January 21st 2020
Stewart (@stewartsc) grew up in Scotland doing regular creative kid things: reading lots, drawing lots, making up stories. But unlike a lot of creatives who'd often much prefer to do the work rather than lead it, he's quite clearly a strategist and leader. It's in the way he thinks, the way he talks. It comes out in small ways, like in our chat when he'd mention not putting too much weight in job postings or how he liked to push people and brands to supersede their perceived boundaries. He's done that with his career too, having graduated before ever working with a computer and now leading teams making things on the internet. Stewart was at home in Portland when we chatted, a welcome interlude to my quiet morning.
What do you do?
I lead the Brand Design function on the Loom design team. Generally we’re thinking about how the company shows up in the world, how people find us, and when they do, what we want to tell them about the Loom product. We also think about how we might connect with someone who may want to come and work with us at Loom. So it has a big recruitment aspect to it. We’re charged with designing loom.com, and do a lot of video, photography, illustration etc, so we’re just thinking about how the company shows up in the world in all kinds of different ways. Like what’s our editorial strategy, all of that type of stuff.
In and out of that role, I like to push work as far as possible. I try to push people and teams and companies outside of their comfort zone a little bit and try to use that as a force and function for them to look at themselves and ask some critical questions of who we want to be and how we want to show up in the world. I love to experiment with that and push everything into a little bit of a new space.
The other thing I love is the people side. I love working with designers and writers and other creatives and being able to manage and mentor folks that may be a little bit earlier in their careers and hopefully help them get better at what they do.
How did that come about? Where did things start for you?
I used to draw a lot. I used to read a lot. I used to make up stories and write movie plots and that kind of thing. Back then, I was not even aware that that was ever a career option. It was either going to be you’re an artist and that didn’t seem like a particularly safe or stable career choice. Or there was something which was more traditional like architecture or some kind of technical type of job that had some sort of creative or artistic aspect to it. It wasn’t until I was looking to go to college that I realized there was even such a thing as a graphic designer or any of those types of things.
So I think, yeah you’re creative and you do these things when you’re a kid just because you want to do them and it makes you happy and it’s only later that you realize OH! That might actually be some job right there. I was terrible at math, I was terrible at chemistry and all that other stuff so I was glad that I figured that out.
It’s interesting to look back and see how each thing led into the other and really kind of organically came to be. I’m old enough to have graduated design school without ever having worked on a computer. Everything was done by hand. So that took me to a graphic design job. Then I ended up at Nike working on product, apparel product actually. Then, the sport aspect of that led me to Coca Cola because they were doing a lot of marketing around basketball and that’s where I started doing digital work. And because I started doing that digital work that took me to the next thing at CNN.
The last role that I had before joining Loom was at Intercom as a brand and design leader, building a team, and helping to define how that company showed up in the world and the market. And so that coming to where I am now made sense.
You’re right, it does all seem to line up, looking back. But did you ever have a plan? How did you seamlessly transition between all these jobs?
So for me, it’s been more that I’ve always kept on top of who are the people doing interesting things, who are the companies on my radar, the people I might want to work with, which is almost, I guess, the biggest thing because I think what’s happened a lot of times is I’ve known people when I’m in one job and they’re doing something else and then both go on and do other things and then at some other point, we actually kind of realize that we’re looking for the same things, then we end up working together.
In the last few years, as I was moving more fully into digital, I was going into those roles not because of the digital experience I’ve had but because I’ve had more brand strategy and marketing skills. And then there was new stuff to learn in those more digitally focused roles. I’ve always kind of like gone in and looked for opportunities which allowed me to lean into the expertise I have but also having room to learn new things. But it’s always been relatively organic, outside of looking to connect with the people I look up to.
How have you chosen which opportunities to pursue?
I remember when I was at Nike that I was a bit worried about being pigeonholed as a sports designer. That’s definitely a thing, a lot of people, they kind of move around from sports company to sports company. They go from Nike to Adidas to Puma and are always thinking, well, what’s next?
And I was always conscious about not getting into that type of cycle. I very purposefully looked for opportunities to join different types of companies that did a broader section of work, which would allow me some room to try new things and branch out a little bit.
The ideal scenario for me has always been that I don’t always want to necessarily change companies every time I want to learn something new, so where are the places that are doing different things and are growing in a way that allow me to grow with them? Or they’re doing enough different things that allow me to get involved in a bunch of different stuff?
When I started at Intercom, there were 100-something people. It was a decent size for an early stage startup but it’s still a smaller company than I had ever been at before. That was a conscious decision and something that I wanted to do, to see how it worked on the other side.
You’ve worked at a range of companies, both large and small. Can you talk a bit about the differences between the two in terms of culture?
I had a lot more autonomy at the startup size, but at the same time, some of the building blocks that you take for granted at a bigger company, like process and HR, some of these things aren’t always in place. You have to give something else up to get that autonomy. So it’s always this push and pull.
I don’t think there’s anywhere perfect that doesn’t have some kind of growing pains. It’s just about having your eyes open and thinking critically about what some of the pain points might be and whether those are worth dealing with to get the other stuff.
I’ve come to an interesting place regarding culture in that a culture that’s rigid can be tough for some people, and if you’re a good fit for that then wonderful but if you sit somewhere outside of that, it can be pretty tough.
I think the best situation are the companies that have a strong idea of who they are and who they want to be but they’re also flexible enough to know that as they grow and as new people come in, they’re all going to bring their own experiences and that’s going to inevitably result in the culture changing or morphing.
Some of the bigger companies that I’ve been at, the culture has been at a more solid state and it hasn’t been as fluid. And I think having room to adapt and grow and help influence the culture of a team and company with people and the other people you bring in, is the ideal situation.
You wrote a children’s book on creativity. How did that come about?
So the book was an interesting thing. It was something that we always wanted to do. It’s kind of a funny story. When my wife and I got married, which was nearly 12 years ago, we got married in Portland. We didn’t live here at the time and we needed a photographer for our wedding. So we went on Craigslist and found somebody and he shot our wedding for a couple hundred bucks and dinner. We kept in touch with him.
He became an entrepreneur and built a company called Circle, which they sold to Disney, and then he launched this new company which is a series of books based around conversations with your kids that may be difficult to have or start. I ended up doing a bit of consulting with them as they were starting to launch their company and they needed a little bit of input on what the design might be, what’s a way they can do it and what’s a way that’s fun but also easy to read and might be engaging for adults and kids. I gave some design and creative input and from there it was oh! you have some interesting ideas on the creative process, would you be interested in doing something? So they asked us to write a book, and that was super fun.
It’s just kind of funny how these things lead into one another.
What do you think is the key to building an agile career like you have and having that work positively for you during the job hunt process?
Stay open, stay flexible. Be curious about whose doing what and why and how. That will always open ideas and pathways that you hadn’t necessarily considered previously. And allow yourself to be guided by that. Being open and receptive of where technology and creativity and culture are moving is ultimately a better idea than trying to have a plan and rigorously sticking to it no matter what.
I’m really conscious of technology and how fast the industry movies and with that, there’s always going to be new stuff to learn. Culture moves much faster than companies do so there’s always things that you’re going to be looking at and thinking, oh that’s interesting. I’m always looking for new outlets and new things to try, whether it’s platforms or techniques or different ways of talking about yourself or your company and staying on top of that is something that I really love to do.
You’ll always go into new jobs with a set of skills and experience that are valuable and that’s why they’ve hired you, but they might not match up exactly to whatever they’re doing then at that moment, and so the types of questions I’ve always asked when talking to somebody new is what are the things you’re trying to do and what are the goals that you have for the team or the company? What are some of the roadblocks that are in the way between that and the successful outcome? And then thinking how might I be able to bring some of my skills and experience to help get you there. Trying to get some kind of idea of what a longer term view might be, that has always allowed me to think about how then can I use my experience as we go through that journey together.
So it’s never about what is the job description today, as it’s written. It’s always about more what’s the longer term plan and how can I help solve some of the problems that you might see between now and then wherever that successful outcome might be.
It seems like you approach things from a strategic angle, when it comes to your career. How has that mindset played out in your work?
A lot of times, you might see a specific job posting with specific language and wonder how you fit into that. But know that the idea the hiring manager has in mind is based on their own particular pain points at that time and the role will likely necessarily evolve over time. So even if you don’t check off every box on the application, there’s likely a lot of skills and experience you can bring that a company might not have in mind from the outset.
Maybe they’re looking for a designer but do they have their brand strategy in place? Or their messaging or they might be thinking a little further out about their content strategy. The job as it’s posted and as it’s written is somebody’s idea of how they might solve a specific problem as it stands right now but it doesn’t necessarily speak to how it interacts with the rest of the company and how that role might evolve over time.
Especially if you’re joining a smaller startup that’s growing, it will feel like a completely new company every six months. So you have to be aware that the job that you’re walking into on day one is going to be something completely different six months later.
And it’s probably good to get some idea of what the change might look like before you walk in the door.
-As told to Ana Wang, November 2019. Transcribed and edited for clarity.
This interview is part of our Work in Progress series, a raw and real look at modern dream jobs, the often winding paths of career journeys and the job hunt process, as we explore the questions: what does it take to build a successful career as a creative? How does the marriage of creativity and employment work together? What does the path to fulfillment at work really look like?
We’re looking to share more stories of people employed in roles and jobs in creative industries - technology, design, art - around the world. Email [email protected] and tell us a bit about yourself and what you do.