This is part of our 100 Creative Directors interview series. It has been edited for length and clarity. To return to the series homepage and browse other interviews, click here.

What is the role of a creative director, in your experience?

The job description can change quite a lot from place to place. I’ve spent most of my time as a creative director in essentially a creative-art director role. This was at Playboy, where I was really tasked with bringing all these creative and brand pieces across the company together to create a consistent experience.

As a creative director in-house at a brand that produces a high volume of content and products, brand consistency is the most important thing. At Playboy, I learned to cover all these different parts of the company — e-commerce, licensing, editorial — and ensure the brand was consistently intertwined with each touchpoint. It’s storytelling. For a brand that’s been around for decades, it’s about continuing to push that story forward but not deviating from that history.

At Playboy, we were really accountable to the audience — that Rabbit Head means different things to someone who was a fan of the brand in the 80s than to a younger person walking into Pacsun to pick up a shirt. But connecting everyone that interacts with the brand and the brand itself, there’s a throughline that you can’t break.

My challenge was, how can we make sure that we're telling the Playboy story in the way that the brand is represented consistently at every level — visually, through copy, and through all the products that we put out?

What’s the most challenging part of maintaining that brand consistency, across all these touchpoints and audience segments?

Early on in my career at Playboy I was told that Hugh Hefner would always describe the Rabbit Head Logo as essentially a Rorschach test. 

So, if you see the Playboy logo and you think that it stands for sexual freedom and female empowerment versus something like objectification or pornography, that says more about you as a viewer than it does about the brand and its values. As a creative director at Playboy, it was my job to create my own nuanced view of the former — building on that legacy of sexual freedom and female empowerment by gathering information from Playmates past and present, as well as coworkers who’d been there for many years, sometimes decades. It was then my duty to codify that information and pass it along to new people coming into the company, or any contractors we’d work with.

For me, the challenge of maintaining that consistency is a balance of understanding that nuanced, multi-perspective history, as well as understanding that brands should evolve and working to ensure that the Playboy brand continued to evolve. What allows you to evolve a brand is understanding the very core, foundational values of that brand.

At the end of the day, good design is good design. That’s the easiest part — making something look good. But if there isn’t a consistent internal PoV and set of goals, you lack a reason why a design should be executed a certain way. That’s my job as a creative director — maintaining a connection to those foundational values and ongoing business goals to identify the “why.”

What do you look for when you’re building out a creative team?

Everyone has their own expertise, right? I'm not a general production expert. I'm not very good at logistics. Each person on the team should recognize their strengths and weaknesses so we can collaborate in a way that balances them out. That's the best thing about being part of a team — you’re able to lean on each other. Maybe a project we’re working on requires a design style I’m not really strong on, but someone else on the team is. I can provide direction and they can help me with production.

What are three things you can’t do your job without?

The most obvious one is Adobe Creative Cloud. That’s a must. I honestly love Creative Cloud, that you don to re-buy the package every year and can just have access to everything on a rolling basis.

Outside of the creative tools themselves, project management systems and tools have become really important to me. Asana is my favorite and what we ended up landing on at Playboy. I’ve tried everything from Monday to Basecamp to Trello, and none of them quite fit what I needed. As a visual person, I felt Monday wasn’t made for me. Asana made sense — kanban boards really help for every stage of a campaign’s production, from inception to the deck to selects.

We also used Google Drive on a company-wide basis at Playboy. It was our internal server and helpful for sending links out externally to all manner of partners. Those three tools — Adobe, Asana, and Drive — have been what I’ve used on a daily basis for years.

What’s a piece of advice someone once gave you that’s been influential to your career?

At one point, I was working for a small creative agency in my hometown. I got an offer from the Hef’s son to start a company with him that we’d build up and then pitch to Playboy. I wasn’t really sure about it. I had stability with my agency job at the time. It was a startup and it was in my hometown — I felt like I was part of something.

The founder of that agency, Chris Denny, has given me a ton of advice over the years. He’s probably my longest-standing mentor. So he and I went on a walk, and he said to me: “You should take the risk while you can. You’re not stuck here; you can always come back. If things don’t work out, we’ll have a job for you.”

What he said wasn’t really the advice I’m talking about, but the context of the relationship. It was a moment where I understood that work relationships don’t have to be a ladder-climbing, transactional thing. At that moment, I understood the true value of mentor-type relationships to the future of my career.

Building strong relationships with mentor figures in your career enables you to take risks, both in a creative and business sense. You lean on these people not only for advice, but for a push forward and a helping hand when you need it.

The advice he gave me was to take that risk, even if it’s scary. Him framing it that way — supporting me — made me realize that not taking the risk was a scarier idea than taking it. That’s something that’s stuck with me — whether I’m at a crossroads in my career or just on some project, if I feel like it’ll be a missed opportunity to play a safe game instead of taking a clear risk, it’s probably a good idea to take the risk.