Cynthia is head of UX at Shopify, and co-author of Tragic Design (O’Reilly). She has a knack for solving complex problems from a business and human lens. Her range of experience has brought her broad recognition as a leading expert in ecommerce and UX. In addition to her day job, Cynthia is regularly invited to speak at events around the world, where her approach both startles and captivates. She is very comfortable with people mispronouncing her name and recently learned how to keep plants alive.

How has COVID-19 affected Shopify?

First of all, it’s affected our merchants, obviously, because they were impacted by a lot of the restrictions imposed by the pandemic. So a lot of them had to close their retail store, a lot of them had to completely change how they operated. We were very fortunate to see how scrappy and creative they were, at changing their organizations completely–and sometimes even their business model.

When our merchants change their behaviors, it affects our roadmap because we build things for our merchants. So if their priorities change, we have to adapt our roadmaps to meet their needs. In some cases, there were things already on our roadmap that became way more urgent. In other cases, we needed to build something from the ground up that would serve a very specific need.

COVID also had a deep impact on the employees at Shopify because we announced very early that we would be all working from home during the pandemic before many other companies had. Initially it was a temporary measure, but then in May we announced we would permanently become a digital by design organization. The leadership team decided to take the lead and try to design what a remote organization should look like, including designing the employee experience.


What kind of changes has this lead Shopify UX to make in operations and hiring that are here to stay? Are there any things that you’re going to lose because of that process?

We compare our employee experience with the very best in the world. We used to work in the most amazing offices. We had a team of architects thinking about every single room in the office to make sure that it met our needs, that it was beautiful, that it was inspiring, that it made you feel good. So when you compare the experience of working in that office with working at home in your home office–during a world pandemic where you’re not allowed to go out and get your food, and you might even be working with your kids with you–of course we’re comparing the pinnacle of the work experience with something close to the worst remote experience.

What we hope is that, as the situation progresses and eventually life finds a new normalcy, we will design a remote experience as good as the office experience was, but different. It requires a lot of investment in tools, technology, and infrastructure, but these are things that we can do and that we will do. We will design that experience the same way that the office experience has been designed in the past.

We’re going to lose things and we’re going to gain things, but our hope is that we will win more than we’ll lose. And this is something we’re already seeing.

What the remote experience enables us to do from a hiring standpoint is, first of all, to expand our search scope. We can now hire people outside of our core geographies, and we can give a lot more freedom for all areas of the business to define how and where they should hire their employees. These teams might have different needs. Some teams might only need to work in a similar time zone. In that case, every time zone is quite large, and includes potentially many countries. For some other groups or product lines, they can hire literally anywhere in the world because they are already working in an asynchronous manner.

So just having access to a lot more people means we can raise the bar even higher for what we consider excellence, which is amazing! We’ve always met people that wanted to join Shopify in the past, but they weren’t willing to move their life to one of our core locations. Now is a new opportunity for them to finally work with us and we’ve had a lot of them join.


In this new normal, what are some of the most important skills or emerging skills that will help people thrive?

Shopify has always hired people based on their adaptability. It’s one of our values. You have to thrive on change. In the past we’ve systematically asked people to adapt to new situations, to go through team changes, or to work on new projects. So the pandemic was just another change, but we were already staffed with amazing employees that are all showing signs of incredible adaptability and resilience.

Something that people have definitely doubled down on is their communication skills. You get a lot for free by having people sitting next to you. There’s a lot of context sharing that happens magically–you see the other person’s screen and you have a sense of what they’re doing. This does not exist anymore. So you have to adapt how you are communicating about your day, about your objectives, about your deliverables.

I think another important skill is the ability to trust another person and to not project your own insecurities. When you’re not face-to-face with someone, you have to trust that they are good at their job and that they are in it for the right reasons and they’ve been assessed for their skill. Some people have more difficulty trusting others, and this will definitely be an issue in a remote world.

Likewise, empathy is definitely something that UXers have always been really good at showing. But in this case, it’s even more important when we see some employees are juggling, full-time family responsibilities with full-time work. It requires a lot of empathy from the rest of the team to not feel like they’re shouldering their work unfairly. And thankfully, we haven’t seen people lacking empathy so far, but it’s going to become an even more important criteria when we add new employees to the team.


Since the pandemic hit, what has been one of your biggest learnings and how will this help you prepare for the future?

I have 2 kids at home, a one-year-old and a four-year-old. Obviously, I had to teach him many things during the past six months because I was suddenly promoted to a teacher role. I’ve always known that this was a discipline, that teachers are taught to teach — both my parents are teachers. But I had to start thinking about “How do I incentivize someone to learn, how do I teach in a way that it’s fun, that it integrates with the rest of his life and his own objectives?” My son has objectives that I don’t share! This made me realize how teaching is now more important than ever. We have a lot of people that are spread across the globe, and we want them to learn certain skills that we believe are important at Shopify.

So I’m really looking at our UX Operation team, for example–how can we create more learning opportunities and how can we incentivize people to learn in a way that it meets their own objectives? How can we teach in a way that is actually helpful? Not everyone wants to learn the same things, at the same speed, at the same time. For me, it was a stark realization that learning is the way we grow our culture. It’s how we increase the quality of our work. It’s not just by hiring more people, it’s by teaching people on the team as well.

How do you hope the UX team at Shopify will have evolved a year from now? What changes do you hope to see?

So I’ve already seen a lot of team members taking ownership of improving the processes to work more effectively remotely. People are jumping in and looking at our design tools and UX processes. They are proposing solutions and testing out new apps. I find that really fascinating and very encouraging. And it brings me back to what I was saying earlier: that the amazing work experience that we had before was designed, it didn’t happen by magic.

We have this new opportunity to design that remote experience and designers, by definition, are good at looking at a problem and trying to make sense out of it. I want the UX team to embrace that uncertainty and propose solutions, be part of making our company as great as it was before and even better. And then lead the way, show other companies that this is possible, and that it is a viable, sustainable way of working. There’s so much that comes out of working from home, we just haven’t done a good job of highlighting these things. I spend so much more time with my partner and with my kids, I take walks and I’ve been gardening, which would have been impossible before!

I’ve been taking care of plants at home, which brings me a lot of joy. I can start dinner at four o’clock, take a meeting, and then dinner comes out of the oven before I even get my kids from daycare. This is frankly amazing and maybe the only way we can achieve the mythical “work-life balance”.

Be Kaler Pilgrim


Office 1.6, 1st floor
2-7 Clerkenwell Green

UK +44 (0)203 319 4720

Contact us

Drop us an email and we will be in touch shortly.

Get In Touch

Send us your details and the relevant person will come back to you.
  • This field is for validation purposes and should be left unchanged.

Newsletter Subscription

Welcome to Futureheads. We’ll help you get ahead.

You can unsubscribe at any time at a click of a button using the unsubscribe link in our emails.