
Loading summary
LinkedIn Advertiser
Flowing ad budget on metrics that look great till the CFO sees them. That's bullspend. And marketers are calling it out in dashboard confessions.
Terrence Riley
I remember telling my boss, it'll be good for the brand when leads were slow. Yeah, it. It wasn't.
LinkedIn Advertiser
Cut the bull. Spend LinkedIn lets you target by company job title and more. Advertise on LinkedIn. Spend $250 on your first campaign and get a $250 credit. Go to LinkedIn.com campaign terms and conditions apply.
Terrence Riley
Bringing more emotion to our brand is now the next chapter of our storytelling because we've been very commoditized in a way. Now there's more storytelling that we're introducing to our brand about us, but more importantly than us, you, our consumer. And taking real life inspiration for so many fans and employees who we're now using their stories to tell our story and your story.
Jenny Rooney
Hi, everybody. Welcome. So good to see so many familiar faces. We're thrilled to have you here in Adweek house. I'm Jenny Rooney with Adweek, and I'm thrilled to be sitting here with Terrence Riley. True story. I have been chasing Terrence for years, wanting him to come to some of our things. He's really such an iconic and legendary marketer, and it's wonderful to have you here. So thank you.
Terrence Riley
Thank you. How much do I owe you for that?
Jenny Rooney
We'll talk about it later. But truly, Terrence has just done what I think is magic. Like, he's brought such magic to brands. Anybody heard of something called Stanley? Stanley Cup? Yeah, maybe some Crocs.
Terrence Riley
You've heard of this thing called Stanley?
Jenny Rooney
There's just a little brand called Stanley, the other Stanley cup and the Crocs, obviously, that he's featuring right now. And. Hey, dude. And honestly, what I think is going to be really exciting is to hear you all learn a little bit more about Terrence and his journey that got him to this place because it's pretty extraordinary when you peel back the layers. But, Terrence, I want to start by asking you, tell me about your walk along the beach this morning.
Terrence Riley
Yeah. So I'm a really, really lucky guy. There was once upon a time I sat where you were sitting. And it's a long time ago now because I'm an old man, but I was wondering, how would I ever get on a stage like that? Like, how would people come and listen to me talk about anything? And I aspired to do that. And so I'm walking over here this morning and I got to see my resume on the beach walk, which is pretty amazing. I saw 14 pairs of crocs, nine stanleys, and four hey, dudes. That's pretty cool. Like, wow, how did this happen to me? Is a really remarkable thing. And it starts with great product, of course, but incredible colleagues and teammates that bring some of your vision to life and then make the vision even better and then make it theirs and then make it yours. So pretty remarkable.
Jenny Rooney
It is remarkable. I mean, how many of us can say that, right? That we literally look at the work we put out in the world on a walk along the beach? I mean, it's just everyday life. People have adopted these brands, and it's become so part and parcel to people's everyday lives. But, Terence, I have to ask you, there's this question here, and by the way, it's ironic that we're here at Possible, because the first question has to do with this concept of possibility. Before I ask this pointed question, you said something to me earlier about how you regard possibility. So can we start there?
Terrence Riley
Yeah. I seem to have an unmistakable sense of what's possible. I don't know how to explain it. I just see something and believe it can be done, and it sounds cliche and almost sounds almost boastful, and I don't mean it to sound that way, but I just have a sense of what's possible. I'm a huge Springsteen fan. I'm from New Jersey, and if I'm going to go see Bruce, my elbows are going to be on the stage. It's like that kind of thing. And I try and bring that into my personal life as best I can, as reasonably as I can for my loved ones, but also to work and see what's possible.
Jenny Rooney
So, in fact, do you want to share with everybody what you were able to leave the Bruce Springsteen concert with?
Terrence Riley
All right. So Thursday was my birthday, and Bruce was playing down here in Sunrise, Florida. Just coincidentally, I was asked to do this months and months before he announced the tour. And so he has the lyrics to 10th Avenue freeze out, which is a famous song, on the stage. And I went home with the lyrics on my birthday. That's a pretty good birthday gift for
Jenny Rooney
a Jersey guy, I would say. So. So is it that nothing is impossible to you?
Terrence Riley
Everything's worth trying and then fail fast, but then scale what's working and do it fast. Give your team's permission to fail. I think that the same thing that was given to me in my formative years of my career, I was given the gift of trust and time by the people that hired me. And I like to think I give the same gift that I received to my colleagues. The gift of trust and time. You'll figure it out. You'll get it done. I trust you to do it. Take as much time as you need reasonably. And if you can't call the ball and if it's working, do more of it, scale it, because that's what the job is. So trust in time is important.
Jenny Rooney
And by the way, I just love your origin story too. You grew up in Jersey, as you said, went to Rider University. You were a journalism major. You got a first job in financial services, is that correct?
Terrence Riley
My first job was at a PR agency in New Jersey, filling in for the receptionist when she went to lunch, getting the coffee supplies for the office on Monday morning before 8:00am because if it was 8:01, you were late and don't come in. And they gave me a little account. I was 22, a little indoor amusement park in Paramus, New Jersey, called Sports World. And my job was to try and get press for Sports World, which was an impossible task because there was no news. Hey, they got a new ball pit. Have your kid's birthday at the diner. Nothing. And then one Wednesday evening, just as I'm ready to go home, my big giant desk phone range. And nobody was calling me at 5:05. And I picked up and it was Alan Mechlis, the owner of Sports World. And he said, terence, get down here right away. Somebody get hurt? Somebody suffocate in the ball pit? Did somebody fall off the roller coaster? And he said, no, get down here right away because Michael Jackson is here. That Michael Jackson story, it got weirder over time that he shut down a kid's amusement park. He was there and he rented the place for the night. Now, I have to confess, Jenny, if I had had an iPhone at the time, which they did not exist, I told you, I'm old. I would have succumbed to viral narcissism and headed down to Sports World with my iPhone to try and get a photo with the King of Pop. But it didn't. So what do you think I did instead? As an account coordinator for MWW Group, whose client was Sports World, what do you think I did as a PR guy? Call the press. I was one of very few people on planet Earth who knew where Michael Jackson was. And I drove it like I stole it. And it ended up where I had the biggest hits in the agency's history. At 22 years old and I can still see the owner, Michael Kempner, who I could text Right now, framing them. He went to Frames R Us in the mall and framed my hits and hung them in the wall. And I was promoted to account director of Continental Airlines just a few weeks later. But here's the coolest part of story. I told this story, part of my own career trek, to a group of young colleagues at Crocs many years ago. This exact story. And after my session, one of my young colleagues who had just graduated our intern program and got a full time gig, she sheepishly knocked on my door of my office and said, terrence, you got a minute? I said, of course, Toria. And she said, I think I have your next Michael Jackson moment. I said, what is that? And she showed me a photo of Post Malone wearing Crocs in a hotel lobby. Magic. And what do you think we did? We called Universal Records, Carrie Macker if Carrie Macker. And we made a deal. And I walked into the board meeting and the CEO's office and said, this guy Post Malone is our man. And if you know, boards, post Malone in 2017 was a scary guy. And I told the team and the board and his senior, if this works, it will be our version of the milk mustache everyone will want to wear and make their own Crocs. And I was right.
Jenny Rooney
So, I mean, marketers love to talk about the concept of risk. And you said, fail fast, but some people can actually do that. And other people just like to say that they can do that, but you clearly do that. Where did that come from?
Terrence Riley
I'm from New Jersey.
Jenny Rooney
That's perfect. That's a perfect answer.
Terrence Riley
Yeah. Yeah. Nobody gets out alive. So you fight for everything. Where I'm from, a parking spot, a line in the grocery store, elbows are up. Like, you just are wired that way to win because. And that's also what the money's for. To borrow the line from Don Draper. That's what the money's for. And you're supposed to win. And so why not?
Jenny Rooney
Have you had a big failure?
Terrence Riley
Oh, God. I've had more wins than failures. Thank goodness. Yeah, some spectacular failures, some are still on the Internet. Well, I signed a major act, and I thought this act for Crocs was going to be a huge star. I thought their shoes were going to be an enormous hit. I thought the property, the film or TV show that they were going to do was going to be a huge hit. And I was 0 for 4. Nobody cared when David Bowie died. I thought it would be a good idea to honor David Bowie by Photoshopping Crocs and that lightning bolt David Bowie logo and posting something about David Bowie. And I was destroyed on the Internet for doing that. And it's still on there. You can probably look it up now. But put your phones down, please. Pay attention. I don't need more mockery. But I did that. And of course, just things that just didn't work out. But largely they were more micro than macro. I haven't had some major embarrassing failures, but there's time.
Jenny Rooney
Well, and I mean, you go back to that, you see around corners, as you've said again, but that's like a sixth sense that so many marketers would love to have, but not all do. How have you honed that?
Terrence Riley
I can't explain it. I do have some weird ability to see around corners. My old CFO used to say, terence will speak it into existence. And I don't know what to do with that. It sounds really cool. I'm flattered, but you know something really weird that's been sticking with me for a few days now. So enough of the Jersey talk. But I'm from New Jersey. Did I mention this? And so Soprano, Springsteen, Sinatra, like the holy S's for me. I've been very fortunate to speak publicly, often on stages all around the globe. And I've always, like, for years, like decades, I've said this just to nobody in particular because nobody's really listening. Said, hey, I'm working the big rooms like Sinatra now. That's like an old mob Vegas kind of joke. I work in the big rooms like Sinatra now. Do you realize I've been saying this for like 20 years? And do you know, tomorrow at 4pm I am playing the Pompeii Room. And you'll never believe who played in the pompeii room in 1965. Francis Albert. How has that happened? That I've said this forever and I'm actually, people say manifesting and all, like, how does that happen to me? But it's happening to me. It happens tomorrow. And so something about speaking into existence or seeing around corners has just followed me around in a very good way.
Jenny Rooney
It's refreshing at a time when measurement, AI, data, all of those things are so part and parcel to the marketing craft right now and so necessary and so fundamental. But we also are living in a time when everybody's talking about, let's just hold on to creativity. Let's just hold onto the human element, which is just so necessary and vital. Brand, right? I mean, consumers are overwhelmed with signals and noise. And so the ones that will win are truly the brand specialists. So how Are you thinking about kind of this moment we're living in? And then I promise we're going to get to talking about Crocs and specifically what you're doing there. But I'm really curious to get your thoughts.
Terrence Riley
Yeah, I mean, AI is exciting. I use AI every day for creative briefs. It's easier for me to describe what I want using AI and actually show folks this is what I'm thinking. And use Sora or now whatever I'm using today because Sora shut down. I can't remember where. Using great agencies to just think of ways to bring AI to bring more feeling to the brand. Next year will be Crocs 25th birthday. And now Crocs has two generations that are Crocs native, like Gen Z and Gen Alpha. Don't know a world without Crocs. We many times were their first shoe. And if you come see my speech tomorrow, I'll talk more about that and my first pair. And we all have stories like that. And so bringing more emotion to our brand is now the next chapter of our storytelling because we've been very commoditized in a way. I don't want to say we invented collaborations, but man, we are awesome at it. But when your brand is Pringles on Tuesday, the NFL on Wednesday, Wicked on Thursday, Love Shack Fancy on Friday, brand starts to become a sea of what is the brand. And we rock at that. But now there's more storytelling that we're introducing to our brand about us, but more importantly than us, you, our consumer. And taking real life inspiration for so many fans and employees who we're now using their stories to tell our story.
Jenny Rooney
And your story is it that the collabs kind of got you where you are and you needed them, given sort of the era you had been living through with the brand.
Terrence Riley
I think there's a little fatigue. It's like Springsteen at the shore. Like, hey, Springsteen at a bar in a shore. Again, it's like, hey, another collab from Crocs. And so we have to just be careful with that and make them all more special. Which we did with critical and commercial acclaim just a few weeks ago with Lego. We created LEGO Crocs that we just didn't make enough of them. The world wants them and your finger will hurt from scrolling the amount of incredible free press we got about the LEGO classics.
Jenny Rooney
But this concept that you're talking about, you know, after years of writing cultural tailwinds, how do you sort of recapture your own narrative that's a lot more nuanced Arguably, and it's a little bit harder to do. So can you share some additional examples of like, literally how you're doing that right now?
Terrence Riley
Sure. Thank you for asking. We launched our first brand anthem this year, which is just a beautiful piece of work that really invites the world to let their human out. It's two mannequins that come to life because a store associate put crocs on the mannequins and so it'll make you cry. It makes me cry every time I watch it. This specific moment just gets me right here. One of our associates, Devin, she lives in an apartment complex in Denver. We're based in Colorado. And on her floor there was a pair of Crocs outside of another stranger's door every night. And she just decided to be the gibbets fairy. Gibbets, as you know, are the charms that go in one of the 26 holes. She would put gibbets in this stranger's Crocs. And when she told us that idea, as it already has in your minds as marketers, that's cinematic. And so it's already an award winning reel shorts for us that now people have begged for a sequel. Where Do They Fall in Love Over Gibbitz? And so Charmed to Meet yout is now nominated for a shorty that didn't exist in November and is already now out there. And a sequel may or may not be in the works. So it's those kind of things.
Jenny Rooney
Heard it here first.
Terrence Riley
Yeah. And then of course, TikTok Shop. So as I said earlier, we were just named. I was out in Los Angeles last week to take the team to In N Out Burger. Because when do you go to In N Out Burger in Los Angeles after you win an Oscar? So we got a little bit Michael B. Jordan in us and we got our TikTok Seller of the Year award and I took the team out to In N Out Burger to celebrate. But it's an example of whether it's real shorts or TikTok Shop and live streaming like Crocs, we've always been innovative. Our product is innovative. And we continue to push the boundaries and test and succeed where we're bringing home awards as well as hearts and wallets.
Jenny Rooney
Yeah. I mean, how far the brand has come because, you know, you have, I think your own version of all press is good press, you know, all reaction is good, even when it's negative. And, you know, even in the early days, I mean, Crocs were called ugly. But you actually leaned into that talk about that philosophy and how that continues to inform what you do.
Terrence Riley
So I bought my first pair of crocs in 2005 at a kiosk in the lower level of the Garden State Plaza in Paramus. So I wore Crocs before I was paid to wear Crocs. But years later, I became the cmo. And when I became the cmo, there was a meme on the Internet that I printed and hung in my office. It was the only thing that hung in my office. It was literally thumbtacked to the wall and the meme was a photo of Crocs. And it said, those holes are where your dignity leaks out. Laugh if you want, but that's not fun to read when you're the CMO of that brand. So maybe check yourself. But as Reggie Jackson, the famous hall of Fame baseball player, said, they don't boo nobodies if you're memed. What does that mean? Pick on us. Lean into ugly. Lean into. Your dignity leaks out. So I knew we didn't have an awareness problem because we're memed. We had a relevance opportunity and that's what we flipped. Thanks to an amazing team and Toria Roth knocking on my door and say, terence, I think I have your next Michael Jackson moment.
Jenny Rooney
Love it. So where are you now with the Crocs brand and how are you making sure that you're maintaining, frankly, what's become its icon status versus just having a series of moments?
Terrence Riley
Sure. So we're going from like our consumer gen Alpha, Gen Z. We're going from belonging to becoming. We're maturing along with her. We're her first shoe. She just doesn't want to wear the classic all the time. She might have moved beyond volleyball practice. Now she's now a young adult and we had to grow with her. And so the storytelling for the brand is becoming even more paramount. As I said earlier, it's not just a sea of collaborations to maybe get your attention. With this one, Love Shack Fancy. And yours with the NFL and yours with Pringles, we might get that. And we're always going to do that with excellence. But now it's a broader brand story because we are around the globe. You can't walk anywhere. And I've been fortunate. As I've said before, the airport test is no different than the beach walk test. I look around to see what are people wearing. Like you might. And I see Crocs on every corner of the planet. And I've been to every corner of the planet.
Jenny Rooney
I just wanted to point out as well that you actually are an example of a marketer who came back to the brand after moving to the president role at Stanley. I think you have a really interesting take on titles. And again, I think everybody in this industry gets sort of caught up in titles and specificity of role. And you've taken an arguably unlikely path, albeit that president at most companies often means president of brand. Right? You're overseeing the whole brand strategy, as you did at Stanley, of course. Any thoughts, perspective and philosophy with regard to sort of a career path that marketers should think about or not think about?
Terrence Riley
When they map, it's not linear. The graph doesn't go this way, it goes this way. And embrace that. I was a young guy, reasonably young, 32 years old, a young family. I was the vice president of marketing for Prudential in New Jersey, which is a major employer, Series 7, Series 63, to market financial products. I was like, I hate this. No offense to anyone in financial services. It just wasn't for me. And I got a call that company was moving from Dallas, Texas to Mawa, New Jersey and nobody wanted to move to Mawa, New Jersey. I can't even imagine why. And I took a job as a director of marketing for Foot Action. So a VP of marketing for Prudential to a director of marketing for Foot Action, the now defunct sneaker store that many of you might have grown up on. And ready for this one. Within three weeks, I was on stage with Destiny's Child. That is a true story. I have a photo with Beyonce's arm around me. That is an absolute true story. How great is that? I was marketing long term care insurance and now I am, like, on stage with my boo.
Jenny Rooney
Yeah. Oh my gosh, I love that. By the way, my first job was writing about long term care insurance.
Terrence Riley
Sorry.
Jenny Rooney
And nursing homes.
Terrence Riley
We have come so far, you and I.
Jenny Rooney
This is a little more fun, but everybody should buy long term care insurance if you haven't already. No, seriously. So best advice you would give other marketers, especially as they're thinking about breaking into culture in this way. And what was a mentor that sort of guided your way and informed your philosophy on marketing?
Terrence Riley
I take risk, fail fast, and scale it. Will Smith, not the Fresh Prince, but Will Smith is the most important man other than my father in my career for sure. Will Smith. He hired me at Foot Action and then when Foot Action went belly up, he moved to St. Louis to become the SVP of marketing for Famous Footwear. And he called me up and said, ryles, you got to come out here. I said, I'm not moving to St. Louis. God bless you. Said, I'm not moving to St. Louis in five years in St. Louis later, he used to say, drive it like you stole it. So drive it like you stole it. Somebody gave you the keys. What are you doing with them? Like, who cares if you fail? Like, this is not heart surgery. It's marketing. You should be having a blast. You should fail fast, scale it and drive it like you stole it. And that's usually what works. And when you're passionate around it, do it. No different than my car fire video that you've probably heard about or seen at Stanley. She posted on Wednesday that her car caught on fire and that her Stanley still had ice in it. And I saw it on a Wednesday. I was watching sports and I was scrolling, texted the team or teams, the team, whatever I was doing in 2023. Have you seen this? And they're like, yeah. So I wrote the team back that night and I just said, I'm going to buy her a car. And the next morning, I went into the office, I asked Chloe to come into the storage closet where all our Stanleys were to make it look like a backdrop. Chloe had the phone that had the TikTok account linked to it. And I took the phone and I responded to Danielle and I said, I'm going to buy you a car. And I went about my day and someone texted me, said, hey, you're blowing up on TikTok right now. And 100 million views later, we added $50 million to our Q4 forecast from that video and made the brand famous around the world, where everyone on planet Earth knows that's a Stanley by name. And so when I can say that I helped create a proprietary eponym, Q tip, Xerox, Kleenex, Stanley, that is better than the Beachwalk. That's better than the money. That's better than any article that's ever been written about me except the ones in Adweek. That I can say that and so can my team. Because when I joined Stanley, I was like, we work for Stanley. But no. What? You work for Stanley. It's like saying you work for Disney. Same thing happened with Crocs. That's the best part of this, is taking people with you.
Jenny Rooney
And I can say no more. On that note, that was really fabulous, Terrence. Thank you so much. We cannot wait to watch where Crocs goes from here. If you want to watch innovation, watch Crocs.
Terrence Riley
So thanks for spending your afternoon with me. Thank you for listening to marketing Vanguard, part of the ad Week Podcast Network and Acast Creator Network. You can listen and subscribe to all of Adweek's podcasts by visiting Adweek.com podcasts. Stay updated on all things Adweek Podcast Network by following us on Twitter at Adweek Podcast. And if you have a question or suggestion for the show, send us an email@podcastdweek.com thanks for listening.
LinkedIn Advertiser
Flowing ad budget on metrics that look great till the CFO sees them. That's bullspend and marketers are calling it out in Dashboard Confessions.
Terrence Riley
I remember telling my boss it'll be good for the brand when leads were slow. Yeah, it it wasn't.
LinkedIn Advertiser
Cut the bull. Spend LinkedIn lets you target by company, job title and more. Advertise on LinkedIn. Spend $250 on your first campaign and get a $250 credit. Go to LinkedIn.com campaign terms and conditions apply.
Podcast Summary: Marketing Vanguard — How Crocs Turned "Ugly" Into Cultural Cool ft. CMO Terence Reilly
Hosted by Jenny Rooney (Adweek), May 28, 2026
In this episode of Marketing Vanguard, Jenny Rooney sits down with Terence Reilly, CMO of Crocs, to discuss his extraordinary career journey and how he led Crocs from a brand mocked for its "ugly" shoes into an icon of mainstream and cultural cool. Their conversation delves into taking risks, the power of manifesting possibility, embracing both failure and virality, and the evolving role of storytelling and emotion in building brands. They also discuss Terence's leadership philosophy, experiences across brands like Stanley and Crocs, and how authenticity and human connection continue to drive marketing in an AI-driven era.
Walking Among His Work (02:00)
Terence’s opening anecdote of walking along the beach and seeing people wearing Crocs, Stanleys, and Hey Dudes (the brands he’s worked on) set the stage for a discussion about impact and gratitude.
Embracing Possibility (03:16)
Terence discusses his intrinsic sense of what's possible, likening it to his devotion to achieving the best seat at a Springsteen concert and bringing that optimism into leadership.
Manifesting & Speaking into Existence (10:04)
He touches on the power of speaking dreams aloud and watching them materialize, such as performing in the same venue as Sinatra after years of referencing it as a joke.
Fail Fast, Scale What Works (04:26)
Terence advocates for giving teams 'trust and time', failing fast, and doubling down on what works, crediting supportive mentors for shaping this philosophy.
Formative Career Stories (05:16 – 07:50)
On Failure and Risk (08:22 – 09:52)
Terence candidly shares both micro and macro failures, including a misjudged celebrity partnership and a much-criticized David Bowie tribute, and underscores the importance of resilience and learning from them.
Owning "Ugly" & Cultural Virality (16:15)
Addressing the “ugly” meme culture, Terence describes the pivotal moment when he chose to lean into the ridicule rather than fight it.
From Collaborations to Storytelling (12:00–14:06)
Staying Iconic, Not Just Viral (17:23)
Nonlinear Paths and Titles (19:02)
Mentorship and Giving Back (20:36)
On Taking Risks & Failure:
On Brand & Relevance:
On Virality and Transformation:
On Employee Empowerment:
On Storytelling:
| Timestamp | Segment/Theme | |----------------|---------------------------------------------------------------------| | 01:58 | Reilly’s beach walk and brand impact reflection | | 03:16 | On possibility and manifesting success | | 04:26 | Leadership: trust, time, permission to fail, and scaling wins | | 05:16–07:50 | Michael Jackson moment & Post Malone/Crocs genesis | | 08:22–09:52 | On handling failures and public backlash | | 10:04 | “Speaking it into existence” and the Sinatra Room story | | 12:00–14:06 | Transition from collaborations to insightful, emotional storytelling | | 14:06 | Introduction of Crocs’ brand anthem and Gibbets Fairy story | | 15:15 | TikTok Seller of the Year and live selling innovations | | 16:15 | Embracing the “ugly” meme; Memes, ridicule, and brand awareness | | 17:34 | Evolving from moments to enduring brand status | | 19:02 | Perspective on titles and nonlinear career moves | | 20:36 | Mentorship, “drive it like you stole it,” and the Stanley car fire | | 22:37 | Creating a proprietary eponym and the pride in building icons |
The episode embodies Terence Reilly’s candid, self-deprecating Jersey humor and underdog optimism, with Jenny Rooney offering an enthusiastic, insightful, and supportive interviewing style. The conversation is filled with humility, actionable wisdom, and behind-the-scenes stories that bring both marketing strategy and human experience to life.
Takeaways for Marketers
For Further Listening:
Tune into more episodes of Marketing Vanguard for stories from the industry’s forward-thinkers and brand builders.