What led you into design?
I can’t reverse engineer my childhood and tell you a romantic story of how I ended up in design. Those who have known me for most of my life would tell you it is both fitting and yet completely random that I ended up in this field. Sure, did I make project tri-folds for my book reports that were perfectly mounted? Yes. Did I think I was going to become the next Nan Goldin after middle school photography? Who didn’t!? But look, I grew up in a family of Croatian immigrants whose primary concern was that I (1) get good grades so that I can (2) go to college in order to (3) get a job to provide for myself. My family were all small business owners running a painting business, a pickle plant, and a restaurant. It is hilarious that when you ask most tech designers, they’d happily choose any of those as alternative career paths.
There were a few basic principles in my house: work hard, help others, be aware of the world around you (60 Minutes was a staple program at my house) and most importantly, use common sense. This led me to believe that I might one day work in the foreign service (probably too much 60 Minutes)…Then I went to college.
I was on track to graduate in international studies and political science when I met a friend in class who had the most bizarre homework. One night she was designing a book cover, and the next an egg carton only using e-flute cardboard and no adhesive. After giving her unsolicited critique (something you can always count on me for) she suggested I try myself. In the spring of my sophomore year, I took a design course and it was after the first day of class that my entire trajectory shifted.
It was after the first day of class that I learned design was a career. I learned there were people who called themselves designers, who like me, were displeased with the world around them and wanted to create something better (now to explain this to my parents...still a work in progress). It all became clear when I was lucky enough to be offered the opportunity to intern at Facebook in 2012 at a pivotal time for the company. Katie Aronowitz was leading a team full of heavy hitters like Wilson Minor, Rasmus Anderson, Luke Woods, Mike Matas, Nicholas Felton, Koen Bok, Joey Flynn and many more. Every day my mind was blown by what these people were creating, it felt like magic. From that moment forward, I’ve been on a journey to create things that could make people feel the same way.
What does a typical day look like?
Most mornings I wake up, one eye open to check my phone, noticing I’m up 2 to 3 minutes before my 5:30 alarm. Let me assure you what follows does not include a run, an oil pull or transcendental meditation. No, most mornings, it’s a blind grab for a favourite sweater, a pair of comfortable pants and a scuttle down the stairs to press the brew button on the coffee pot my partner lovingly set up for me the night prior. I live in Seattle and choose to keep east coast hours to connect with my team who are located around the world. I do my best to greet my colleagues full of energy for my first meetings of the day but it is often when the camera turns on, I get my first look at myself and immediately regret not running a brush through my hair at least once. While this might not sound like the morning of someone who has a high degree of ambition in life, the scrappy nature of my mornings quite suits my working style.
At the start of this year, Shopify did away with most recurring meetings, meaning how I spend my day is a lovely mix of solo working time and smaller ad hoc discussions with colleagues about ongoing work. On a given day I might review several pieces of design work one on one or in a small group, discuss strategic trade-offs with my cross-functional partners about our most pressing challenges in the product, then take time to dive into a design challenge that I’m obsessing over. It’s this balance in my day that brings me a ton of satisfaction in my work.
What's your workstation setup?
My workstation is rather unremarkable, the only thing leaving a mark is the collection of coffee rings from the various mugs that have amassed at my desk. Perhaps the most important part is the numerous things I fidget with while on calls: a level, a tailor's measure, and my AirPods cases.
Where do you go to get inspired?
I go to work. It may sound like I'm simping for my employers but I’ve honestly had the great fortune of landing in teams where I’m surrounded by inspiring and talented people, who make me want to be better in every possible way. This is especially true right now at Shopify. The people I work with are an unbeatable mix of smart, creative, and motivated. They strike a lovely balance of deep passion for their work and a great sense of humor about this thing we do called building product.
When not getting inspired by all the great work my team does, I’m pretty basic when it comes to sources of inspiration. I spend more time than is possibly healthy on the internet, spelunking are.na, appreciating what people are creating and writing about. I studied graphic design and as such I still draw a huge amount of creative energy from seeing amazing work that other people are making.
When I get the chance, seeing art in person really fills my cup. There’s nothing quite like an artist's unwavering desire to create a thing that they will sacrifice everything for just to do it, even if no one else gets it…I love that, I could never do it and I appreciate it so, so much.
A show that has always stuck with me is a solo show from Hank Willis Thomas entitled WHAT WE ASK IS SIMPLE from 2018. Thomas had printed historical images of resistance on “retro-reflective” surfaces, meaning that to be seen fully they must be activated by a flash of light (or a pair of glasses you were given in the gallery). There were so many layers of depth to this show: shedding a light on centuries of protests against racial injustice, the desire to photograph every piece of art we see, exposing issues that are far deeper than the surface...too good.
What product have you recently seen that made you think this is great design?
I’ve got a few quick ones:
For all-out brain-busting, paradigm-shifting, craft-crushing design, I gotta give it up to the fine folks at The Browser Company for their work on Arc. No notes.
For their unrelenting sweating of details, major props to Luke and Daniel on Any Distance. I don’t even run. I am nearly sedentary, but this app is absolutely stunning.
For doing something new, watching Laurnet Del Rey play with new UI paradigms and just create out in the open has been an absolute pleasure. You can tell they're having a good time and that's probably what makes us all drawn to the work.
For most inspiring solo project out there right now, Marcus Eckert for his work on Riveo. If you have not downloaded this thing yet do so now. What he is able to achieve with shaders continues to bend my brain. It's an incredibly powerful video editor in the palm of your hands.
Lastly, for putting on one of the best events I’ve been to, a massive congrats to Cameron and Fiktive Kin for putting on Kinference last month. Highlights for me included talks from Paula Scher, David Rudnik, Gabe Whaley, Haraldur Thorleifsson, and Matt Hall
What pieces of work are you most proud of?
I fear (and I loathe that I’m making this comparison) that I’m a bit of an Adam Driver when it comes to my own design work: there is very little that I’ve done thus far that has hit the level of quality I aspire to create or be a part of creating. Maybe not a huge vote of confidence for the person reading this who thought they might want to work with me someday but I've got a high bar that seems to perpetually inch higher the closer I get to it.
There’s this thing…the total design of a thing, from its branding to its function to its overall impact on people, that I’ve never quite struck. The body of work that has come closest was my work at Artsy, where I had the opportunity to tackle a broad set of design challenges. From branding to exhibition design, designing software and hardware, to leading product, there wasn't a part of design and software development that I didn't get a chance to get my hands on.
Luckily, the work I am in the midst of at Shop stands a very good chance of giving me the opportunity to achieve that goal. Shop is a project that will necessitate total design if it is to be successful. And if it is successful, it will be in large part because of the team I have the honor of working with, which, in my anything but humble opinion, is the best in the business.
There is a smattering of things we have shipped in the past 6 months and even in the last 2 weeks that indicate to me that we are on a trajectory to do something truly special. Most recently we shipped shop.ai, an early experiment to begin understanding how AI-powered shopping might look. It is the first time in my career I created something that I really wanted to use. While "designing for yourself" runs counter to the ill-informed dogma that you aren’t your own user, it is one of the most satisfying feelings a designer can have. I’m convinced that when designers create things they actually want to use, they do so with much more care. If more of us designed this way we might have a more thoughtful internet.
What design challenges do you face at your company?
Platform thinking in a consumer experience
One of the interesting artifacts of working at an engineer founded SaaS-first company is how much we talk about platforms. Every aspect of what we build must be interoperable, portable, and fungible. Classic consumer-driven design tends to be far more opinionated about what is and isn’t mutable. Less is more, house the user in a "walled garden" etc…the Apple way. When I started working on Shop, I found platform thinking hard to square with trying to build a classic consumer app and many designers who join the team also find this challenging.
But thinking about Shop as a platform is now so obvious to me when you look at the ways we connect merchants and buyers; from their first touch on the online store by checking out with Shop pay, tracking their packages on the app, then discovering new brands they love, it's clear how Shop is really a network of experiences, a network that helps merchants achieve their goals and builds trust with buyers over the long term.
In order to effectively design that network, designers have to take a more object-oriented way of thinking about creating experiences. This is even more important as we are confronted with the opportunity to create new design paradigms that AI enables. Our biggest challenge now in Shop is reorienting our talented team of designers to think about shaping the future of consumer experiences in a less linear fashion.
Wading into the unknown with AI
This would be a terrible time as a designer to lean into what is often a healthy skepticism about technology. We are at an event horizon that only shows up maybe once in a career if you’re lucky. AI has created the opportunity to fundamentally challenge design paradigms we’ve become accustomed to over the past 15 years, particularly for consumer apps. This space is moving incredibly fast and much like the dawn of consumer computing and the internet, engineering is leading the way…how else do you think a chatbot has become the de facto interaction pattern?
History will repeat itself here.
We thought keyboards were king until the mouse and graphical user interface were introduced. Then, touch screens and skeuomorphic metaphors removed the keyboard and mouse and brought the rest of the world online (I credit the ipad with bringing my parents online). People could feel their way through discovering the power of the internet in part thanks to the native app ecosystem. Design was central to that evolution. When I think about how AI can be used to bring people closer to the information, people and experiences they desire, design has a massive role to play in shaping how this will function (Sam Altman recently doubled down on this same point.)
Yes, the move from imperative to declarative interfaces is inherently language-driven, which is incredibly powerful, no doubt. But I am hard pressed to think the only way to harness the power of AI is to have a chat assisted experience at every turn. Words spoken by a designer who just shipped a chat assisted shopping expereince I'm aware. My point is that this is just the start, not the end.
As designers, we have a huge opportunity to consider how AI can generate experiences that truly mold what users want. In some sense, you could argue we’ve been hamstrung for years by having to build products that we hope the broadest set of people understand. But how exciting and simultaneously terrifying is it to consider designing for a future where people get to declare what their interface is. This challenge or opportunity, depending on how you look at it, is what is consuming me at the moment.
Delivering today while defining tomorrow
I think this is a challenge every design team faces. How do we continue to improve experiences for the people who use our products week in and week out while driving towards an ambitious vision of the future? I know a team is well balanced when there is a good mix of what I refer to as high and low design happening on a weekly basis:
- Low design: Designers flying at a low altitude close to their team, shipping value to the people who use our products on a weekly cadence.
- High design: Designers flying at a high altitude, looking holistically at their product area, spotting new opportunities, developing a vision and most importantly seeing how the entire ecosystem is impacted and improved by decisions they are making.
When there is a never-ending list of short-term problems to fix, it can be challenging to find the space to ensure both are happening in parallel.
What music do you listen to while designing?
Any advice for ambitious designers?
Always be a chef, never a server
As you grow in your career, your stakeholders will become more challenging. This is a good thing. You will be working with smart, demanding decision-makers who will push your work. If you’re lucky, those decision-makers will have strong opinions about design. The mistake that I see being made again and again is a designer moving from being a chef: developing their designs with a strong point of view, inviting others to try the soup and provide feedback, and instead becoming a server, putting various designs on a platter and giving them to stakeholders who ordered them without much of an opinion about what is good or bad about them. Don’t do this. No one wants this from you. People want you to cook. They want a dish served with a point of view, and while they may argue it needs more or less salt, even the most demanding customer does not intend to join you in the kitchen (a cautionary tale from The Menu)
Design the desirable
Many will be familiar with the sweet spot for innovation popularized by IDEO in the early 00’s which is a great checklist for any product idea big or small:
- Desirability: Is this a thing people want?
- Feasibility: Can we build it?
- Viability: Can the business grow or sustain from this?
You can roughly assign these to roles in a cross functional group:
- Designers are responsible for making things desirable
- Engineers are responsible for determining the feasibility
- Product managers are responsible for assessing the viability
As designers become better at understanding technical constraints and how to positively impact the business, an odd thing can happen…they stop thinking about what people want. Ambitious designers want to be great cross-functional partners but sometimes that can cause them to be pulled into the realm of feasibility or viability, cutting off their creativity and they begin to pre-constrain their solutions without really knowing it. Try to recognize when you’re doing this. Even better, find great cross-functional partners who see your unique value as being the driver of defining what people desire and make them hold you accountable to it.
Demand intellectually rigorous discussions about your ideas and foster them with others
If you want to produce great work, you have to accept that people challenging you is a natural part of the process. Great work is done by teams where everyone takes a shared responsibility in kicking the tires on ideas that are put forward. This requires a shared understanding of the team's goals and where the product sits today, informed by data and insights. From there, no matter what team people work on or who they report to, everyone should take a shared responsibility in debating the merits of various solutions that are put forward.
I see two mistakes made in this area. The first is entrenchment, the person or team who is dug in about a specific idea who, when introduced to new information, will stay the course due to sunk cost fallacy or entrenched assumptions. Conviction is great, but if you’ve not tried to take the other side of a position you’re arguing, have you fully understood your idea? Then there is the dreaded groupthink: a group of people who are more worried about optimizing the process of a discussion rather than whether or not anything meaningful will be discussed. As Fran Lebowitz puts it, “polite conversation is rarely either” and while I don’t think having a rigorous discussion requires being an asshole, I worry that we’ve mistaken politeness for not saying anything at all and we’re not providing the critical feedback necessary to make work better.
Feedback and debate about ideas are such a gift to anyone looking to grow in their career. It helps improve everyone's understanding of how to best solve a problem and establishes shared expectations for what a 'good solution' will look like. If you're doing it right, it's probably slightly uncomfortable, but you should come away feeling enriched by what everyone has gained from the discussion. I’ve grown the most in these types of environments.
Pixels over post-its
No process you develop, design sprint you host, or principles you hold will ever be more important than just creating something, at any fidelity, with whatever tools you please. You might argue some of those rituals are inputs into high-quality work but don’t make it the thing you spend time intellectualizing about. The creative process, whether on your own or in a group, is messy and organic. We've wasted a bunch of energy over the past 10 years unintentionally sucking the creativity and imperfection of what we do as designers and rationalizing it to the point that I can’t recognize design portfolios anymore. No double diamond, post-it party, ‘design thinking’ exercise will beat a group of people bouncing ideas off one another, bringing those ideas to life to as high fidelity as is necessary to give those ideas a feeling.
A note for the truly ambitious
Find a team/company/project that allows for non-linear paths of growth. Don’t let organizations box you in. After only my second year in a full-time job I was thrust into management, 6 months later I became a product lead. Later, I would become the person who helped pitch partnerships to brands like BMW, spoke to our board, but also cut App Store screenshots and designed company swag. I have been so many different things, and 10 years later, I continue to be. With each passing year, I would have career discussions where managers tell me I need to pick. Pick being an IC or a manager, pick leading product or design, pick being in the weeds or working at a higher altitude…Any of the roles I just listed would be a fine choice, so long as it's yours. If you're ambitious, if you truly like this thing that we call building product, and you like taking a scoop from many items in the buffet line, then find a place where you can load up your plate. Find a place that will celebrate that, not hinder it. I credit my growth as a designer in part to great mentors who have allowed me to be led by my curiosity about all the aspects of design and product development.
Anything you want to promote or plug?
We're very lucky to be growing the team at Shop. If you're interested in learning more about our open roles we'd love to chat with you.
I also want to take a moment to say thank you. Thank you to my family, my partner Maura, my friends, colleagues, and mentors who all support me in all ways big and small 🖤
(Full list of recent design tunes here)
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