Beautiful Thinkers: Brian Bennett, VP Creative at Carhartt

Carolyn Hadlock
The Beautiful Thinkers Project
9 min readApr 4, 2018

On the value of building a brand from the inside out.

While I’ve never met Brian in person, after talking with him on the phone for an hour, I felt like I’d known him my whole life. That’s the magic of Brian. He’s one of the many talented Creative Directors that have gone client side. Not because he wanted to cash out and cruise, but because he wanted to be on the front lines of something special.

Brian and his counterpart at Carhartt, Tony Ambroza, work together to tell the stories of hardworking people that wear Carhartt.

Where did you start your career?
I started at Wieden+Kennedy in Portland as an account exec. I quickly learned that I loved creative. I was a creative at heart but didn’t know you could go to school for that. I guess I got in the long line in life. Luckily, they recognized that. Mike Byrne, Brian Ford and James Selman let me write for them on Nike. They treated me like a little bro who needed charlie horses and guidance. They gave me the confidence I could write. It was a great place to grow up.

How did starting as an account person help you as a creative?
Wieden and Nike were intertwined. We were only fifteen minutes apart. We hung out with those people. We were friends. Because I was an account exec, I was inside Nike’s building a lot talking to them about what they wanted to do. I saw how much as a creative you’re told to go sit in a box and think about ideas. The account exec is the one in the beginning. He’s with the client more, learning their business and their problems. That helped me as a creative because I saw how important it was to know what’s going on inside of their world.

Where did you go after you left W+K?
I went back to Chicago to create a one-man agency for Nike since that’s where I was from. I would do projects for them: everything from doing research to writing ads.

I was 28 years old, and I was like, “Holy shit, the good news is you know a lot about Nike, and the bad news is you know a lot about Nike.” So I went back into the agency world, but I hated how far I was from the idea, the person who needed the help.

You get really removed when you have clients in different places. I joined Cramer- Krasselt in Chicago where I worked on Corona for four years. I helped them launch their “Find your Beach” campaign. We’d present a TV commercial in Chicago to the group who owned Corona, and you’d maybe be lucky enough to go down to Mexico to present it. So many groups needed to weigh in on it.

You were guessing all the way through.

I did enjoy my time on Corona. I was winning awards, but I never felt like I had a brand that I could really truly help make it better and solve its problems and live it. I think you gotta live the brand you work on.

“The first mission Tony and I had at Carhartt was to give Carhartt a mission.”

How did you end up at Carhartt?
Tony, the chief brand officer at Carhartt, was my client at Nike. He reached back out to me years later when I was working at Cramer-Krasselt in Chicago, and he was at Under Armour. We did some work for him. When he went to Carhartt, he told me I should come start an internal agency. I come from a really blue-collar family. I love the outdoors, so Carhartt was a perfect fit for me. I’d probably be teaching third grade PE if I weren’t here. I’m definitely in the job I’m supposed to be.

Left: “The clock reminds me someone is out there working every second of the day.” Right: “It’s my job to respect the past as we walk bravely in the future.”

What’s the best part about being on the inside of the brand at Carhartt?
I’ve eliminated people getting in the way of an idea and making it happen. That’s the joy of what we have going on here. I’m constantly making. We can make stuff quickly because we know what the problems are. It doesn’t mean that it’s always the best because we move fast, but it allows the work to be honest. It’s always in prototyping. I don’t have a desk full of 40-page decks of ideas. My favorite thing here is constantly being able to make ideas actually happen.

Has being on the inside allowed you to affect the product?
When I got here, women weren’t much of an initiative. I hired a photographer from ad school. I sent her out to meet women and do research. That was interesting because she came back and said we were designing for the wrong woman. I told her to go find artisans and craftsman. We realized the line we had at the time was a bit too L.L Bean. The colors and the fit were off. We were designing for a suburban mom. We had Jennifer start a blog of her times in the field to capture our learnings. It ended up really helping our product team redesign our women’s line.

Another example is our Force line that I named early in my time here. At the time, the company was diversifying from being a jacket brand with a new line of t-shirts that was about wicking. When the sales team went out and launched it, none of the buyers wanted anything to do with it. They said, “Guys, you’re like the 15th person to market with a dry fit shirt.”

With our background, Tony and I were able to help the company think of their workers as athletes. We helped invent a new category. I spent a lot of time with the designer who was testing our products against Nike and Under Armour. We realized that Nike was designing something for one or two hours, and we need a shirt to perform 10–15 hours.

The premise we came up with was: “Why would you buy a shirt that’s built for 90 minutes of tennis when you need a shirt that’s built for 12 hours of work?” We ran with it. Five years later, Force is in everything that is lightweight, needs wicking and motion management, and is energy-efficient.

How do you stay objective and make sure you’re doing work at the level you want to?
We do 90% of our work in house, but we do work other agencies, like Anomaly, out of NY on occasion. Mike Byrnes, who runs Anomaly, was my first mentor at Wieden. He would let me write when he was the CD on Nike. We’ve always written together. I use him as a sounding board. When I start a new campaign, I’ll go to him to help give me fresh thinking.

Anyone who’s in-house should definitely make sure you’re still working with groups out of house. But also, I’ve tried to work differently with them. I want to give them assignments where they can just go kill it and own it and get inside the walls here and see the pain points of why things aren’t working at retail. I bring them on our shoots so they can understand consumers. Our relationship is not a typical relationship. There’s something to be said about being handed over work from a creative director vs. a marketing manager.

What advice would you give someone like me, a CD at an agency, on how to interface with someone like you?
I’ll tell you a funny story about me when I got here. At the time, they were working with another agency. It was the first time I’d ever sat on the other side of the table. As I watched the agency present that day, I realized they had no idea what they looked like from this end of the table. It was like someone who spent so little time on your brand told you about how much they know about your brand. I can still see it. There’s a way in which people approach you and talk to you about something that’s already so ingrained in you. I wish I had the right answer.

The best thing is understand that the people inside this room know a lot more about their consumer than you do. That’s the first thing. Spend time inside the walls. Before you have all of your ideas, go out with the sales team. I always get the best insights when I’m traveling with our sales guys. I’ll go on a trip with our sales guys, and I’ll come back loaded with ideas. Agencies do a real disservice with nominating the account person and letting them be the only person who gets to go into this world and see. Ask to sit with the product team to learn how they make stuff. That’s the beauty of what I have now. If I’m sitting writing about our jacket, I’ll ask myself why do we have these pockets here? That seems dumb. I’ll literally walk upstairs and ask the design team why we designed it. After I talk to the product designers I find out there’s a damn good reason for that pocket. That would’ve taken me two months to figure out if I was at an agency.

Left: “We spend 100 days on the road living in the dirt and capturing stories of those who proudly wear us. Sometimes you get attacked by porcupines.” Right: “To celebrate or 100 year Chore coat we found hard working people, like Sergeant Preston Jowers, who were older than our 100+ coat.”

Why do you choose to work with friends?
It’s probably one of my favorite things about my job. In the early W+K years, it was a family-like environment because you had all these people from around the world that lived in Portland. So you became a little mini band of people who spent a lot of time together. I come from a big family, too. I like working with people that I love and want to be around. I went away to Alaska with five guys for a month when I had a one-year-old and a two-year-old. If I am going to spend that much time away from my family, I want to like the people I’m with. Also, we shoot documentary-style in people’s homes. When we’re entering people’s real lives in that way, I want them to see that I’m there with my best friend and other people I really care about, and that we want to tell their story. I feel like if I came in with a big ad crew and lights and cameras, I’d scare the shit out of them.

“My favorite project at Carhartt ever. Don’t make ads kids, make beer. It tastes better.”

What keeps you at Carhartt?
The fact that Tony and I have access to Mark Valade, CEO and Hamilton Carhartt’s great-grandson, is the main reason I’m here. I got to write our mission and vision with him this year. That’s his legacy. I’m his autobiographer in a way. I don’t just get the write for a brand. This is a family’s name. It’s their story. I don’t have to be the ad guy. I’m just someone else who’s here who is getting to help move this thing forward as opposed when you come in as the magic guy who’s here to save the day.

We also don’t test anything. I have to get alignment, but we don’t ask for permission and that feels really good. I’ve seen good creative agencies flourish if you give them permission to be creative, smart, disciplined and own the project. If we allowed more agencies to do that, I don’t think we’d be arguing over which model is better.

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