It started with a LinkedIn message and a one-word subject line: “Shopify?”
I had just moved from Ireland to Vancouver. Before that, I led a research team at a gambling and gaming company. It was an interesting place to work, and a great way to try to understand human motivation. People make many irrational choices, but it’s amplified in gambling which makes it fascinating to study. Ultimately, though, I didn’t want to work for a gambling company forever. I decided to leave my job and my home country and try my luck in Canada.
“Ecommerce and gaming background,” read the LinkedIn message from one of Shopify’s co-founders. “Interesting. Would you come talk to us?”
I looked up Shopify, and the first thing I saw was an article that said, “Is this Canada’s smartest company?” The article outlined that Shopify was open to change, took non-conformist approaches to solving problems, and hired for potential. It sounded a bit idealistic to me, and my first instinct was to say no. I’d just settled in Vancouver; I didn’t want to move again to work for an Ottawa-headquartered company across the country. But the team was persistent, and eventually they convinced me to fly in to Ottawa for a visit.
I arrived on Cyber Monday, the biggest online shopping day of the year. The office was full of pure energy and excitement. People were up and about, laughing, and working hard. Despite the fast pace of the day, they had lots of questions for me. Everyone was interested in what my background had taught me about human psychology and motivation, and curious about how it could apply to commerce. It was enough to make me decide to join the User Experience (UX) team as Shopify’s first researcher, under one condition: I would remain in Vancouver and become one of the company’s first remote employees.
My role was to help Shopify understand who we were building for, and how good of a job we were doing. During my first couple of weeks, I was brought into a project that was fairly close to launching. As a researcher, there wasn’t much I could do at that point beyond giving a risk assessment of how people would understand the product, so I said, “I know you want me to work on this, but I think I can have more impact somewhere else. Do you mind if I try to find where I could be more useful?”
The answer was yes. Instead of working on a nearly completed project, I ran diary studies with merchants where I asked them to tell me about their experiences using the product, I listened in on support calls, and I learned firsthand how our users felt about Shopify.
Ever since then, I’ve encouraged people on my team to do the same. If you don’t think you’re working on the most important thing, you have to put your hand up. Treat it like it’s your own company. Today, six years later, I still feel that same ownership from myself and those around me. I work with people who care deeply about the problems they’re solving, and I care deeply too.
I care about understanding the challenges our merchants face, and evolving our products to address them. I’ve solved many problems in my time here, and there are others that I’ve thought about for six years and still haven’t figured out. It’s maddeningly motivating.
I call this feeling positive discontent. It’s counterintuitive to think that this kind of emotion could be a good thing, but let me explain. We spend a lot of time thinking about how to improve our products — particularly in the UX organization where our entire job is to make life better for entrepreneurs. People use our software to run complex businesses in complex environments. It’s not easy. So understanding how to create progress in our product, and maintaining positive discontent, is a real skill.
I often ask people, “What are you mad about right now?” If they don’t have anything to tell me, I’m worried. There are plenty of things we can do better. Maintaining positive discontent is a constant battle, but it’s a good tension for a successful company to have.
“Keeping a close connection to our users is one of the surest ways I know to build empathy for them, and gain a deep understanding of our products and the problems they solve.”
Even today as a senior leader, I spend a lot of time with our merchants. It’s the best part of my job. Keeping a close connection to our users is one of the surest ways I know to build empathy for them, and gain a deep understanding of our products and the problems they solve.
You never know what you’ll uncover when you visit a business owner, but you can be sure of one thing: they will tell you what they really think about Shopify. In my mind, you have to be willing to leave your desk and be accountable, face to face, with the people you build for. Entrepreneurs are the ones who work hard every day, who push their industries forward, who make themselves successful — and we help remove the barriers along the way.
Not only do we care about the entrepreneurs we serve, we also care deeply about one another. We work hard together, and encourage each other to grow as professionals.
The challenges we take on at Shopify are not for everyone. They require more effort than some people are prepared to give. But the reason I’m still here after six years isn’t because it’s easy. I’m here because it’s hard. I’m still learning every day. This is true for people across the company. To be successful here, you need to have a constant curiosity, be a continual learner, and have a level of humility to know that there is always more to find out.
We don’t hire leaders because they’ve done something elsewhere that we want them to replicate. Instead, we recognize their achievements, we look for their continued appetite for change and learning, and we want them to apply all of that to our unique set of challenges.
The possibilities here are infinite. It’s counter to the way a lot of other companies operate — if you work at an agency, your creative director often has to leave for you to advance into a leadership role. But here, that’s not the way it works. I don’t have to leave the company for a new VP of UX to arrive. We actively create opportunities for people. If you can make a difference here, and you care deeply about the problems you are solving, opportunities will come your way that are guaranteed to be outside of your comfort zone.
“If you can make a difference here, and you care deeply about the problems you are solving, opportunities will come your way that are guaranteed to be outside of your comfort zone.”