How I Work: Skip Wilson, VP, Brand Marketing, Shutterstock
Skip Wilson is an expert generalist. Image: Skip Wilson. Header image design: Barbara Cadorna.
Christopher Wilson’s nickname is Skip and it used to be Skippy. So he riffed on that and lived by the words, “spread the fun.” Today, that means spreading not only fun but joy in life and at his job as VP, Brand Marketing at Shutterstock. He leads the company through an important period of growth as it expands from a stock imagery company into a creative partner that bridges the gap between brand, design, and execution, and bringing stories to life. “If you don't adapt, you don’t survive,” he says. “And our role at Shutterstock is to help our customers, our clients and the industry thrive, and we do that through our innovation.”
Here, the Seattle-based Wilson shares how he spends his days. It includes waking early to sync up with East Coast hour, why his dream studio focuses more on people than a specific place, and details about that one time he tried to convince his college buddies from Tennessee to homestead in Alaska.
Rise and Shine
I am based in Seattle, and most of my team sits on the East Coast, so my days start relatively early. Often, I’m in a meeting before I’ve had a chance to do what’s stereotypically expected of a morning routine, such as have a cup of coffee. But these meetings are an important moment to check in on my team, to ensure they have the clarity and tools they need to drive the ship on any given day. A huge part of my day is about coaching and mentoring others, while also leaving time for my own personal development. Otherwise, I follow the typical start to most people’s days, checking emails and Slacks before diving in.
Work Uniform
I’ve worked across entertainment, fashion, and technology, and I think there is always value in dressing the part. How you show up on camera or in person showcases a level of confidence. That doesn't mean that I need to have a suit and tie on to be believable. It just means that if I’m going to try to sell you on a creative off-the-wall concept, I should demonstrate that. I try as much as I can to not have a break or disconnect between what I’m espousing and my appearance. So, on camera, I will always try to be a little bit fly. But what you don't see is that I’m in sweatpants and soccer shorts just as often.
How I Structure My Day
The evolution of remote work can lead to constant meetings from 8 a.m. to 6 p.m. And those meetings, albeit valuable, may not allow people to protect their time so that they can produce. And in the creative industry, that is so important. So, I schedule my mornings for catching up with the teams and for meetings, and I have an actual dedicated lunchtime that’s not interrupted. Then in the afternoon when the East Coast team is signing off, I get to spend two hours working on individual tasks, whether those are emails or content creation. That, to me, allows for a healthy balance of at-work time and off-work time which is extremely important. I would encourage anyone to protect their time, and I do think having that level of structure allows you the comfort to step away.
Playlist Favorites
I have a music degree. I play clarinet and saxophone, which was my undergraduate education. My family is what we call ‘The Below Rent Jackson Five’ because my father, brother and uncles all play an instrument, and we’re all very musical. My brother is a DJ in Atlanta and my father also has a jazz radio show. I will often tap into them for playlist recommendations. Other than that, I’m listening to a variety of different things, whether it’s top 40, or NPR. I’m a big NPR nerd, I like the chatter and to learn passively what's going on in the world. I’m also based in Seattle, and we have a great radio station called KEXP that keeps you in the know of up-and-coming artists or artists you haven’t necessarily heard of. I think KEXP is the hometown hero here in Seattle in terms of music evolution for me.
Tools of the Trade
Shutterstock has gone through an evolution, and we're moving firmly into our next chapter. In any transformative environment, the shifts from how you have done business to how you should do business is where you find the most opportunity. I firmly believe in strategy, then structure, then execution. That’s the process and playbook that I aim to run. I always say to my team, let’s align on where we want to be within the year, even within the quarter, even within the month, and then we build the roadmap of how to get there. From there, transparency and communication as a process becomes critical to you moving, because when we move, we hope to move together. This isn’t as simple as saying, “Yeah, we use X tool or Y platform.” I think the playbook has to be: align on your company goals, figure out the roadmap to get there, and make sure that the people executing have the tools, the processes, the procedures and the room to move.
That’s where Shutterstock is right now. When you start seeing the successes that that playbook can have, it becomes easier. I would point to Generative AI as one of the most recent successes for Shutterstock in having a roadmap and a playbook as a success point. We really started off with external communications of our stance on generative AI and laying out a roadmap for how we intended to deliver on this before officially launching the product. This was followed by bringing experts and partners at SXSW to discuss the current lay of the land and its challenges. Next up will be our generative AI showcase to evangelize this work even further to the masses. There is a very strategic plan that makes sense and is intuitive. So, when we do what we should be doing, we reach that success. That success is what should propel that next execution. When you have a number of those wins and executions, that's when you start to have a repeatable process. For me, a solid playbook is one of the greatest tools you can have in our industry.
Dream Studio
My dream studio starts with the people. To create a place where true innovation, creative expression and business acumen are all possible, we must prioritize diversity, respect, trust, and vulnerability. I look to develop teams where there is a shared value and goal, where everyone is comfortable pitching an idea to the head of the company and believes in the work they are doing. Beyond that, this is a place where diversity of thought, experience, and skills are prioritized. And we must all have an understanding that we’re a business that has targets to meet and where performance is paramount. For me, the perfect brand studio is a place where there’s a bit of creativity, there’s a bit of business performance, there’s a bit of joy, there’s a bit of reflection, and hopefully a lot of success.
One Unique Thing About My Work Process
As a leader, I call myself an expert generalist or master of the miscellaneous. But I’ve had to develop dynamic chops. One minute, I will be having a conversation about headlines and subheads, and then the next I need to go into financial performance and budgeting. I think as a marketer and a leader, you have to have comfort for switching lanes and the confidence that allows your voice to be respected in a room. No longer is it acceptable for us to be purely analytical or purely creative. That is what my day to day looks like. I have that comfort because I’ve been thrust into that environment. I encourage the young leaders on my team to take that opportunity and spend some time where you have discomfort so that you can grow.
Mantra
My nickname is Skip and it used to be Skippy. My mantra was an old Skippy peanut butter saying which was “Spread the fun.” I believe when you have perspective on things, most things are just not that serious. There are people going through really serious things. The fact that we have jobs, we have roles, even when they're difficult — it can always be worse, and someone is always looking to be where you are. As much as possible, I want to live a full life, and a full life outside of work. I want to invest in family, in experiences, in growth, and for me that really is about spreading not only fun but joy.
My Bright Idea that Never Saw the Light of Day
In college, I read a story about this township in Alaska that was giving away land for free — all you had to do was get there. I was going to school in Nashville, Tennessee at the time and I reached out to my friends saying, “We’ve got to get to Alaska! This town is going to be the Cabo of 2025!” We never ended up going because we were poor college kids, but I still think to have that land there would have been a smart investment.
To-Do List Item That Keeps Me Up At Night
I have always been career-focused, and I’ve moved around several times to accommodate that career. Obviously, the pandemic has changed many of our preferences, and what we prioritize in life. So, my thoughts are often dealing with aging parents and my family spread across the U.S. which has me thinking, “Am I spending enough time on the things that are really important?” And that’s family, people, relationships and experiences. Conversely, in a very demanding professional role, I ask myself, “Are we prioritizing the right thing? What’s the mood of the team? Am I being the best leader I can be to empower the team to move?” So, I spend a lot of time worrying about the health of the team professionally, but the same is true of whether I’m spending the time contributing to my friends and family in a meaningful way.
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