Lead with Heart, Scale with AI: Bruce Hershey on Modern Marketing

0:00Hey, welcome to the CMO Whisper Show. I'm your host, Steve Olensky. Part marketing practitioner, part ad agency veteran, part journalist. I was a writer for Forbes for 10 years. I've had so many insightful conversations over the years with business leaders, to athletes, to celebrities, to, of course, CMOs. The only difference now is instead of sharing those insights through written form, I'm doing it this way. My guest this week is making his second appearance on the CMO Whisperer podcast. And for good reason. He's a CMO who's helped Fortune 500s, startups, and even a scratch-made pizza shop break through the noise.

0:39He's driven$350 million in revenues from one suit campaign. One campaign,$350 million. He sparked 45 % online growth through AI and built brands that lead with meaning and scale with precision. With over 25 years in the game, Bruce Hershey isn't just a marketer. He's a builder, breaker, and rebuilder. Named CMO of the year, Bruce brings a rare mix of creative courage and operational discipline. But more than that, to me personally, he's a friend and a mentor, someone I continue to learn from every time we talk, including right now. He's back to share what's working, what's next, and how we lead with heart in an algorithmic world.

1:19And while he's never one to brag, let's just say any company looking to level up should be paying close attention because Bruce is more than ready for what's ever next. And it's going to be big. My brother, my mentor, my friend, Bruce, welcome back. Humbly. Thank you so much. hearing all those wonderful things you were saying. You never actually see them or hear them until someone talks about it. So thank you. You are very welcome, my friend. Every word, you know, I love you. We go way back, but let's get into it. I want to, I want the world to learn from you. And I'd love the first thing we're going to talk about because as we're recording this, it's pretty early in the morning and I want to get into why does marketing still get you out of bed every morning?

2:00Yeah, it's because I love it. honestly. I mean, if you think about like, I remember when I got into marketing, I was like, why do I want to do this? I remember like in college, why do you want to go into marketing, Bruce? And I was like, I don't know. It just seems fun. Like, you know, getting a brand to connect with people, it just seems fun. Right. And as I got into it and it was so cool about it is that marketing just evolves every single day because our consumers do. Right. And that means the brain has to. That means our technology has to. That means our thinking has to. Right. And so it's just, I don't know, you have to always be on your toes.

2:36Right. And I think that's what I love about it. Your journey, as I mentioned in the intro, you've been all over the place from Fortune 500s all the way down to a scratch pizza shop and everywhere in between. So my first question is give us the commonalities amongst anywhere and then let's get into what makes things different? Yeah, I think the commonalities of all of it is that I think I've identified that I really love to solve problems. I love to uncover what the next thing could be, right? Or, you know, uncover that opportunity that, you know, we went to market, but just not doing what we wanted to do and just peeling back the onion a few more times to let it get to go and breathe than what it should be doing, right?

3:20I think that to me is a commonality is really fixing, leveraging data, and then, you know, getting the brand in a really good place and then go help in the next one, right? Okay, so now you've scratched pizza shop. Yeah. Fortune 500, right? Oh my God. The commonalities are there. Get into a little bit of, and you know, the differences are going to be numerous, but even I'm fascinated. that I'm sure that people would be doing, what are some things that maybe you learned as being in a scratch pizza shop that you picked up from Fortune 500 or vice versa? Kind of do some comparisons. Yeah, I mean, look, just to take a step back and sort of build off your first question, just leading into this question, right?

4:09Which is, look, I had built, I had broken, I had rebuilt, right? And the one common goal that, for me, it's always about storytelling into growth. To me, that's really where it comes into this. And if I think about the exciting things for me today, it's helping brands lead with heart. Scale with that data and outmaneuver the noise. And there's so much noise today, Steve. There's so much. And, you know, and I'm a huge, huge component of AI. Right. And I jumped on it earlier. I remember I was using it back when I was a Taylor Branson. You know, we called it machine learning. Right. And so it's fascinating how it's come to the commercial side now or the consumer side.

4:58Right. And we're able to start leveraging this and you can build projects. You can start to actually understand your voice and tone. And it's just really cool stuff. Right. So I don't know. I think that there's just a really big opportunity with AI. So I got to excuse me, get into the built, broken, rebuilt. Right. Right. Yeah. I got to juxtapose over, though. And you know this as well as anybody, CMOs on average, you know where I'm going. Shortest tenure. Right. 100 percent. Talk to CMOs who are listening, either who just started or have gotten in going. Like, Bruce, I'd love that, right? I want to do that.

5:35But how can I do that with a short runway? Yeah, it's hard. It's great. I mean, it cuts off to you. It's really hard. And I think is, look, if you're a seasoned marketer, right, you have playbooks, right? And those playbooks, you know, evolve, right? And you can pick them up and bring them with you. But I think is that, yeah, you're right. You have a short runway. I mean, look, I'm just coming off of working with a PE-backed company. And they're short runways, right? And they have goals. Get in and get out. And they want to sell, right? And they're looking for growth. And they're looking for EBITDA.

6:14And it's like, how do you balance both worlds, right? And so what I would say is that get in, understand your plan, not in 90 days, in your first 30 days, right? Like, get it together ASAP. Like if you've got the job, you have a window before you start it, right? Start doing the pre-work then, right? Yeah. You know, now you're not going to know your team. You're not going to know all the different noises within the org, but you're a marketer. You're a seasoned marketer. Like get ready, understand your playbook. You know the core principles. Is the brand in a good place? How's the data being collected?

6:48How's the messaging? Is it creative in a good place? And then pick your least path of resistance, right? Where you can make changes really quickly, like the low-hanging fruit, building from there. But you've got to move quick and build the relationships early on. Not just with the C-suite. Those are givens, right? But who's going to help you, enable you to get these jobs done quicker? Is it in the IT department? Is it in the customer service department? Where is it? Is it in ops? Is it in finance? Maybe someone in finance is going to help you build some more analytical reports. You don't know.

7:19But you got to build those relationships early, build, you know, and get in and move fast because that's what they're looking for. And I would dare I say, and I know you're going to nod your head and agree with this vehemently, if you will, is now with AI, things can be expedited. You can. Right. And I think it's it's being trained to use AI. Right. Right. It's just, you know, we've talked about this. You and I talked about just off of this. Right. You know, if you take it for surface level, you're never going to win. Right. It's still a child. It's still learning. It's still learning you. Right.

7:53It's also learning from the world. So exactly. Yep. So, you know, you have to just continue to coach it and coach it and coach it. And look, for me, I firmly believe it's optimized me by at least 20 percent today. Right. It's helping me with my writing. Right. And I'm using multiple platforms. And I will tell you, if there's anybody out there that hasn't taken any crash courses, you should. Okay. The prompting is the key. Right. And Steve, you know this. You've been playing around recently with this whole, you know, even Jeff Charney came out with something. You walk out of a box. You're an action figure.

8:28Like, it's just really cool. But the prompts enable that to do that. And if you know what prompts to ask, you're not going to get to it. Same things if you're trying to solve a problem. Yeah. When I put the right prompt in there, you're not going to get to the end zone. You're not going to solve the problem. Well, it's the classic. It's the classic, you know, back in when big data came into Vogue, it's the right data in the right data out. It's the same thing with prompts, I think. 100%. 100%. The good news is that it's there. You just got to figure out what the right prompt is, right? Yeah. And as you know, as you were playing around with building your action figure, as you adjusted your prompts and you got to a certain point, you're like, great.

9:05But you also identify that if you use one unique different word, it will change the entire image. Yeah. And you're like, wait, wait, go back. We've all done it, right? No, no. Give me the original. It is. It's fascinating. I want to go back in history for a second with you or more than a second to your days at Tailored Brands. And it was in the intro. $350 million in revenue from a suit. Yeah. I know everybody's. Okay. Like what? How? Talk to a suit. Well, I think it's further than that, right? It's from a suit campaign, right? And so what happened was, is that, you know, Men's Warehouse, Joseph A.

9:46Banks, you know, all the clothes that we have within tailored brands, the fascinating thing is that they're all off the rack, right? And so you come in and we have tailors in there and you can get in there and get tailored up and walk out with a really good suit, right? But as we all know that, and this was back in 15 when we started thinking about it, but it was more about how do we create something more custom? We all want something. And back in the day, remember getting your name inside your jacket? Oh, it's never the guy there. I receive. And that's all cool. But we want to take it to a level.

10:20We want to customize that suit. We wanted the guy to be able to pick the fabric. We wanted to pick the lining. We want to put his name in there. Or he wouldn't have his favorite team inside of the lining. Right. And so we started thinking, how can we do this? And we'd acquired Joseph Abood. So we had a factory in North America. So we knew we could build in North America, no problem. We already had one of the most amazing suit designers in the world under us. So why not do that? And then we started working with our factories. And we're like, hey, there's a really good opportunity. So we came up with a custom suit program.

10:52And that's what it was. It's really understanding, number one, our audience. Would the guy want a custom suit? and we'd be willing to pay for it. How much would he be willing to pay for it? So we had two different ways then. You could buy a custom suit starting at$450 ,000 and then you could go buy a made with some really good fabrics or you can go get a Joseph Aboud custom suit starting at$800, if you will, with more Italian fabrics, if you will. And so you had the best of both worlds, but there was an entry level. And the idea was we wanted a custom suit for every man. That was the goal. And look, you've gone in and bought a suit.

11:31You know you're going to go off the rack and you're going to, you can spend 500 bucks all day long for off the rack, Calvin and Klein suit. But what do you get a custom one for that same price? Right. And so that was the ethos. So, you know, we had to create sales enablement. We had to make sure that the stores were trained. We had to make sure our tailors were trained. We want to make sure that the managers understood that when a customer came in, that that, that was our value prop. We even built custom areas within every single store and men's warehouse and in Joseph A. Banks to ensure when a customer come in, they understood that this was a special treatment for them.

12:04Right? And so, obviously, when we started with our full 360 view, digital, social, we went, you know, TV obviously, we create our, what I call our hybrid sandwich, creative, where we had promo and brand, right? We had a mixed messaging going on because we wanted a customer to understand that brand was so important. but oh, by the way, you can have a little bit of savings too. And when we didn't really launch any savings out the gate with the custom suit program, but we did have our perfect fit program. So, you know, which was the sweetest program in the world, because for every$50 you got, you get$10 rewards.

12:43So think about that. You know, you come in and buy a suit. Guess what? You know, spend 500 bucks. You're going to get instantly rewards. You can go buy more shirts and belts and shoes, right? So the idea is to get them to shop over and over and over again, right? So the average shopper shopped with us about 1.5 times a year. Our goal is to get into two. Guess what? We did it. And the numbers speak for themselves. Just an incredible campaign. And you should be, and I know you are very proud of the work you did at Tower Brands. I mean, it's just astonishing. Steve, it goes back down to the team.

13:11I was obviously the leader, but I had an incredible, incredible team. I had incredible creatives. I had incredible art directors and just production. And of course, you know, having a good agency is obviously really important as well with the ideas. But overall, you know, our merchants, right, our president, everybody was just so in around this. Right. It was just it was great. Not to mention, you know, we had a new talent behind it all. It just felt so good. Yeah, exactly. I can your passion comes out in the way you talk about the team. And I love that. And it speaks to the kind of leader you are that knowing that you're you're only as good as the team underneath you.

13:50Right. And that's 100 percent. A hundred percent. Right. And I think at the end of the day, for me, the takeaway for all of us around this is that the best CMOs think like growth officers. Right. Yeah. We are in credibility by delivering business outcomes, not fluff. Right. So the brand, the creative, that's all great stuff. Love it. It's cool. Right. But that what bills matter. Exactly. Exactly. You said something the other day to me and I want to go back to AI for a second. and I love this. And you said, AI doesn't replace the marketer. It frees us. Yeah. Right. And I'm just going to read something you sent to me because it gives us back time to create, connect, and think strategically.

14:28And we know you and I've talked about this so many times, how many marketers, let alone how many other industries are fearful of AI replacing their job. Right. And I want you to share the story you told me about Piper Scratch Pizza, which is the name of your pizza shop and how you used AI and you increased online sales by 45%. It's incredible, man. Incredible. How did you do it? So, you know, look, I built a model. So, you know, being a marketer, you know, and working across some amazing colleagues throughout my career, you know, I was thinking there's got to be a better trap here. How can you how can we use AI?

15:04We hypers use AI to help us understand what our customers truly crave. Right. So, you know, we emailed them. We did some Facebook surveys. We understand which product to feature. And can we even bundle some pairings with cannolis or garlic knots or cinnamon knots or whatever, right? Or toppings in general. So we did that, ingested all that, and then just started to do some light drip campaigns from email perspective and not offer driven. The biggest trap in I think restaurants is you want to do offer, offer, offer to get them to come in the door. I'm a believer because I was trained at the corporate level that incentives are insidious.

15:46They can kill a business. But we do have three offers per week. So we just capitalize on those offers. No special offers, nothing crazy. The idea was we just wanted to elevate that, but tied back to their interest. Knowing that I have every single purchase of every single pizza, every single customer has bought from us. taking all that, identifying what are the common themes and then targeting lookalikes that same way and bringing them back into the funnel, not just my other customers that were buying from us, but lookalikes that they are friends with as well. It was really fascinating, Steve.

16:26And as I think about, you know, not just the growth, I think about the patience that I needed to do this because, you know, as you quoted me, it frees us. AI frees us. What I'm trying to really emulate there is that, you know, what AI is not, it's not strategic. Let me be 100 % clear. It's not. It will be, but it's not. We humans, if we're given that ability to be strategic, that's where the strategy comes from. What AI can help is tactical. So it frees me from being tactical. It does the tactical elements. I know in my head what I want. I have something now that can execute. Yeah, exactly. Exactly.

17:06And there's the lesson, right, about I think when AI and I think it's still kind of the new shiny toy, right? It's 100%, right? It really is. And look, I think the goal for that is to scale smartly, right, with intent and not to overwhelm, right? Pace yourself through it. You know, like I said, it's optimized me by 20 % with room to grow, but I'm pacing myself, right? I am pacing myself because I know I can't trust it a hundred percent. I can't even trust it 60%. Okay. I'm having to go back and look at it over and over again, but it's still making me a lot more efficient. Exactly. Exactly. God, there's so much to cover here.

17:46My gosh, there's going to be a part three for sure. But I really want, I want you to tell the story about your most recent role at a company called StormSmart, where 200 % social engagement and brain lift. And when you got there, and I will say it for you because humility will prevent you, they were known as Hurricane Protection Company. They're based in Florida, shutters and awnings and all those things. You oversaw into a positioning of lifestyle. right? Yeah. That's a big shift. And I want to start with how did that go over internally? Because that's a big brand pivot. Yeah. I think, look, the company is amazing.

18:30Number one, number two, they homegrown, right? 30 years old, started in Southwest Florida. Great idea. Right. And now it's evolved. But the whole premise to your point was all around hurricane protection. right? And as I got into the brand, I started to look at the brand. What does this really stand for? How did it evolve? How did we get there? Then I started looking at the product. Okay. What is this product? What does it actually do? Are we missing some of the value prop around this? Have we really identified the features and benefits around this? And then number three is, how are the consumers using it today that have bought this product, right?

19:05So Dovendee, You know, the big TAM, right. Analysis also looked into the audiences, look at them and really identified. And of course, like I said, the product identified that there was something that we weren't talking about, which was this lifestyle, right? Which is you can buy their core product, their storm catcher product. And yes, it has that hurricane protection. It's built from cows. It's built from cat five, you know, protection and all that wonderful thing. But what it can do is give you an amazing lifestyle. It can give you an amazing lifestyle. You can shut those things down because they're screens.

19:46Okay. And the next thing you know, guess what? You have an opening that you can enjoy without bugs coming in. Right. You can open up your sliders in your windows and AC won't go out because it blocks that AC from going out. So anyways, I'm going long on this and I'm sorry. But the net of it is that we had to understand the brand. We had to understand the customer. We had to understand the product. Three ways in. We understood that. We knew there was a way in. We started adjusting that through our creative, not just in print and TV, but also in social. And that's where we had really the biggest lift.

20:22We were telling a story. We were showing that this product did more. And the customers that had bought the product that thought it was just hurricane, and they jumped in and they started sharing conversations right they started saying yeah it does i can actually roll these down when it's hot outside and and i can open my windows and i can enjoy it and eat my food outside that's a lifestyle enhancement right and so we we validated the proof to me and i and i know the story well for having you know so close to you is the one of the best lessons to come out of this is for for a lot of brands there are so many i'll call them hidden stories, right?

21:01That are there right below the surface. And it's kind of forest to the trees sometimes. And, and I will, I will give you the props again. I know humility would prevent you, but from pulling back the curtain on all those, Hey guys, we're more than just this. We can do that. And when you pull back that it just exploded. And I think the lesson, and I want you to speak to this for, for other marketers who are working in a, in a given industry, there's those stories are there. 100%. They're there, right? And look, if you think it was easy and you think I didn't get any resistance, right? I did, right?

21:36A lot of history in that company, right? And so, but data doesn't lie, right? So, you know, and look, the takeaway for me on that one is that the customers didn't need really more content. They needed the right message told clearly. Yeah. Right? And so, and consistently, right? And there's a little bit of emotional tension in there, right? That's what they needed, right? And so, look, don't be afraid to lean in. Let the data tell the story, right? To pace yourself into it. You know, sometimes when you rip the band-aid, it burns. But if you slowly peel it, it will be easier, right?

22:17Okay. I want to spend a few minutes kind of asking Bruce Serci to talk to his younger self about what you know now that you wish you knew then. Oh my gosh. And we can, we can spend an hour, right? We all have those. Oh my God. If I only, right. But give us some kind of bullet points of things, you know, now that you wish you knew that. Yeah. I would say be more direct, be more deliberate, be a thousand percent more curious. Right. And I think that's really it. Right. I mean, I believe that, you know, we all have, we can always go back and say, I wish I would have done that. I wish I would have done this knowing what I know now.

22:55But I think the biggest one, and I think I said it with a number, be more curious, right? I think that's the thing is that don't settle. I think there's times in my career where I've settled because I just didn't have the endurance to push one more time, right? Or the resilience, it should say. And I would say it's worth it because when I have pushed that one more time, it's validated that it was worth it. So push one more time. I like that. Give me a good title of your autobiography. Push one more time. Yeah, absolutely. Okay. Last section. I wasn't doing this on our first go round, which is about, oh my gosh, about 18 months ago, but I called the random five and I'm really interested because I know you so well, but I want everybody to get to know you as well.

23:37And these are five random questions to help people get to know Bruce Hersey, the person. Yeah. Okay. And I know you're game for anything. Do it. Number one, if your life had a soundtrack, what would be the opening song? Wow. Okay. What's why I saw Deadpool last night and it just stuck in my head. Okay. There's no wrong answer.

23:59It was exciting the way he did it. Wow. I love it. What's one thing you think people misunderstand about you? I'm a hard ass. When you're really not. Yeah. Okay. What's something you're really good at that has absolutely nothing to do with your career? Bucky. Okay. What's your guilty pleasure that you'll never actually feel guilty about? Oh, my God. And this is not an endorsement. So noted.

24:31And people will laugh, but I'm going to say Swedish Fish. Oh, wow. So bad for you, but they're my guilty pleasure. I don't feel guilty about. I can grab one or two and it's enough. and if I'm stressed, I may grab 10. But I love them and they're my guilty pleasure. I love it. I love it. That's a, yeah. My gosh, that took me back to my childhood, but I love that you still eat them. I know, right? Every now and again. Hey, whatever. There's no wrong. It's worse for you. Exactly, exactly. You would think it'd be chocolate being my last name's Hershey. Yeah, right? Yeah. I have one more question and we're going to do a wrap-up.