra that plays together.
At the beginning, an orchestra is tuning up, and there’s no harmony. But then the conductor starts, and everybody begins to play together, and it’s a magical moment. As a metaphor, when I got to Gap Inc., there was a lot of tuning up. Really good musicians not necessarily playing together. So orchestrating that, bringing in the right musicians to play with each other, and moving it into a more harmonious state is the role I play as the leader.
SAFIAN: And you have a feel for pop culture, too, I think. That emphasis is not something Gap, at least just before, was leaning into, right?
DICKSON: For sure. Look, I think there’s a taste level. We’re in a business where nobody needs us. We have to create want. You create demand. And to some extent, it is a taste-level business. Fashion is entertainment. It’s storytelling. It’s feel, it’s fabric, it’s fit. What we do builds confidence. You look in the mirror, you feel good, and you’re out in the world. If we can do that for our customers, that’s essentially the secret sauce that’s not such a secret.
So I would argue that I certainly have a taste level that can be appreciated, but I would probably think of myself more as an architect of branding. There are edits that need to be made. You used to walk into one of our stores, and arguably there are some stores you still walk into in our portfolio where the message isn’t coming across clearly. We edited a lot of stuff out of our assortment, and all of a sudden you start to see the storytelling. What do the merchants really believe in? What do we want our consumers to believe in, and to share in that experience? A denim shop, a khaki shop, a fleece shop. These are things that speak to consumers without someone necessarily having to take them through it. And I think that is, to some extent, the road we’re on right now.
SAFIAN: I noticed that you hired a chief entertainment officer.
DICKSON: I did.
SAFIAN: Which is not a title you see at most retailers. Is Gap a pop culture brand the way Barbie is? Are we going to see a Gap movie?
DICKSON: You never know.
SAFIAN: You never know?
DICKSON: Yeah. First off, fashion is entertainment. It is. Whether you’re looking at the runways or at sports today, what are they wearing in the tunnel? Fashion is entertainment. Once you embrace that, you have to think about storytelling and what forms of entertainment matter. In our case, it’s music, it’s art, it’s film, it’s events. These are areas where experts matter, and we need that expertise to drive them with authenticity. So of course you need a chief entertainment officer. Of course you need talent that can really take you into those places credibly.
SAFIAN: To authentically align with you.
DICKSON: 100%. Look at the conversation we’re having around Gap today. It’s about music. It’s about fashion. It’s about our content. It’s about our media mix model. That’s the story we’re telling. But then, when you get to our stores or you get the product, you feel like, “Oh, this is my best friend again.” So for us, we have to keep that narrative and storytelling continuously going. That speed of culture today is the price of entry for a brand.
SAFIAN: Unlike some CEOs, Richard acknowledges that his expertise is more about brand orchestration than the company’s core product. So how might AI muddy those orchestration waters, and how can leaders stay motivated to keep taking risks after failure? We’ll talk about that and more after the break. Stay with us.
[AD BREAK]
Before the break, Gap’s Richard Dickson talked about how he’s leaning into pop culture to turn around the company. Now Richard explains why he’s tracking Brand Love metrics at his desk every day and why striking out should never deter a leader from swinging again and again. Let’s dive back in.
Copy LinkMeasuring brand love in real time
Some CEOs get obsessed with watching the stock price all the time, even though few like to admit it. But you’ve said you look at a different metric hourly. I don’t know if this is right: a dashboard called Brand Love?
DICKSON: I do. Where’d you get that from? Yeah, I guess I do.
SAFIAN: It sounds a bit distracting, though, looking that often. It sounds like when I get lost in my TikTok feeds.
DICKSON: It can be. But I find, first of all, retail is detail, and you’re in it every hour. We have a flash we can look at and say, “How are we doing?” And when we’re doing well, you should ask, “Why are we doing so well?” And when we’re not doing well, you ask, “Why are we not doing well?”
SAFIAN: So these are sales numbers?
DICKSON: Well, there are sales metrics. I have a dashboard in my office that has graphs and sales metrics. And then there’s another dashboard that measures Brand Love, Brand Search, and attributes we’re measuring with our consumers in the context of receptivity to our narratives and to our media mix models.
SAFIAN: And you’re tracking this every day, all the time?
DICKSON: We’re tracking it every day, all the time.
SAFIAN: And it’s not distracting, it’s guiding?
DICKSON: I believe it’s the information you need to drive the business. And if you’re not curious about the work and what’s working or not working, this is not a business for you. It really isn’t.
SAFIAN: And you see it that fast?
DICKSON: We see it that fast.
SAFIAN: Which is new in the way, I guess, both the speed of culture and the speed of business work.
DICKSON: Absolutely. You can see it as soon as it hits the marketplace. Even some of our Gap work, our Katseye campaign, was trending number one on TikTok within 24 hours. If we had said three years ago, “Do you think Gap brand is going to be trending on TikTok, let alone trending number one in search?” no one would have believed that.
But with the data we receive, we can find multiple ways of sharing more storytelling, expanding that concept, and being motivated by the insights we’re gathering on a daily basis, which moves the organization forward. We see that with what sells, too. You see when a product sells, and you see when it doesn’t. When it doesn’t, it’s not going to get better. A product that doesn’t sell —
SAFIAN: Take it off the shelf.
DICKSON: Move it through the system. Yes, it’s a markdown, and it is what it is, but that’s the business of the business.
SAFIAN: You know that’s going to happen.
DICKSON: Of course it’s going to happen.
SAFIAN: With all of these things, with brand campaigns, with product, right?
DICKSON: 100%. If we’re not swinging, we’re never going to hit. There are going to be misses, but the objective is to have more hits than misses, and ultimately not reward the misses, but acknowledge that we swung and missed.
So what do we learn from that? Why didn’t it work? That element of dialogue is a really important part of the conversation in our company. And I think what leaders today need to embrace is the ability to feel comfortably uncomfortable. You’ve got to take shots on goal. You’ve got to take swings in order to move the business forward. And the biggest risk of all is not taking risk.
Copy LinkWhy missed swings matter when rebuilding a culture
SAFIAN: Every day you’re getting information that says, “This is going well,” and you’re getting information that says, “This is going badly.”
DICKSON: Totally.
SAFIAN: And how do you know what the balance is when it’s going through that? Or do you just decide, “I’m going to be optimistic and emphasize the things that are going well?”
DICKSON: I’m a consummate optimist, and I love the challenge. If we get bad news or something doesn’t work, it’s a process of editing. That didn’t work. We’ve got to figure out what does. You don’t let it get you down. You let it inspire the next sort of breakthrough.
Sometimes you’re ahead of the game. Sometimes we might’ve been too far ahead, and it was a good idea, strategically well-intended, but flawed in terms of timing. Or strategically well-intended and flawed in execution. And in some cases, there’s dialogue, and a lot of companies have this: “Well, we tried that. We tried that. We tried that.”
SAFIAN: Yes.
DICKSON: It’s not that it wasn’t the right thing to try, but for whatever reason, the execution or the timing was off. Try again. And when you do hit it, that team play and that cultural spark can drive incredible momentum into a business.
SAFIAN: Well, on the flip side, when people are saying, “We tried that, we tried that,” you stop trying anything.
DICKSON: Exactly right. And that’s when the business really stalls. It’s deer in the headlights. You don’t try anything, and you become incredibly safe.
SAFIAN: Yes.
DICKSON: And arguably, that is to some extent what happened to Gap and our brands. We got spooked by some of the swings and ultimately became very safe, and therefore not very interesting. To get people interested, you have to be interesting. And that is ultimately what I think is connecting our consumers back to our brands: we’re interesting.
SAFIAN: And so even the Sydney Sweeney stuff that was a little controversial, that’s okay?
DICKSON: It’s great.
SAFIAN: It’s great.
DICKSON: I think it’s great for the industry. We’re in an industry where, obviously, we want to be the winners, but when the industry is driving creativity, it should inspire better competition. When you look left and you look right and you go, “Well, that’s pretty good, and they’re out there doing that,” you go, “Okay, let’s go.”
So I think we’re inspiring better work in the industry, and I think the industry is doing better work on its own. I think it moves us as an industry forward. And obviously, our goals and ambitions are to be the best of the best, but we’ve got a long way to go before we can claim that.
Copy LinkConnecting profit and purpose through sustainability
SAFIAN: You announced new sustainability goals this year along with the partnership called Get Blue, with Matt Damon’s Water.org. Talk around sustainability has kind of been on the wane. It has not been a hot topic lately. Why do this now?
DICKSON: Sustainability is one dynamic of what we’ll call purpose in the context of Gap Inc.’s brands. We’ve always been purposeful, and arguably, the more profit we drive, the more purposeful we can be. Purpose and profit have an interesting integration. And throughout our history, we’ve always been a thoughtful citizen, if you will, not only of the communities that we live in, but of the world and the consumers that we serve.
Our origin story, as you may know, started with one store in San Francisco called The Generation Gap. And our founder, Doris Fisher, crossed out Generation, and it became The Gap. But the original intent was to bridge the generation gap. And that’s a very purposeful statement unto itself. As our company has evolved with Old Navy and Banana Republic and Athleta and all the things that we’ve done over time, we’ve evolved that narrative into bridging gaps to create a better world.
One of the gaps that we take a lot of pride in bridging is the sustainability effort to bridge the climate gap. Within that, it gets very complicated very quickly. So we’ve chosen water as the leading initiative where we can have real impact. And to be blunt, we can’t do what we do without water. To make denim and denim washes, and to feed cotton — cotton’s a thirsty plant — we need water. So we use a lot of water, and water is a scarce commodity. It’s a responsibility that we have to recognize and do what we can to recycle, reuse, replenish water, and get access to clean water in places where we manufacture our product. So yes, it sounds like a nice-to-do, but it’s an essential to-do. Fifty percent of our GDP is nature. We’re partners with nature. So it is a strategic objective for us.
Copy LinkUsing AI while protecting customer trust
SAFIAN: So I can’t have a conversation with the CEO today and not ask about AI. How do you think about it for your business? How disruptive? I mean, it’s certainly having an impact on culture.
DICKSON: It is an essential part of our lives today. Like it or don’t like it, learn to love it.
SAFIAN: Because it’s going to be here.
DICKSON: It is here and is here to stay. And if we don’t embrace it and acknowledge it as a valuable tool, then I think you’re going to be, particularly for businesses, left behind. We’re going to move to a place where the entire business is based on it. It’s an operating platform. It doesn’t just enable things, it actually is the platform that everything is going to sit on. And we are evolving in that direction. We’re making tremendous strides and significant investments in technology, a lot of which is AI-based.
It is, in fact, impacting our business in a positive way, everything from consumer insights to design and development to the speed at which we can digest information. So I find it an incredibly exciting chapter. It’s a bit daunting. But once you jump in that pool and swim around and get a little warmer in it, I think it’s the practice that we all need to do. Right now, it’s more behind the scenes as a system, but I actually think it’s going to get more and more consumer-facing.
SAFIAN: Does that mean that there are going to be fewer humans working in your store, or—
DICKSON: I don’t think so. First of all, I don’t think we think like that. But I do think that the experience from digital to physical and physical to digital will become more seamless. In the context of us knowing you and knowing your style and knowing who you are and knowing what you bought, it can make suggestions.
SAFIAN: But you have to reinforce that trust element for your brand for me to share all that with you too, right?
DICKSON: One hundred percent. And again, that goes back to the fundamentals of brand, even as time passes. It’s all about trust.
Copy LinkReimagining stores in a digital world
SAFIAN: The retail experience, it’s so varied now. What will a Gap store look like in 2030? Do you know yet?
DICKSON: For me, I think we are constantly making progress, not necessarily perfection. It’s nice to imagine perfection, but every day in retail is another aha moment of something we could have done better. So I think we’re constantly evolving. Even in our remodels right now, we’ve done remodels for Gap, remodels for Banana Republic, remodels for Old Navy. We see progress, but not perfection.
SAFIAN: And the whole way you have to think about it is different. It’s like you’re not going to remodel once.
DICKSON: You’re going to keep remodeling.
SAFIAN: Right.
DICKSON: Every time.
SAFIAN: Yeah.
DICKSON: You also have to think about store design in the context of when it needs to be refreshed again.
SAFIAN: Because it’s expensive to do all that, too, right?
DICKSON: It certainly is.
SAFIAN: Yeah.
DICKSON: These are all things you need to consider. But the reality is, stores are going to become even more important as consumers look for human experiences, for places where we can connect, where you can actually feel the product, try it on, listen to the music, hear the sounds, get the service, and find community. I believe that is going to become more and more important.
And if you look at Gen Z and even Alpha, there’s a return to a bit of analog versus digital. I don’t mean that literally, but I do recognize the value of putting down your phone and having a human experience. What’s happening in sports today is incredible. You see these places where humans are gathering, and it creates emotional connection and unity. I think retail could be a really important part of that process.
Copy LinkWhat it means for Gap to return as a culture-shaping brand
SAFIAN: What do you feel is at stake for Gap right now?
DICKSON: I think it’s the recognition that we are an iconic American brand that shapes culture. And I think we have arguably woken up. We’re a brand that people never stopped liking. They just wondered what happened. “What happened to Gap? I used to go there, I used to love it, and then something happened.” We sort of disappeared for a while.
So I think now we’re back, and we’re back in the cultural conversation. Now it’s a question of what we do with it. And truly, when you think about the word gap, it is the space between us. So what better space today to bring people together than in the Gap between us? We take that seriously. And I think you’re going to see over time that cultural connection and that conversation get stronger and more powerful as we build more of our flywheel.
SAFIAN: Well, our world certainly needs more closing of those gaps, more bridging of those gaps.
DICKSON: No doubt.
SAFIAN: Thanks for doing this today. I really appreciate it.
DICKSON: Thank you. It’s been fun.
SAFIAN: There can sometimes be something shallow and sweaty about a company hungering for relevance, trying too hard, latching onto every viral meme. What differentiates a successful reinvention is genuine curiosity about culture and, as Richard notes, a willingness to take swings that don’t land in the quest for greater knowledge and better understanding.
The deer-in-the-headlights phenomenon that Richard describes — fear of taking action because actions have gone badly in the past — is an understandable reaction to uncertain times, but it’s not effective or inspiring. I followed Gap for a long time, and yet it never occurred to me that the brand could stand for bridging gaps in our world. It’s an appealing aspiration and the kind of relevant storytelling that fits this moment.
So what story are you telling, and how might it benefit from some new twists? If it’s good enough for Barbie and Gap, it might be good enough for you, too. I’m Bob Safian. Thanks for listening.
Episode Takeaways
- Richard Dickson says his specialty is revitalizing iconic brands by rediscovering the original spark that made them culturally relevant in the first place.
- At Gap Inc., Richard argues that relevance drives revenue, and that great product only works when it is paired with sharper storytelling, stronger execution, and real emotional trust.
- He describes leading the turnaround like an orchestra, hiring top talent and leaning into entertainment, music, and taste-making to make Gap feel interesting again.
- Richard tracks sales, search, and “Brand Love” constantly, using real-time feedback to guide faster decisions while insisting that missed swings are part of rebuilding a creative culture.
- He ties Gap’s future to purposeful growth, from water-focused sustainability to AI-powered personalization and stores designed as human, culture-shaping spaces that bring people together.