Darrin Henein - The new bar for design excellence at Shopify

Summary

Detailed Summary of Dive Club Episode Featuring Darrin Henein – VP of Design at Shopify

Release Date: June 6, 2025
Host: Ridd
Episode Title: Darrin Henein - The New Bar for Design Excellence at Shopify

---

1. Introduction to Darrin Henein

In this episode of Dive Club, host Ridd interviews Darrin Henein, the Vice President of Design at Shopify. Darrin shares his extensive experience in design leadership, his journey to Shopify, and insights into how AI is transforming the design landscape within the company.

2. Journey to VP of Design at Shopify

Darrin’s path to becoming VP of Design was unconventional. Initially aspiring to be a doctor like his father, he transitioned to design through a series of serendipitous events:

• Early Interests and Transition:
  [01:28] “Growing up, I wanted to be a doctor... started making posters with Photoshop and discovered Geocities, which fascinated me with the ability to share creative ideas globally.”

• Freelance Beginnings and Startup Experience:
  [01:53] “Started a studio with a friend, took any freelance job available, and enjoyed the problem-solving aspect. This led him to a startup in Toronto and later to Mozilla, where he contributed to the Firefox web browser.”

• Joining Shopify:
  [02:51] “Moved to Shopify in early 2016 after connections from the community and prior experience, initially taking on individual craft roles before expanding into leadership.”

3. Realizing a Career in Design Leadership

Darrin recognized his potential in leadership as his career progressed:

• Transition from Individual Contributor to Leader:
  [03:41] “At startups and Mozilla, he started as an individual crafter but realized his impact could grow by mentoring and leading teams. Joining Shopify, his team eventually grew to over a hundred members.”

• Embracing Leadership Roles:
  [04:26] “Acknowledged the shift from individual contributions to fostering a team-oriented environment focused on excellence.”

4. AI in Shopify's Design Practice

AI plays a pivotal role in Shopify’s design strategy, enhancing productivity and innovation:

• AI as an Accelerant:
  [06:17] “AI tools accelerate the design process, allowing quicker ideation and higher-fidelity prototypes. Darrin emphasizes that AI doesn’t change the process but enhances it.”

• New Categories of Work Enabled by AI:
  [08:19] “AI allows for higher-fidelity work and democratizes design skills, enabling non-designers to contribute more effectively. This elevates the overall quality and sets higher standards for design excellence.”

5. Impact of AI Tools on Design Processes

AI integration has transformed how design teams operate at Shopify:

• Faster Prototyping and Evaluation:
  [07:35] “From idea to evaluable prototype happens much faster, allowing for rapid experimentation and refinement.”

• Enhanced Collaboration and Feedback:
  [08:19] “High-fidelity prototypes encourage broader team involvement, ensuring diverse input and reducing blind spots.”

6. Technical Proficiency and Design Skills

Darrin discusses the evolving skill set required for designers in an AI-augmented environment:

• Expectations of Modern Designers:
  [11:22] “Shopify values generalist designers who bring a broad set of tools and can leverage engineering talent. While traditional coding skills are no longer mandatory, understanding software development remains beneficial.”

• AI Tools Lowering Barriers:
  [12:03] “Designers can now use natural language to generate code prototypes, bridging the gap between design and development.”

7. Maintaining Alignment Amid Rapid Prototyping

With numerous AI-generated prototypes, maintaining team alignment is crucial:

• Vision and Strategy as Anchors:
  [13:13] “Despite the speed of AI tools, having a clear vision and strategic direction ensures that experimentation aligns with overarching goals.”

• Consistency in Product Quality:
  [13:13] “Designers must ensure that their work contributes to a cohesive and high-quality product, much like ensuring every app on the App Store adds value despite the ease of creation.”

8. Concrete Communication in Design (“Concrete Elephants”)

Effective communication is essential for synchronized team efforts:

• Concrete vs. Abstract Communication:
  [14:23] “Darrin emphasizes the importance of making ideas concrete to avoid misunderstandings. Referencing the elephant parable, he advocates for tangible visual examples to ensure everyone is aligned.”

• Reducing Ambiguity:
  [16:12] “Clear documentation and visual design documents minimize ambiguity, especially in remote or distributed teams.”

9. Design Critique and Feedback Culture

Fostering a safe and productive feedback environment is central to Shopify’s design culture:

• Creating a Safe Space:
  [19:35] “Design critique should focus on the work, not the individual, allowing for vulnerability and risk-taking without fear of judgment.”

• Constructive and Collaborative Feedback:
  [21:37] “Darrin models openness by acknowledging his uncertainties and encouraging team members to engage in dialogues about design decisions.”

10. Culture of Excellence and Leadership Principles

A relentless pursuit of excellence defines Shopify’s design culture:

• High Standards and Accountability:
  [09:13] “Shopify’s commitment to craft ensures that every contribution meets a high standard, fostering a culture where mediocrity is unacceptable.”

• Leading by Example:
  [24:26] “Darrin leverages his design experience to lead effectively, setting high personal standards and ensuring fairness in expectations.”

11. Balancing Craft and Outcome

Designers must navigate the balance between creative craft and practical outcomes:

• Outcome-Oriented Design:
  [25:51] “All design activities are geared towards improving the product for merchants, ensuring that creative efforts translate into tangible value.”

• Commitment to Final Product:
  [27:22] “From crafting prototypes to engaging with engineering teams, maintaining the integrity of design intentions is vital for successful product outcomes.”

12. Hardware Design at Shopify

Expanding into hardware presented unique challenges and learning opportunities for Shopify’s design team:

• Differences Between Software and Hardware Design:
  [31:04] “Hardware design involves considerations like material costs and the irreversible nature of production decisions, requiring more rigorous and methodical processes compared to software.”

• Integrating Design and Engineering:
  [31:47] “Leading both software and hardware design teams, Darrin ensured that every design decision accounted for practical constraints, maintaining high standards throughout the development process.”

13. Significant Achievements and Stories

Darrin highlights key milestones and successes during his tenure at Shopify:

• Winning a Red Dot Award:
  [34:27] “A proud moment was winning a Red Dot award for one of Shopify’s first hardware products. This recognition validated years of hard work and innovation within a small team.”

• Impact of Hack Days:
  [53:06] “Shopify’s hack days have been instrumental in spawning successful products like the Shop app (originally known as Arrive) and the Point of Sale (POS) system. These initiatives encourage bottom-up ideation and rapid prototyping, leading to impactful product developments.”

14. Advice for Aspiring Designers

Darrin offers valuable advice for those looking to excel in the design field:

• Embrace Curiosity and Continuous Learning:
  [45:11] “Maintain a problem-solving mindset focused on user needs. Treat design as a lifelong pursuit, constantly studying and mastering new skills.”

• Practice by Replicating and Analyzing:
  [46:30] “Copying and dissecting existing designs helps in understanding the rationale behind successful products. This practice builds foundational skills and sharpens design intuition.”

• Value of Original Thinking:
  [48:43] “Promising designers are those who think outside the box, offering unique perspectives rather than conforming to popular design trends.”

15. Final Thoughts

Darrin concludes by emphasizing the importance of ownership, collaboration, and maintaining high design standards to drive Shopify’s success. His journey exemplifies how passion, curiosity, and a commitment to excellence can lead to impactful leadership in the design industry.

---

Notable Quotes:

• “When that note was shared, it was cool to see the response because for us who know Toby, like, that was not a surprising note to see from him. It was kind of like, of course, like this is what we were doing already and what we're planning to do.” — Darrin Henein [06:17]

• “I want everyone to feel like they're on like the Bulls from the 90s, where, like, hey, everybody is pitching in 110%. Everybody's here to play hard, everybody's here to work hard. And there is a culture of excellence.” — Darrin Heneen [00:13]

• “Design is about solving problems for people. I think in most cases, if that remains true, you know, there's always work for us to do.” — Darrin Heneen [45:11]

• “Everybody can contribute to our strategy. Everybody can contribute to our roadmap. Everybody can propose things they think we should be doing.” — Darrin Heneen [03:37]

---

This comprehensive summary encapsulates the key discussions and insights from the episode, providing a clear and engaging overview for those who haven't listened to the conversation.

Transcript

[Darren Haneen]

There's no more excuses. You have these tools. You can just use English to talk to them.

[Rid]

Are there specific AI native behaviors that you're hoping to see more of as a leader who's trying to turn AI into a competitive advantage for Shopify?

[Darren Haneen]

I want everyone to feel like they're on like, the bulls from the 90s, where, like, hey, everybody is pitching in 110%. Everybody's here to play hard, everybody's here to work hard. And there is a culture of excellence.

[Rid]

In a world where you just have a ton of prototypes flying around, how do you ensure that teams at Shopify are able to stay aligned? Everything's moving at the speed of AI, and it's so easy to just crank out a bunch of different experiments in every direction.

[Darren Haneen]

Shopify is a company where the craft is king. And the quality of our product and the quality of Shopify is kind of the ultimate measure that we all hold ourselves accountable to. Everybody can contribute to our strategy. Everybody can contribute to our roadmap. Everybody can propose things they think we should be doing.

[Rid]

Welcome to Dive Club.

[Toby]

My name is Rid, and this is where designers never stop learning. This week's episode is with Darren Haneen, who's the vp, VP of Design at Shopify.

[Rid]

So we're going to do a deep.

[Toby]

Dive into how they work, including all of the different ways that AI has influenced the practice of design. And Darren also shares some interesting thoughts about what it looks like to make a strategic impact as a designer at Shopify.

[Rid]

But before we get into all of.

[Toby]

Those details, let's learn a little bit more about Darren and the journey that.

[Rid]

Led him to VP of Design.

[Darren Haneen]

It wasn't what I had planned initially. Growing up, wanted to be a doctor, following my father's footsteps. Have always been quite interested in the sciences. So I went to school, went to university in Toronto here for the hard sciences. Human biology, physics, chemistry. During that time, started taking kind of some odd jobs, doing posters and things like that. Got myself a copy of Photoshop. Just started making a few bucks here and there. And along the way, discovered geocities, as we can probably all remember.

[Rid]

Nice.

[Darren Haneen]

And was just fascinated by this idea of sitting in my dorm room making something on my laptop that anybody in the world could see and I could tell the story and I could share my kind of creative ideas and things like that. And in contrast, medicine does move, but more slowly, and I just have this, like, short attention span. I like new ideas, I like learning things. And quickly became attracted to this idea of like, hey, maybe this isn't the path for me and maybe design and especially designing for the web and then later for mobile and things like that might be more interesting. So I finished my degree, moved back to mom and dad's house and just started my own little studio with a friend from high school. He did all the business stuff, I did all the creative and dev and got some traction, started doing some, you know, a lot of freelance work. The principle was that I would take any job someone was willing to give me and then just figure out how to do it later. And I actually really enjoyed that problem solving kind of learning aspect of the early stage of my career. And from there hit a point pretty quickly after a couple of years where I realized I can learn so much on my own, but I want to be surrounded by people who are excellent. I want to be surrounded by people who are. Know the craft, who, who know how to build products and software. And so found myself at a startup in Toronto where I really kind of cut my teeth in proper software design. We were doing a lot of mobile apps at the time. This was pre iPhone, a lot of work for BlackBerry, Android, Windows Phone. So spent some time there, moved from there to Mozilla where I spent a couple years working on the Firefox web browser. Committed a lot of code to Firefox for iOS as kind of a design engineer, and then spent a couple years on their developer tools team. We ended up across the street in our office from where Shopify was opening their office in Toronto. And I had a few friends there just from the community who had been part of some acquisitions. And so it was in early 2016 that got a couple of calls and they pulled me over across the street and started my job there.

[Rid]

At what point did you realize that design leadership was the track for you? Like, how did you go from design engineer to now VP level at this massive company like Shopify?

[Darren Haneen]

I learned a little bit at the startup that I was at and then again at Mozilla. Both places I started in more of like an individual crafter role, but both are growing quickly. And I just kind of realized, okay, my limits here are a 40 hour week, give or take. And at a certain point, if I want to expand my impact beyond that, one way to do that is to take on a leadership role and to mentor others and to lead others and to bring a group of people around a common problem or solution and through that group see greater impact. And so when I joined Shopify, I was in that capacity. I think I had just one report on my first day and he sat right beside me and we kind of.

[Rid]

Went side by side.

[Darren Haneen]

And so I did end up doing a fair bit of individual work early in my time at Shopify. But over the years that team grew over a hundred at one point. I've just seen kind of like different shapes of leadership here as well over the nine years.

[Rid]

I don't know how intentional you said individual crafter, but I'm definitely saying that instead of individual contributor moving forward.

[Darren Haneen]

Yeah, I mean, I like the sound of it better than I like it a lot.

[Rid]

I like it a lot.

[Toby]

Real quick message and then we can.

[Rid]

Jump back into it.

[Toby]

If you're working at a startup right now, then I have some pretty good news for you because Framer just released an incredible offer that gives startups free access to their launch plan for a year. That's $900 to design and ship your site with Framer, which is a total no brainer. I mean, I even took advantage of the deal myself. So definitely don't miss out on this offer. You can head to framer.com startups to learn more. I've been designing for a long time, but somehow I only signed up for Maubin this year and honestly, I can't believe that it's taken me this long. Like it's literally a cheat code. Being able to find inspiration for basically any pattern, any product flow. It's fast, it's beautiful. And I already cannot imagine designing without Maubin. It's the first place that I look at for inspiration and I can't recommend it enough. So head to Dive Club Mobin to get started today. That's M O B B I n.

[Rid]

Okay, now on to the episode. All right, well, Darren, I can't have you on and not talk AI because Toby had his memo leak or whatever and obviously the entire tech world was talking about it for about 48 hours and. And Shopify is one of the first really big companies to have this type of AI forward stance and make it public. So how do you see that kind of mandate influencing the way that design is practiced at Shopify?

[Darren Haneen]

When that note was shared, it was cool to see the response because for us who know Toby, like, that was. It was not a surprising note to see from him. It was kind of like, of course, like this is what we were doing already and what we're planning to do. And that's just his mindset is to be kind of at the front of these things. I think there are a few responses. Like for me, one was having worked in design for two decades now, like, I've seen a lot of change in our tooling and what's available to us. And, you know, going way back to doing UI design in Photoshop was a pretty tedious, toilsome process. And then fireworks came along and you had styles, and then there was Sketch and Zeppelin and Envision and you could do feedback on the web. And now with figma, like, there's always been these tools, and for me, what they've allowed us to do is to not necessarily change our process, but just to move more quickly and to answer questions more quickly. One simple way to look at it with AI is that we now just have tools that accelerate that process even further. And so to go from an idea to something that you can evaluate is a lot faster. And the fidelity of what you're evaluating is also higher in that it's not a static prototype anymore. It's not even just a kind of a fake one. In figma that you're kind of clicking through static screens, you can actually build functional prototypes in just as little or less time. And for me, design has always been about solving problems. And so you're trying to find a solution, and on the path to that solution, you're just guessing a whole bunch. You're just, you're trying to find the optimal solution, but nobody knows what that is. And so in the past, you would do research, you would run studies, you do usability tests, because building that solution was quite expensive, took a lot of time, took engineering capacity, and once you kind of committed down a road, it was very hard to go back and change your mind. Whereas now that process happens in seconds in some cases. And so, so we can try more things and we can get to that solution, or we can get to something that we can evaluate much more quickly. And so in some ways it's just another tool that lets us do the same thing better. But I think there's also a whole category of work that's new and that this enables entirely differently.

[Rid]

Can you talk about that category of work? What do you think exists in that bucket too, earlier?

[Darren Haneen]

I think it lets us take the fidelity of the work a bit further. I've always been a designer who likes to build my work mostly out of impatience, but I like to take it as far and as close to the real thing as possible, so that when I'm deciding whether this is a good idea or not or a good solution or not, I'm kind of evaluating something that's as close to the final product as possible. But the other thing it does is it invites everybody into the process. This is like a further democratization of design skill. I think there are designers who maybe get nervous about that. I've always been one who has invited everyone into the process. I love product managers who like, show me their PowerPoint sketches, and I love engineers who show me their napkin drawings of what they think the UI should look like. Because I want everyone's input. I want to take all that and have it be an input to my process. And now they're not giving me napkins anymore. They're giving me high fidelity mockups, or they're giving me a prototype or a demo that is actually working and functional that I can play with. So it just invites everybody into the process. And by doing that, it's forces us as designers to elevate our game. And so if everybody can produce a 7 out of 10, we now need to be heading 10 out of 10 kind of as a baseline. So I think it's going to push us to further our skills as well. And I think just the expectation of what quality software looks and feels like is going to keep raising as well.

[Rid]

When you think about the week in the life of a designer at Shopify, are there specific AI native behaviors that you're hoping to see more of as a leader who's trying to turn AI into a competitive advantage for Shopify?

[Darren Haneen]

Yeah, I think, you know, there's not really a part of our jobs that I wouldn't encourage someone to try and leverage it by. At the most basic, you know, whether we're in reviews or meetings, we're using Gemini notes and we're having those notes being summarized. You can also maybe participate less in those meetings if you don't necessarily need to contribute to them, because you're going to get a thorough summary after. We've been experimenting with different models to evaluate actual visuals. And so like, hey, A and B, pros and cons, what's. What do you see? What's standing out? What are we missing? Really helpful for catching blind spots and biases and things like that. And then of course, the actual design process is trying to leverage these tools as well, where we can use them to build our ideas out a bit further. And I think, as we've all seen in the industry, design is the expectation of user experience continues to grow. And 10 years ago it might just be clicking links on pages to go from one to another. Now the best in class experiences are fluid and dynamic and evolving and responsive and reactive. And it's very hard to design those types of experiences in a static environment. And as great as something like Figma is, it still lets you draw some rectangles on a square screen. And with tools like ChatGPT and Cursor and the like, we can now take that a step further. And so I'm starting to see work from my team that is a link to a prototype that is interactive and fluid and I can play with it and I can type into it and it's going to respond to me and it might even be hooked up on the back end to a model that's doing some generative work for itself. So it's really cool just to see the type of work and the way we're communicating our ideas as a team with these tools at our, at our hands.

[Rid]

I know having an engineering founder that has an impact on the type of culture that exists at Shopify. But what is the spectrum of technical proficiency that exists within the design org right now? And do you have a new bare minimum that you expect designers to hit given all of these advancements with, with AI?

[Darren Haneen]

Yeah, I think the spectrum is large. Like, I think we definitely value the generalist. We expect people to have kind of a broad set of tools that they're bringing to Shopify. We also have a large and very talented engineering team. And so kind of up until recently, it's been efficient to leverage world class engineering talent to build out the things that we're designing. And that's allowed us to really focus on the craft and visual design and polish and interaction. But I think those lines are going to continue to blur and again, I hope it happens in both ways. I hope our engineering team is as curious about the design process and exploring design ideas with some of these tools as the design team is about understanding more deeply what it means to build software. And it's funny off the back of this like decades long should designers code question mark? Because like, you know, I was firmly in the camp of yes for quite a while just because I think it's important for a designer to understand the medium in which they're working. And having a baseline understanding of how software works and how it's built is quite valuable. But for those who didn't jump on like this is, there's no more excuses. You have these tools, you can just use English to talk to them and they will write code for you. And again, we're not quite yet at the place where we're like a designer shipping production code to our merchant base around the world. But to take an idea and then to communicate it with a proof of concept or a demo, we're there. And that's the expectation we have right now.

[Rid]

In a world where you just have a ton of prototypes flying around, how do you ensure that teams at Shopify are able to stay aligned when everything's moving at the speed of AI and it's so easy to just crank out a bunch of different experiments in every direction?

[Darren Haneen]

This is one of the reasons why I'm not yet worried about all these tools coming around as a. As a crafter and designer myself, is there is still tremendous value to be had in the vision and the taste and the strategy behind which of those ideas you pursue and how they manifest and how they are realized. Again, I think in the same way where, like, the App Store enabled distribution and all these tools and frameworks enabled building, you know, a mobile app as an example, much more easily, it didn't mean that every app was going to be successful. And there was. There were many, if not most stories where, you know, tremendous work was put in and it maybe looks great, but if it didn't create real value or solve real problem, it's as good as dead. And so I think there's still a role for designers to create a vision and to drive a team towards that kind of North Star and to ensure that, yeah, amongst these many things we're doing, they're all laddering up into a more cohesive piece. And I think that's been the challenge at Shopify is as a large organization, our goal is to craft a product that feels singular, feels like it was kind of penned by one person. To do that still requires, you know, a lot of coordination and orchestration and taste that needs to be shared across hundreds of people.

[Rid]

You have an article that I really like called Concrete Elephants. I'm wondering if you could share a little bit of that thinking with us, because it does feel very closely tied to some of the things that you're sharing now.

[Darren Haneen]

Yeah, I wrote that when I joined a new team here at Shopify a couple of years ago. Not just here, but everywhere. I've seen this circumstance arise where everybody thinks they're talking about the same thing and we're discussing a document or an idea, and either everyone agrees or disagrees, doesn't really matter. But when it comes to actually building the thing or making the thing, then you realize, oh, actually, we weren't talking about the same thing. And so what I've always pushed my teams to do, and especially designers, is to get to a concrete thing as quickly as possible, get to, like, a real visual example that is not ambivalent like that everybody can agree upon, and everyone can see and know that they're talking about the same thing. So that when we debate and discuss the merit, we're confident we're talking about the same thing. And the illustration. Illustration I use is from a parable, I think, that goes way back about some men in the dark. And they're all reaching out because they think there's an animal with them, and they're. One feels something kind of papery and thin, and one feels a rope and one feels like a tree trunk, and they're all disagreeing on what they're experiencing. And then when the lights come on, they're in the presence of an elephant, and they're all feeling and seeing different parts of it. So I've just told the team, like, be concrete and turn those lights on for the team and just put. Literally put a picture out there so that everybody can look at it and then ensure we're discussing the same thing versus anything further than that. And you start to introduce abstractions and people are making assumptions.

[Rid]

I like that because the picture doesn't even have to be correct. All it has to be is tangible, and that forces the reaction from everyone. I'm curious to learn a little bit more about the writing part of your own process. How does that work? Or what are some of the things that you're doing to kind of wrestle with the more complex ideas?

[Darren Haneen]

Yeah, this for me, really started when I worked at Mozilla on the developer tools team. All the engineers were in France and I was here in Canada. And so we were separated by six, seven hours. And so there's very little overlap, if any, most days. And so I learned quickly that I needed to become a good writer and I needed to become a good communicator so that I could work during the day and document my thinking and document the work I was hoping for them to pick up later. And kind of the quality of my writing and the quality of my communication really had an impact on the work they were able to do. Not just that it would match my intent, but also it would leave them with less ambiguity and they could better understand what we were trying to accomplish here. So I did that as kind of a practice to sit beside. All my visual design work was kind of a design document that was a living, breathing thing that was part annotation and part kind of spec of what I was trying to communicate. The other thing I learned through that process was that it actually broadened my horizons a little bit. Again, I think it's too easy to get into a tool that lets you draw rectangles and then start drawing rectangles. But when you're forced to think a little bit laterally about a problem and you're not thinking directly about the interface, first and foremost, it kind of forces you to like, really deeply understand the problem and then gives you some space to explore the solutions without jumping into, like, the tangible thing that you might end up going down the road with. And again, I'm a big proponent of getting to like, visual design work that we can start to iterate on quickly. But I've always found that kind of pre work to be really valuable in my process.

[Rid]

Yeah, it's interesting how much my own process has changed, even just since the transcription technology has gotten so good. With AI, we're like, the majority of the really meaty design work that I'm doing is just on walks and I just turn on voice mode with ChatGPT and just, just talk out loud and have it ask me questions. And words are often the tool that I use to untangle the really complex parts.

[Darren Haneen]

Yeah, it was, it was fun kind of learning that at Mozilla and then being able to reflect back on my education where you learn that different modes of communication, so writing something versus speaking something or even reading something activate different parts of your brain and different pathways. And so, you know, it's not a surprise that by speaking out loud, you're thinking about something actually a little bit differently than if you were to write it down. And it's why, you know, in programming, there's the rubber duck kind of like problem solving tool where best case you find someone to talk through your problem with. And often just talking through the problem will help you get to the solution. If you don't have a person around, just put a, you know, a duck on your desk and literally speak about the problem you're trying to solve. And in many cases, that solution will start to present itself. And I think the same is true with design problems as well.

[Rid]

The amount of times that I've started a loom video to explain a problem to someone and then figured out the solution halfway through and just deleted the loom video is just like a running joke I have with my wife now where it's like, I don't even, I don't actually even need to hit send. I just need to ask for help with words. And then oftentimes I just figure it out on my own.

[Darren Haneen]

Yeah, I mean, it's another one of the huge benefits of, of critique and things like that as a team activity, you're encouraging and, and requiring your team to talk about design and communicate their ideas orally or through written. And I think that's an often forgotten problem solving tool that's at our ready.

[Rid]

Can we talk about critique as a practice for a little bit? What are some of the things that you're trying to instill in the feedback culture at Shopify?

[Darren Haneen]

There's a few things I want to, I want to always be true. One, I think it's worth acknowledging that design can be a vulnerable craft. It's a, it's an expressive job that we play. Often the path to excellent involves a lot of kind of misses along the way and a lot of like crazy ideas or even bad ideas. And I think if you don't have a safe environment that people feel comfortable sharing those risky, provocative, crazy ideas in, they're just going to take the safe route. They're just going to take the tried and true status quo, you know, rectangles on rectangles. And, you know, the next manager up might say, ah, you know what, like, this isn't too risky, looks good to me. And you end up with this kind of like mediocre gray solution. And at the kind of like foundation of critique and feedback culture needs to be this, this safety and this environment that people feel comfortable saying, hey, this, this might be wild, this might be a terrible idea. But like, can we talk about it? Can you tell me what you think? Because sometimes those ideas are actually worth following up on or they spawn new ideas that ultimately lead to something great. And so, you know, feedback and critique always have to be productive and constructive in my opinion. They can't be a place where you go worried or scared that someone is going to speak down to you. It's always about the work, in my view, not about the person who did the work. And if you come into a room knowing, hey, everyone's here to help the work get better and help me take that work to the next level, you're going to have a really fun time. It's a really enjoyable process actually. When you can lean on world class peers, if you're lucky enough to have them to help you make their work stronger. If you go into that room and you're just worried if someone's going to think you're a good designer or not, it's going to be a very different conversation and you're probably going to bring different work. And so, yeah, safety, I think, needs to be at the foundation there.

[Rid]

Is there anything that you're able to do as a leader to practically create that safe space.

[Darren Haneen]

When I deliver feedback, I think it's important for me to acknowledge as well that I'm not always sure. And what I sometimes will quite literally say to someone is, hey, like, you've spent the last six days thinking about this problem. I've been looking at it with you for 15 minutes. So factor that into what you do with my feedback. Come back next week and tell me if I'm wrong. I kind of joke that I have, you know, kind of three cards up my sleeve per year that, you know, I'm going to lay down and say, hey, it has to be this way because of the context I have or because of my instincts here. But I want the team to engage the conversation. I want them to disagree with me. I want them to tell me, hey, actually, I've thought about this much more than you and I hear your feedback, but this is why I disagree and this is why I think we should be going in this direction. And when I know that they've thought about it that deeply and thoroughly, it gives me a lot of confidence. And like, I'm not in that room to tell everybody what to do. I'm there to ask questions, to make sure we've covered all our bases, to make sure that team A and team B and team C are thinking about problem D in the same way. And so it tends to be more of a conversation than a one way passing in feedback.

[Rid]

We've danced around a lot of different communication practices, so maybe I just want to double click and see if there's anything more there. Like when you look at the designers at Shopify and there's some subset that are really, really strong communicators, are there any other behaviors or traits that we haven't talked about that you think designers listening to this could benefit from hearing?

[Darren Haneen]

Yeah, I think the balance that I encourage to that kind of safety is kind of a culture and a mentality of winning and competition almost. And it's not competition with each other. But everybody here should, should want to produce the best work of their career, and they should want their work here and the work that their team is doing to be the best it can possibly be. I want everyone to feel like they're on like the bulls from the 90s where, like, hey, everybody is pitching in 110%. Everybody's here to play hard, everybody's here to work hard, and there is a culture of excellence. And so when you're, again, when you're giving feedback and you're getting feedback it's because we want excellent. We want 10 out of 10. We don't want mediocrity. We don't want gray. We don't want. Everyone just say, yeah, you know what? That looks good enough. You want to get feedback because you could. You want to count on your peers to push you to that next level. And so it's this balance of, like, yeah, safety. And we want a space where people can feel comfortable bringing their work, but they should know, okay, I'm coming to this environment to be pushed and to be challenged and to be. And I'm getting the feedback because my peers and my manager know I'm capable. I can do this. They know that there is more potential in the work that they're seeing, and then that's on me to. To go execute.

[Rid]

All right, so if the bar, then is bulls from the 90s, it's clear how the measuring stick there is the work. Right? But when you think about a culture of excellence, what are the bars that you then put in place for yourself as a leader to hit?

[Darren Haneen]

I think, you know, one is. Is to always try and lead by example. And so I've tried to really leverage my career as a designer when I show up as a leader, and I think it's helped me build some credibility. I mean, you can. You can ask my team if that's true or not, but I think when I'm able to give feedback, or I'll sometimes just, you know, grab something and throw into Figma and just mock it up, because it's faster for me to show an idea sometimes than to talk about it, I think when the team can see, hey, actually, he's done this before. He sat in my chair before. There is some. Some semblance that he knows what he's talking about. Like, there's just an instant, okay, cool, we're, like, jamming here. But then there's, you know, there's also the reality where, like, for the Bulls, they had a coach who probably wasn't going to jump on the floor and play, but that coach knew how to leverage that team best to win, and he knew where the strengths were and where the blind spots were and who should play, what position and what strategy to take in a given quarter. And so I think part of my role is also, like, leveraging my experience as a leader and having done this for some time to help set the team up for success. And so, yeah, like, I try and hold myself to a high bar as well, and I try not to ask of anyone what I don't think would be fair to ask of myself.

[Rid]

We've talked about prototyping, we've talked about some of the communication, presentation skills. What are some of the other strengths that you're kind of using as the coach to then evaluate what leadership looks like in practice? Are there other things that you place a lot of value on and maybe even are looking for in new candidates?

[Darren Haneen]

I think to me it all comes back to like, what are we here to do? For me, at the end of the day, it's. It's what is in our merchants hands. It's the product that is in the market is the measuring stick for me. And it's how I want our team to think about the bar we're setting for ourselves. And so everything we do in the process, all the meetings and everything in figma is valuable only if it is in service of what goes out the door and what our merchants have in their hands. And so I'm quite oriented around output and the outcome I want us all to think deeply about. Like is everything we are doing towards the goal of producing a better product and a better experience for our merchants out in the world, who in Shopify's case, their livelihood depends on it. Their business is running on our platform and we owe it to them to strive for the best. And so that kind of like bleeds into everything we do where being concrete, I want to see something that is as close to that outcome as possible early in the process so that we can be discussing the merits of that work. I want us to have the measuring stick be the live version of our product. When I was leading the retail team years ago, I would have just the app store version of the point of sale app on my phone and that would be the thing I use to give feedback to the team and I take screenshots and I'd point things out and it was just this constant drumbeat of like, hey, this is kind of the only thing that matters is what we put out the door. If we do some beautiful, incredible, innovative work and it never goes out the door, that value is never going to be realized. So it helps us prioritize and kind of like think specifically about everything we're doing towards that end.

[Rid]

I want to drill into the POS stuff, but really quickly just to go a bit deeper on some of the things that you were just saying. There is like this gap, right, where you can make a prototype that feels very, very real, that doesn't exist in production. Right. And if the only thing that matters and the measuring stick is what the merchants are using on a daily basis, there's still a chasm that you have to close. And you know, that's a lot of ambiguous impact strategy work as a designer. So what else goes into that gap that designers should be thinking about when they're trying to get to the point where, yeah, their ideas, there's buy in, you know, like, we're actually going to commit to doing this and putting resources behind it.

[Darren Haneen]

It's one of my favorite topics here as well, and I think marries to some of the AI stuff that we were discussing too, where like, once you've been doing design work for, for any amount of time and you kind of feel comfortable in the tools, getting to that, that kind of finished prototype or mock up, it's not easy, but it's the thing we're very good at as people who do this professionally or people who do this as like, as a thing we really enjoy doing. What I found to be extremely difficult, even at world class companies like Shopify, is that space between, okay, this is what we want to build and then this is what we built. And Jared Spool's definition of design here, the rendering of intent has always stuck with me because, like, maintaining the integrity of your intent through that process is tough because that's when you're actually going to face the constraints of reality. You're going to face challenges with timeline and how many people are available and the skill set of the engineers you're working with. Maybe, maybe this is a thing that needs to coexist with other parts of your product and you realize, hey, actually there's some overlap here. We need to, we need to untangle. I've always maintained that design is about compromise, like good design is about compromise. And it does not mean compromising down from excellent. But it's the reality that, hey, you're going to have to make some decisions along the way. And the way you make those decisions ultimately will determine whether the output is excellent or whether you got a C. And you can have the same starting point, take two very different paths through the build and end up in two very different places. And so again, I coach my team, I coach my designers. Like, you have to stay close, you have to stay engaged with the engineering team. You have to be testing things on a daily basis. I want to see builds on our phones and builds on our laptops regularly that we can evaluate to make sure, hey, we're not losing integrity here. We're not watering down our solution because of xyz, because there's always going to be Questions. There are always going to be constraints that come up along the way, and how you handle those is really important. And again, when we get to the retail stuff, there's some hardware. Hardware is a different beast, but I think it kind of magnified some of those challenges.

[Rid]

Let's talk about that then. So you got to do retail pos massive project. What's the backstory there? Can you give us a little insight into what that's like as a designer?

[Darren Haneen]

We had a team in Ottawa who was working on our point of sale app. It was actually built as a proof of concept out of a hack days, which we do on a quarterly basis. They were building out a bunch of stuff and they needed some design support. And so someone just asked if I could do them a favor and work on it kind of on the side of my desk, which I was happy to do. And it was around the time when we were ramping up our investment there and starting to take point of sale a bit more seriously in this retail segment. More seriously. Recognizing that a lot of merchants want to sell online and offline, and having a solution that kind of spanned both channels was really valuable. And so I started building up the team from 1 to 2 to 6 to, you know, whatever it became in 2022. And I finally moved on from that team. And along the way, the question was asking me as well, hey, do you know anything about hardware and industrial design? Because we're going to be doing our own hardware too. And I said, I don't actually, but, you know, I. I think I can figure this out and, you know, if I just treat it like the other design work I've been doing, what could possibly go wrong?

[Rid]

That same recent grad mentality.

[Darren Haneen]

Yeah, it was. It was kind of young, me being a little confident. But again, back to my. My freelance days, like, that was the. That was the M.O. it was like, hey, take whatever job you can get and figure out how to do it well. And so I just hired industrial designers, a couple from BlackBerry and some folks that really knew what they were doing. And then my job was to help them produce great work inside of Shopify. And so, yeah, for about six years, led both the software and hardware sides of the retail business here.

[Rid]

I mean, for someone like myself who has absolutely no background in hardware, I don't really understand even what that entails or how much it even differs from a traditional design process that maybe a lot of people listening are more familiar with. What are some of those big differences or things that you were wrestling with that were unique to hardware.

[Darren Haneen]

Maybe two main differences I found. One, I think all design work has a cost associated with it. We just don't often think about it as much on the software side because that cost is like, sometimes it's bandwidth, sometimes it's just people hours to build the thing, sometimes it's compute time. Like there's different costs. But it's rarely part of our calculus when we're doing design. Whereas with hardware, you know, early on we're talking about CMF and colors, materials and finishes, and this plastic versus that plastic have a different cost per gram. And if we want to use a little bit of aluminum here, we need to make sure that that's budgeted into our actual costs of this hardware and that we can produce this hardware so that we can sell it at least as a break even. And so there's all these considerations that are deeply impacting the design process. Because yeah, of course we'd love to use, you know, aluminum and glass and all these fancy materials in everything we do. But there's a, there's a trade off that has to be made as part of the design process. The parallel there is every design decision is a product decision and every product decision is a design decision. And so it's not so different than the software side of things. But it becomes a lot more apparent early on in the process. And the other big difference was just how much more of a one way street the hardware development process is. There are certain gates and checkpoints you hit along the way where it's very difficult and again expensive to go back. And so with software, it's all ephemeral. You can ship it today and you can change it all tomorrow and you can iterate and you can try things and you can ship 10 things and figure out which one performs best. Whereas with hardware we had to think, hey, we're going to be shipping this thing two, three years from now. Every decision we make along the way needs to be a little more rigorous, a little bit more methodical, a little bit more thoughtful. And it was fun because we got to go back to this kind of like slightly more old school way of doing design where we had, you know, rough prototypes made out of clay and foam and we were doing a lot of usability testing and we were getting people to just hold it in their hand and see how it felt. And we were, we were putting a lot more rigor into each design decision along the way. So that when we committed to manufacturing a mold for the plastic overseas, we knew we weren't going to change our minds later because we had put in, we put in the work. And yeah, as someone who studied the sciences through my schooling, this rigorous methodical process was like, it felt very natural to me. So it's quite fun to see that play out.

[Rid]

So you've been at Shopify for over nine years now. I would imagine there's quite a few stories and experiences and I'm wondering if there's anything else that we haven't talked about where when you look back, you're like, you know what, that was a pretty significant tipping point in my journey in this company or lessons learned, or even just a story that you're proud of where you're able to make an impact that people listening could draw something from.

[Darren Haneen]

I think one for sure that has stood out for me and it's on my, my desk. Behind me here was when we won a Red Dot award for one of the first hardware products that we had shipped. And at that time I was not messaging Toby very often. He's from Germany and the Red Dot organization has a lot of kind of German background. And I knew he actually read the yearbook as, as a, as a young kid. And that was a lot of his inspiration behind designing excellent products. And he's always wanted Shopify to be an excellent product. And it was very fulfilling to be able to send him a message when we won and let him know, hey, FYI, Shopify has got its first Red Dot award. And so you can put that on your wall as well. And we had a copy framed and sent to him. And this was, this was years after that initial conversation about doing hardware at Shopify. And so I like the long game. I like things that just take a little bit of work every day over a long period of time. And this was a really satisfying conclusion to a kind of a three, four year story where a lot of that time was just spent in the basement of one of our offices because that's where they, they put the hardware team so it wouldn't make a mess. And, you know, putting pictures on the wall and making a lot of guesses and a lot of assumptions and a lot of decisions that didn't see the light of day for a couple of years. And so to see some validation and especially from such a recognized body was just a nice feeling to be able to bring back to the team and say, hey, look, like we did this thing, we did this really hard thing. We're a handful of people, it was less than 5, and we have competitors probably with teams in the hundreds. And yeah, we did this thing. And that was a cool moment, for sure.

[Rid]

Less than five people on the team, that was not in my brain. I was definitely expecting a whole other zero on top of that.

[Darren Haneen]

On the hardware side? Yeah. Less than five.

[Rid]

Wow. So you're wearing all kinds of hats.

[Darren Haneen]

Outside of my day job, I love products and things that are made by a single person, like video games that are made by one person are dear to me, and movies that are kind of authored by a small group of people. I think there's just something special to that authorship that takes place. And we were able to experience that here, I think, in a pretty unique way, where typically you would have tens or hundreds of people working on products of this magnitude. And I think each person on the team was able to feel a very direct impact on the shape and form of everything we were producing in that little lab.

[Rid]

Does that experience influence the way that you think about staffing or organizing talent on the software side?

[Darren Haneen]

It does. I think I'm always hesitant to have too many people thinking about the same thing at once. I think often the best work that's come out of teams I've been responsible for has come from a person thinking about something deeply and, like, kind of having that latitude inside their head to kind of go into a whole bunch of different places and think about something. There's that article, the cost of craft, and there's like, this understanding around the bigger team is there's communication overhead. There's just even one other person. Suddenly you have to communicate your thinking and your rationale, and there's a benefit there. As we discussed earlier, there's a lot of opportunity to deepen your understanding of something, but it can slow you down and it can add friction. And so I also am interested and curious to see, hey, when one person just, like, takes a problem and just, like, goes really deep on it, where do they end up? And some of the most interesting kind of innovations I've. I've been part of with the team. Sometimes it's just a Monday, and someone comes in like, hey, I had this idea, like, I've been thinking about this all week, and it just kind of hit me last night, like, can we try this? And those are often the things that tend to be as successful, if not more than when you say, hey, you five go and, like, figure that together. Because then you're suddenly designing for consensus, which often doesn't lead to, like, the spikes and, like, the global maxima that you're looking.

[Rid]

I'll link the article that you referenced, Cost of craft in the show notes. It's George Kenneberg. One of my favorite articles. I think I've read it at least three or four times. And it documents really just what happens as a company scales and, and all of the different ways that Kraft can kind of seep through the cracks. You talked about creating space for almost bottoms up ideation. Is there anything else that you're doing at Shopify level scale to ensure that this bar for craft is consistently hit?

[Darren Haneen]

We have a combination of bottoms up thinking enablement. So we have our, we have our own internal kind of project management software that we build in inside Shopify that's like perfectly tailored to our needs. And every project starts as a proposal. And a proposal by design is this very lightweight kind of a one pager. And the beauty is that anybody can submit a proposal and so it can be a designer on the team, it could be an engineer, it could be a product manager, someone in marketing, someone in legal, whomever. And that proposal goes into the process and the first step of that process is kind of alignment with that group's leadership team that this is something worth investing in. It's this nice marriage of like bottoms up thinking and you get everybody who's like in the weeds thinking about these problems every day able to propose things they think we should be doing or doing more of. And then there's this kind of filter of like, okay, someone like me who's responsible for a portfolio of work, I want to make sure that this is fitting into our strategy and the trade offs that we would be making to invest here are worth it. I can kind of apply my strategic lens to things, but it's not a company where like, you know, a couple people go into a room and draft a six month roadmap and then deliver it to the team. And this is what we're doing.

[Rid]

I mean it's easy to have a very generic answer to a question like that, but you literally built internal software to facilitate the bottoms up. Like that is putting your money where your mouth is. My question then is, are there common characteristics of the proposals that you are giving your stamp of approval on?

[Darren Haneen]

Like, I think there's the things that are kind of like strategically interesting, like hey, this might, you know, bring more merchants on the platform or allow those merchants to onboard more success. I'm being very generic here, but like there are things that start to make sense within our kind of strategic framework. And on the growth team we have goals and we're trying to better those goals. And so there's things that I can See a direct line to. But the things I'm. I'm maybe most interested in in my role are the things that just make Shopify a better product and a better experience for our merchants. Because I fundamentally believe a better product will allow people to understand it better and will allow them to onboard to it more easily, and they'll ultimately have more success with their business if our product is continually like pushing the bar of what it is. And one of the things I tried to bring to the Grow team when I joined a couple years ago was that just making Shopify better is enough. Like, that is where we can stop the discussion about whether we should do something or not. If you show me a proposal that is making a part of our product meaningfully better, I'm interested and we'll talk about that. And those ones maybe don't even need metrics to go along with them. Because I think organizationally we share a conviction that, hey, the better our product is and the easier it is to use and the more delightful it is to use, the work will speak for itself.

[Toby]

I'm a big believer in the power of video to explain my thinking as a designer. So when it's time to get feedback, I'll drop a loom link and slack and another link to a Figma prototype.

[Rid]

And feedback will be scattered everywhere.

[Toby]

And I mean, it's a mess. So I'm building the product that I've always wanted to exist. And it's called Inflight.

[Rid]

You can kind of think of it.

[Toby]

Like an async crit. It's an easy way to share a video walkthrough along with an interactive prototype or whatever you're designing. And then AI interviews the people on your team to get you the feedback that you need and organizes everything for you in a beautiful insights page. So right now I'm only giving access to dive club listeners.

[Rid]

So if you want to be one.

[Toby]

Of the first to use Inflight, head to dive, dot, club, slash inflight to claim your spot.

[Rid]

There's this tension that's coming up a lot between the numbers and taste. And I think it's very easy to say, well, yeah, taste is so important. But then you're in a growth design org and it's like, well, numbers run the world there. So for you to have that perspective and so still emphasize the importance of taste is very interesting. I'm underlining that for myself.

[Darren Haneen]

Yeah, I think, you know, Shopify is a company where the craft is king and the quality of our product and the quality of Shopify is. Is kind of the ultimate measure that we all hold ourselves accountable to. I think Toby said in the past, like he's very aware that Shopify was successful early on in part because of its, you know, technology, but in a large part because of the design and the interface. And you know, if you break it down, engineers build really powerful technology. And again, kind of like the work that never ships. If that technology is inaccessible to the general population or your user base, it's valueless. And design plays this really fun role in the middle where we literally create an interface that's more interface designers. We create an interface between that value and the power of that technology and the people who need to use it. And so making that interface a better, stronger, more intuitive, more enjoyable one is value in itself.

[Rid]

As someone who very clearly is able to see the opportunity cost in different decisions, how do you think about the trade offs that you're willing to make in order to continually hit that bar?

[Darren Haneen]

Yeah, like everything, it's got to be a portfolio approach. It's how we think about infrastructure versus experiments in the grow team. But it's also how I think about there's a certain percentage of our work in a given quarter that I'm comfortable saying, hey, this is just quality state of the business, like product improvement, Glow up style work that's just making Shopify continually better. And then there's a part of the portfolio that is like we need to do these things to continue to grow our business, maybe in new locales or new regions or towards a new segment. And then there's a small part at the end which is like kind of the bets and the experiments where we're like, hey, we also need to just be trying some stuff that might totally flop but might also be a meaningful lever we can pull in the future.

[Rid]

You're making me laugh with Glow Up. I, I again, another one of those phrases where like with someone with a very like, you know, quant growth background, I wouldn't have expected you to say.

[Darren Haneen]

We had a project last year, I think just called the Sign Up Glow Up. And that was, that was how it was known internally and was what it sounded like.

[Rid]

You know, a topic that has come up recently on this show that is related to that is just at these bigger companies, like where is the threshold of craft that you are expecting designers to be able to hit? And I'm going to talk about it through the lens of someone listening that I'd like you to just kind of speak to. And it might sound a little bit complainy, but I know at Least some subset of the industry right now is feeling this pull in all directions where, you know, listening to Darren talk and, you know, I gotta be able to like do glow ups and build code prototypes and pitch my ideas. And it just feels like every single week we wake up and the tent poles have been moved out. For what it means to be a designer. I'm curious if you have a way that you're thinking about that or something that you'd like to say to that person who's listening.

[Darren Haneen]

Yeah, again, I think having seen moments like this before, I just constantly center myself around the role of design and the role of the designer being about solving problems for people. I think in most cases, if that remains true, you know, there's always work for us to do. How we do that has changed and is continually changing and is changing maybe this year more than ever. You know, I think gone are the days of sticky notes on windows and gray wireframes and marker drawings. Because everything today especially needs to be in service of the outcome and like the visual design and the, the craftedness of the final product. And so if you find yourself struggling to produce that kind of like that type of outcome, work backwards. And I often recommend to new grads or people who want to get into the industry, like, do what you would do if you were learning how to draw, like just copy a bunch of stuff, like don't say it was yours. But like, the way you can learn is by taking something that inspires you or that you find interesting and just see if you can replicate that. And, you know, maybe do it in Figma first. But hey, maybe take it into ChatGPT and see if you can build that as well. Because you're going to learn a lot by studying and looking closely at how something is put together and why different decisions are made. And you may notice, oh, hey, both these margins are 8 pixels. Like that must have been on purpose. And, oh, maybe that's how you think about these things. And by looking closely at something, you're going to teach yourself and you're going to learn a lot about how world class work is done and then you kind of can work back from there too. And so it's like, okay, well, why did this thing that I admire, why does this exist in the first place? Like, what problem are they trying to solve? What do I know about this company? And like, what might have been their strategy here and what might have been the thinking? And a lot of this just sounds like homework, but I mean, you just got to put in the reps you got to do the work, you got to practice, you got to just like, do design over and over and over, and you got to produce a lot of work. You know, Hourglass had that great video on taste and the gap. And, you know, to simplify it, you know, you often know what great looks like or you can, you can kind of identify it. But getting there is really hard. And the only way to get there is just to do the work. Just to do the work and put in the reps.

[Rid]

I mean, it sounds like homework, but at the same time, it's like, this is why we design too. You know, Like, I can't pick up a product without continually asking why and trying to figure out, like, reverse engineer the strategy or why something works a certain way. And so I also hope that for a lot of people, that kind of thing happens naturally just because you love the practice. Right?

[Darren Haneen]

Yeah. I think there's, like, a curiosity that really sets some designers apart when they look at, you know, I can't go anywhere without looking at, like, the, the design of the thing or the, the UI on the movie ticket thing. It's just the way my brain has learned to function. But I see it in a lot of people I work with, and I see it in some of the most promising designers I meet in the interview process is like, they're just curious. They just want to understand, like, why stuff works. They want to understand why things are successful. Like, why do they, how do they work functionally? But also, like, why did this product succeed and this one failed? I think is a really interesting question to ask yourself if you're studying design. And, yeah, like, it's a creative pursuit, it's a creative job, but treat it like something like a lifelong pursuit. It's something to study and to master. And there are plenty of excellent books on the foundations of design that are as relevant today as ever. And so, yeah, it's a lot, but I mean, there's no shortcut. You just got to start with something and, and work your way towards it and recognize, like, okay, these are all tools I need in my toolbox. I'm not going to pick them all up at once. So, like, what one or two or three do I want to start with? And, you know, I can pick the other ones up later as I, as I grow.

[Rid]

You mentioned curiosity. Are there other traits that you notice in the more promising younger designers?

[Darren Haneen]

I think, again, there is so much product design out there. It's so easy just to emulate and to be maybe too inspired by the greats And I'm always really excited when I come across a portfolio or someone's website that like, surprises me. Even if the execution is like, you know, if I have notes or something, that's fine. They're thinking about stuff in a way that is different than what I've seen before. And what that tells me is that they're thinking outside the box. They're not just like going to whatever replaced dribble. Like, they're not going on the Internet and like picking the top 10 things and trying to just like fit into that mold. They're, they've thought deeply about what they want to put out into the world. And, you know, I think that that type of thinking is really valuable. And then just generally like, people who are willing to like, engage in hard problems and work through solutions. Again, this is a job that many of us do professionally and it's going to feel hard at times. Like, I tell my team this all the time because that Shopify, the Grow team, works with almost every other part of the business. And there's a lot of orchestration and there's a lot of collaboration and it's a really fun, healthy process generally. But I tell them, like, hey, to ship this thing, like, you're gonna have to go work with these six other groups and you'll have to get alignment here, here and here. And like, this is gonna be hard. Like, this is gonna feel hard, but, like, what else are we gonna do? Like, this is the thing we need to do. This is the important work, this is the valuable work. There's no shortcuts here, so let's just figure out how to get it done. And people who have that, that mindset I've seen be really successful here.

[Rid]

Going back to something that you said a little bit ago, you talked about this risk taking behavior. And I'm wondering if there's an example that you can point to from your time at Shopify that you think emulates what you're kind of looking for in other designers.

[Darren Haneen]

Yeah, I mean, going back a couple years, we had a very different structure around our trial. For Shopify. You used to get, I think three days free, and then you were jumped into a full, a full paid plan. And then I think at one point we had 14 days trial and then straight into the full, full paid plan. We had this hypothesis that like, hey, it probably takes more than three days or even 14 days to start a business, like to be in a position where you actually wanting to start to pay for a product that's helping you run your business. And going even further back, we had tried a longer free trial where we said, hey, you can have like, I don't know, it was like three months or something for free before you have to start paying us. And it actually didn't work out very well. And we found that the shorter trial was. Just worked better for us and for merchants. And then fast forward a couple years and someone brought back to the table a new trial structure which was, hey, let's give you a day or two for free, but then let's give you an extended period for a dollar per month. Like, let's get just a little skin in the game. Let's. Let's have you take your credit card out of your wallet. We're literally asking for the least amount of money we can reasonably ask to put on a credit card, being $1. And then let's give you lots of time to, like, try our product. And let's. Let's be confident that our product will sell itself at that point and that they'll be able to onboard and either bring over their existing business or get started to the point where at the end of those three months, they're ready to pick a plan if they've seen enough traction. And if you look on Shopify now, that's the structure we have. And so it's safe to say that worked extremely well. And just this. This tiny little tweak of, hey, let's get some skin in the game. Let's try again. It would have been easy for many people to say, and we tried that. We actually tried free, and it didn't work. So why would a dollar work? But we were comfortable. We took the risk. We rolled it out to a small group just to see. And it's that kind of thinking and that kind of appetite for risk around even just something as fundamental as our pricing model that makes Shopify like a really interesting and fun place to work, for sure.

[Rid]

It also speaks to the culture of celebrating and encouraging ideas, too. Like, that's just like a theme that I'm kind of tying through. A lot of the things that you're saying where from the outside, it looks like a lot of the designers who are having a lot of success and making a big impact are the ones who are just. Just coming to the table with ideas and making it happen.

[Darren Haneen]

Like, it's a shared responsibility across the company. Everybody is expected to act like an owner, and everybody can contribute to our strategy, Everybody can contribute to our roadmap, Everybody can propose things they think we should be doing and it's, it's not the exception that we take those proposals from here and there and, and bring them into our roadmap. It's more the norm. I think as a crafter, really exciting environment to be in where when you have an idea or you want to discuss something, you want to start to get feedback or something, we have a forum for that and we're actually encouraging that rather than saying actually no, we have all this work lined up. And so like, you know, not right now.

[Rid]

I think that is the big difference in my mind where you have an existing structure and pathway for those ideas to be funneled. Where historically the different orgs that I've worked in, it's felt like I had to really go 0 to 1 on this idea and almost like introduce it into the rest of the process and everything that's happening. Like it's a little bit intimidating, right, to like write a doc and drop it in slack and say, hey, I know we're not thinking about this and we have a chock full roadmap, but we should do this. You know, that's not always easy to do as a designer.

[Darren Haneen]

Yeah. And we do demo days and we've got lots of opportunity for people just to like share the work they're doing. Like I said, we do hack days very regularly and it's often like two or three days. So it's more of a hack week. But the mandate is like, put everything you're normally working on down and take that thing that's been bugging you in the back of your head for the last few weeks or months and like find a couple people and build it. And the number of things that end up going on to ship or become actual features or products as part of Shopify's portfolio that were born in hack days is staggering. Like, it's, it's a really fertile breeding ground for those nascent ideas to come forward. And I, I love that. You know, right from Toby down, this is something that has always been a part of the culture here and is something that we continue to do to this and it just really fosters and encourages everybody, like, hey, no bad ideas. Like just try that thing. And then we've got a cool, you know, another cool tool for like, you get to view all the different demos that are produced and you can vote on them. And yeah, it really celebrates like that innovative, out of the box thinking.

[Rid]

I remember being at Shopify Unite like 7 years ago and it was this really weird weekend where the power went out in SF for like 36 hours or something crazy. People thought it was a terrorist attack. And you all did great. You all brought a bunch of mimosas. And we're sitting on the pier and I'm talking to this Shopify designer who was explaining to me about this hack week project and I think it became called Frenzy maybe. Yeah. And it was just like listening to that person talk about this idea that was a two day hack and then got real resources put behind it and now it's this, this app in the App Store with Shopify, you know, stamp. And I was just blown away that something like that could get so much momentum inside of a company like Shopify.

[Darren Haneen]

Yeah, Frenzy was a cool solution to like all the drop sales and flash sales that were happening for a period of time. And kind of like the traditional online store was just getting overwhelmed by sudden traffic. And so we built this really cool product that enabled some of our celebrities and kind of larger merchants to run these flash sales. But you know, the Shop app that I'm sure many people are familiar with actually started in Toronto as well on my team as Arrive. It was originally known as Arrive and it was a package tracking app. And it wasn't part of hack days, but it was part of a kind of a garage initiative we were trying at the time where we were just committing like some portion of our time to try new things. And we thought, hey, like, why does the journey need to end once you've purchased something from Orange? Why don't we actually help you track that package all the way to your door and then maybe give you an opportunity to like repurchase or re. Engage with that, that merchant or for the merchant to engage with the customer. And a point of sale, like I said, was another hack days experiment. Just, I think someone just said, hey, I wonder if we could build a point of sale app off of our checkout APIs. And they got, I think, you know, 80% of the way and realized, hey, we only need to add a few more things. And then we've got, you know, a fairly robust point of sale product that we can start to build out. And so, you know, a lot of the, a lot of the big wins here have come from that, you know, not something that was put on a roadmap in a boardroom, but just something that a few people just started to work on and try and found traction that way.

[Rid]

I can't let you go before I take a hard left and ask you about the last few years where you've been dabbling quite a bit in board game design. So I'm curious, like, what has that been experience, like, and is there any part of that that then funnels back into how you show up at Shopify?

[Darren Haneen]

Yeah, I've always been more on the video game side of things. Like, I enjoy playing playing games. And then going back to 2013, I think I had this naive thought I'd learned enough programming at the time, and I'm like, I bet I could make a video game. And just bit off a little more than I could chew. But started working on my first video game that ended up releasing in 2015 called Lastronaut and then in Covid when in Canada. Here we were under lockdown for a fair bit of time. A friend of mine just messaged me out of the blue and said, hey, I have this idea, like, can I call you tonight? And he had thought about this concept for a board game, but he needed someone to help realize it and do some of the art and the creative. I had nothing else to do at the time. I was at my house 247 and really was excited about a creative outlet like that. And so I spent close to two years with him, like designing and then manufacturing. And we did a Kickstarter and sold this board game that you can still find. And then since then, I've also been picked up a few more video game projects. And I just, I find games, especially video games, it's like really interesting confluence of like art, music, design, writing, technical, like programming opportunity. And so it's a fun. A fun way for like me to have a project where if I feel like writing some code that night, I can. If I feel like writing some music that night, I can. If I feel like drawing that night, I can. And it's all towards the same project. And so it gives me something that again, a little bit of work over a long period of time. And in all these different forms of media that, yeah, I just find them a really fun way to. To keep myself busy outside of work.

[Rid]

Amazing. Well, I'll drop some links in the show notes for anyone that's interested. And Darren, this has been great. Thanks for coming on and sharing a little bit about the culture and how you all work and your background. Super insightful and I really appreciate your time.

[Darren Haneen]

Yeah, thanks for having me and for. For keeping this podcast going because I've. I've loved and have learned a ton of from the episodes and hope to hear many more going forward.

[Toby]

Before I let you go, I want to take just one minute to run you through my favorite products because I'm constantly asked what's in my stack. Framer is how I build websites. Genway is how I do research. Granola is how I take notes during crit Jitter is how I animate my designs. Lovable is how I build my ideas in code. Mobbing is how I find design inspiration. Paper is how I design like a creative and Raycast is my shortcut every.

[Rid]

Step of the way.

[Toby]

Now I've hand selected these companies so that I can do these episodes full time. So by far the number one way to support the show is to check them out. You can find the full list at Dive Club Slash Partners.