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Creative Ops

Brooklinen’s Jess Gary on what changes as you move from designing to creative direction

May 03, 2023 · 5 min read

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 kind of creative director are you — what does the role entail?

As I see it, the role of a creative director is not just to tell people what to do. The best work comes out of collaboration, so I see myself more as a mentor and facilitator. My job is primarily to create a great creative work environment so the team can come up with good ideas and I can help move those ideas forward.

I had a bit of a winding road to the role. I studied art history and got a job at my university, HSU, working in the print shop, where I worked closely with the graphic designers, which originally piqued my interest. After graduating and working in the museum world for a bit, I enrolled in continuing ed, where I received some tactical training in graphic design. That led to a job at a very small fashion brand, where I just applied myself and worked really hard — a fake it ‘til you make it situation. I taught myself  how to shoot product photography, I was designing lookbooks, and soon enough I ended up at Barkbox.

Like many creative directors, I mostly figured it out as I went along. The major blessing was working in rapidly growing, fast-paced startup environments where I started as the only in-house creative and within a couple years built out a design and photo team. The only option in an environment like that was to learn fast, on my feet.

What are the most important traits and skills to look for when building a creative team?

Hard skills are definitely part of it, but more than anything, it’s about looking for people with the right approach and the right attitude. You can have the most talented creative ever, but if they're a jerk, not collaborative, and nobody wants to work with them, then you're not going to get very good results from the team. Look for people who are excited about the work, open to feedback, and eager to learn. Especially in the startup and tech world, you have to find people who are very adaptable. 

With Brooklinen specifically, in the five years I've been here, it’s become a completely different company every couple of years as we've scaled from 20 to over 160 people. That means people's roles sometimes shift, as does what we need from the team at large. So for someone to thrive here, we look for people who are creative, yes, but even more than that, highly adaptable and collaborative.

That pace of change is especially tough on a creative team. I’ve had the pleasure of coaching up some of our now director-level creatives through it. Personally, I entered this industry as a graphic designer and now the software I learned on has been replaced by new tools that I fumble my way through…but that’s not my job anymore. So that’s the key to coaching people up through these changes: they’re undergoing a transition from doing and executing to leading and mentoring.

If you love doing creative work, don’t push yourself into a management role. Be honest with yourself and be an incredible graphic designer, writer, or photographer. If you want to move into leadership, do it, but understand you’ll be moving away from creating. You have to be confident enough to not feel threatened when other people come in and start doing the job you were doing. You have to challenge yourself to figure out how you can serve the business in a new and different way.

What's the hardest part of shipping good creative work?

Bad results occur when there’s poor strategy and a lack of planning up front. Good briefs are the most important thing for a creative team to deliver great work. If the people writing the briefs and asking for the work haven't thought through the strategy or keep changing their minds, that means we won't have a clear picture of what the goals and objectives are. The creative is going to suffer because of that.

When you’re in the middle of the work, the challenge is maintaining clear and efficient collaboration and communication. I've seen this especially as a team grows and we're tackling more and more projects at once. People will cut out some of the time-consuming but really important work of just putting their heads together, checking in, and realigning. 

Digital tools are great but I think project management software should only be a way to track the work. There’s no replacement for actually talking and working together. Async feedback can become a circular game of telephone. Instead of the writer and designer just getting in a room together and figuring it out, we'll spin out in comment and feedback threads across various tools. As a creative leader, I then have to pull out the red flag and say, “Hey, no more commenting, just get in a room and figure this out.”

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

As much as we work in a digital world now, I still need my daily planner and paper. There's just something about putting my thoughts and to-do list in writing, physically on paper, that feels more tangible and permanent. At the end of every day, I review what I've accomplished that day and then physically write out my to-do list for the next day, so when I sit down at my desk in the morning, I'm ready to just jump right in. 

Space is key. To be creative, we need time, we need space. There's a reason why people say they have their best ideas in the shower or driving, just daydreaming. You have to give yourself time to do nothing, which is challenging in our productivity-obsessed world. 

The team is everything. I couldn’t do my job without having a really talented team around me. Great work comes from a great team, not an individual.

What piece of advice do you have for young creatives just starting out? 

Be curious about the business. Great creative doesn’t just look nice, it should solve a problem or communicate something to the audience. If you can make a case for how the creative you’re pitching solves a business need or helps the client reach a goal then you’ll have a much easier time pushing your ideas through. This is one reason I’ve built my career as an in-house creative. I love being immersed in the business, understanding the intricacies of how it operates, and using creative strategy to drive goals forward. It’s so rewarding to see the results of your work paying off.

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