Katarina Batina - Making big bets with design

[00:00] Initial discussions around some of the prototypes that we had created were making a lot of product managers and data scientists a little nervous saying like, wow, this really thwarts what we understand best practices to look like. People come to do great craft work, but they leave really great product thinkers. And that to me is one of the most enduring skills in this era. [00:30] from like jumping the pond here and like embedding myself in that craft or in that skill set or learning it so that I can come to my own conclusions about this thing.

Welcome to Dive Club. My name is Rid and this is where designers never stop learning. Today's episode is all about what it takes to make big bets with design because we get to talk to Katarina Bettina who's the design director behind [01:00] day. They did things pretty differently and it worked. So we're going to get into the weeds about how they explore new ideas, how designers are making the most out of AI, what it takes to consistently hit this bar for craft, and a lot more. So let's dive right in.

Shop I talk about is a [01:19] love child of two really cool internal projects at Shopify. One was called Arrive for the OGs in the crowd. Like they'll know that that was kind of the [01:27] origin story of the app. And it was to solve a merchant problem, actually. Getting a ton of support tickets into their local queues saying, "Hey, where's my package?" And us, as Shopify, being extremely merchant-centric, wanting to say, "Hey, that's a problem we can solve." The other connection point for Shop was something called Shopify Pay at the time, which was this

[01:48] sneaky little checkbox that just said, hey, next time you come through a Shopify-backed online store with the Shopify checkout, [01:55] Your stuff will be her. Six or seven years ago now, brought those two products together underneath the banner of Shop. What an audacious brand name, by the way. Who has the guts to do that besides Shopify? I love it so, so much. It creates some funny branding problems sometimes because it's like the verb, the noun, the app, the everything. Bringing those things together, there was this third pillar of like, we've got this brand.

[02:17] payments network thing. We're becoming a trusted source for people as their kind of chopping identity. And then we have package tracking, which is such a beloved feature even today. But we knew that there was this huge opportunity, obviously, to become a first party platform that merchants could really trust. Toby has always had an incredibly strong vision for what a merchant first, [02:38] merchant led shopping destination can look like that buyers can fall in love with. I really credit where we are now in our vision to [02:46] that really audacious prompt.

[02:48] You know, most people who work in commerce or really any modern consumer app are so used to being like they found their one flywheel and they are just milking it. [02:57] super data-driven, extremely micro-optimization focused, [03:03] And what's been crazy about our journey in Shabba is we've been able to paint with very broad strokes, [03:07] against very bold ideas. [03:09] And one of those bold ideas has been taking a completely different tact with the browsing experience. [03:14] saying, [03:15] Things like, we want this to be a place that you come when you're bored and you want to shop.

You think about shopping kind of in a more romantic way in the offline world. Shopping is a form of entertainment. It's a way to engage with culture. And so many of the brands that launch on Shopify represent the best of what that world looks like, right? And when I think about the interface and when we think about the experience in shop, we think about on purpose how to do things a little differently. How do we celebrate those brand stories? How do we bring them to life? [03:45] and engaging. And through several iterations, we've arrived at [03:49] what we call today our super feed.

There was like feed version one. The super feed became something that was extremely content driven and focused and highly personalized. And we're working on our next iteration right now. Real quick message, and then we can jump back into it. Okay, so get this. Jitter's latest release lets you build your own creative tools inside of Jitter to make custom animations and effects. Just describe anything you want, and then Jitter will give you custom [04:19] 3D control, dithering, or even an old VHS filter. And then once you get the effect where you want it, you can save it, share it with your team, and easily reuse it across projects.

And it really is as simple as just typing out your ideas, which is perfect for someone like me that doesn't have this rich background in animation. And sometimes I even like to have Claude help me with the prompts. This feature has blown the roof off of my creativity, and I cannot wait to see what you [04:49] club slash jitter to get started. When you're prototyping with AI, if you're spending time recreating styles, components, and layouts from your actual product, I got news for you. You're probably wasting time and definitely not using the right tool either.

That's why I love recommending Dessin to teams. In one click, you and everyone on your team can prototype directly in your code base without ever opening an IDE. Dessin extracts your design language and gives you the perfect [05:19] to explore without any of the technical hurdles. It's a pretty big deal and you can connect your code base and start prototyping today. Just head to club slash dessen. That's D-E-S-S-N. Now onto the episode. I want to talk a little bit about those iterations because you talked about shopping as entertainment and I feel that.

I know that I've said this to you off record. I'm going to say it again just so that it is on record. The shop app is the only app that I will browse without [05:46] clear intent, which is a little bit dangerous. It's like the I can't fall asleep app for me. I know. I feel like I've blamed a lot for people shopping more recently. I know. Yeah. My wife doesn't love it. We'll put it that way. But I want to know, what are some of those iterations that you've made?

How did you get this to the point where [06:04] I am just kind of laying in bed scrolling through this app. Absolutely. Well, one of the biggest tension points was around the thought of density, right? So if we think about what makes modern consumption interfaces really successful, its density of information, collecting intent, you know, are people liking products? How many products can you get into one view scroll? You know, all of these best practices that have led to a lot of the commerce interfaces we're all pretty used to, but we really wanted to make a...

[06:32] quite a different decision to say, how do we make this feel more like window shopping? So each viewport provides an opportunity to kind of portal into a particular brand story, a particular product recommendation, whatever it may be. [06:45] Trust me, initial discussions around some of the prototypes that we had created were making a lot of product managers and data centers a little nervous, saying like, wow, this really thwarts. [06:54] what we understand breast practices to look like. And I feel [06:59] Truly lucky to work in an organization that's just willing to build a thing and take the bet.

And certainly in our first couple of iterations of this, it was not at all a slam dunk. Our recommendations algorithm really needed to be on point and able to serve that kind of consumption model. I think one of the other huge unlocks has been how we've been able to very thoughtfully and gently deploy AI to bring more of this content to life. Our first couple of iterations in what we call today the super feed were very static. [07:29] cards. [07:30] ultimately they can feel a little flat at times. And one of the things we've been working on in shipping more recently is bringing a little bit of video generation to just create a little bit of life and interest in the feed.

And that's gone a really long way. [07:43] The other thing that we've recently introduced is merchant posts. So merchants actually be able to syndicate content from the other services like Instagram and TikTok, where they're already producing and showing content, bringing that into a commerce native environment where they can tag the products. Those products can be purchased right there. And it's really, really bringing our feed to life, which is awesome. [08:02] You talked about big bets. One of them, for sure, like the window shopping, single merchant at a time, that feels obvious as one.

Are there other ones that come to mind that we could maybe talk about and use as a window into your process and how you even evaluate these ideas? Another huge bet that we've slowly been teasing out, and it's kind of downstream from the feed, is really the manifestation of what we call the shop store. So today, the swan song of any merchant's experience using Shopify is getting to build their online store. [08:32] on the internet to really tell their story. The great thing about the online store is that it is endlessly configurable.

You can go headless off of our main frame and build whatever you want. The themes are endlessly extensible. That's the whole point. It's to maximize merchant creativity. The tension that we've had coming into shop is wanting to have a uniform enough experience that there's cohesive browsing for buyers, but also not to limit merchant expression and storytelling. [09:02] something that Luke Dupont has been working on [09:04] He helped to kind of generate the first version of the shop store, or I should really say the second version, where suddenly the stores, many might have noticed like last kind of holiday shopping season.

The store suddenly felt a lot richer. The storytelling was there. There was a lot of video. You know, we allowed brand word marks to bust out of the like trapped in little avatar and like let them sit as real SVGs that feel rich and feel owned. [09:34] for us from a data perspective is actually getting all of the online store content to feel native within the shop store. And the prototyping that Luke has been spearheading here has been honestly incredible. There's been longstanding data structures and the way we conceived about data within the online store that initially made it hard to imagine just translating that easily to shop.

What's been so cool about this project and this bet in particular is watching Luke and other [10:04] And it's been because of AI wholeheartedly, right? His ability to develop the set of prototypes that are able to express this idea, but actually get into the real data and not just, you know, hand wave his way through this has been truly remarkable. Can we go another level deeper there? Like, what are those prototypes consisting of? How are you even giving designers access to this data, to the code base? Like, what does that prototype look like in practice?

Because I know a lot of people are nodding along as they're listening. [10:34] there's a lot of little hoops and hurdles to get through along the way. The favorite setup right now is designers working with a harness like Pi, using something like Cloud Code, plugging directly into production data sets, being able to pull those down and develop whatever kind of experiences they want. And so in the example of Luke's prototype, a bunch of work has been done, thankfully, in our developer experience team to develop, [10:59] make it safe for us to be playing with this data without all the kinds of unfortunate accidents that could come.

And so his process has really been talking a lot to Claude about [11:10] really philosophically, the concept of what he hopes to build, developing a plan and then going back in and actually developing. His prototype is really fascinating because it's not just one end-to-end feature. I think [11:22] A lot of times when we're talking about prototyping, it's I've got, if we're talking about shop, I've got the simulator up and I'm going to build a new feature end to end, which we're doing too, and is awesome. What he's really doing is creating a whole world to conceptualize of a new product direction.

So when you get in there, you'll see like a whole grid of different merchant storefronts. You're able to click in, configure the different data blocks that are actually being fed by the [11:52] internally in something we call quick, which allows us to get something up very quickly and send each other links. So we get out of that problem where everything's living locally. Everything's hosted and can be shared internally super easily, which I'm very grateful for. I want to get into the AI piece, but first I want to return to a thing that we've kind of been touching on from different angles, which is this relationship between...

[12:14] like metrics and [12:16] the quality bar and the core vision of what you want to create with the shop app? Because I'm sure sometimes these big bets just works. The graph go up, great, everybody claps. But it's probably not that easy, I would imagine. And so can you talk a little bit about... [12:31] how you wrestle with that tension. Because Luke has this amazing vision, this amazing prototype, everybody gets super excited, but then the results aren't exactly what you want. It's a really important part of my job, I think.

And part of it's setting the grounds, having an intimate understanding of what our business goals are and having an intimate understanding of what our performance looks like for us. So it's not to say that I or any of my colleagues live in La La Land. It's actually having an intimate awareness of these things that allow us to move forward. And one of the keys is [12:59] On the onset of a project or a provocation, understanding what our tolerance for risk is and resetting the baseline. One of the things that Toby's really good at is making sure that we're not locally maximizing at any given point in our product.

So even when we find things that work, making sure that we're not just totally locally stuck at ever hitting the ceiling. Beating an incumbent and expecting that you're going to do that on the first shot is an impossible place to put any product leader in, you know, be it from design, product data, engineering. [13:29] insane assumption, right? Any team who's had to optimize an onboarding flow and that one time you decided to redesign it, it almost always loses, right? But it's having the confidence and the agreement to begin. We're actually going out to beat the incumbent and we're going to reset a baseline that inherently, [13:47] might be a little lower than what status quo is today.

There's a great example of this that was led by Jess Erickson and our growth team in Shopify, where like the Shopify signup page... [13:59] was just this hardened thing. It's the lifeline of growth for Shopify. And so touching it, it was just such a sensitive thing. And there was this belief that like, [14:08] "Oh, some of the designs that the team were producing were absolutely beautiful, super brand for it." And there was just assumptions being thrown at this thing like, "It's not going to perform as well. It's not the right time.

We're not sure." Sure enough, we set the grounds to be able to ship that. [14:24] And it was not just net neutral, it was net positive. And it was such a great, like we've been using that story internally a lot to say like you need to create the grounds to take some risk, knowing that you're going to commit just as much iteration into the next thing as you did the incumbent product. [14:40] Can we talk about the interaction to open up the cart? [14:44] with the drawer underneath it. That's a super novel idea, right?

I don't think that I had seen that in a shopping app before. It makes total sense. I think I've actually seen it in other apps [14:52] since then. Did that have a metric story around it? How do you take that big of a bet? Because it's like, gosh, if you're not going to break one thing in a shopping app, it's like the UX of the cart, right? I know. That was a John Rundle special. One of the things, and I'll be interested to see if this sticks with us as a process going forward, but one of the things that has underpin developing shop over time is this funny thing we do called shoplifting, which is about once a year.

[15:22] but sometimes it really does where I just have this pencils down moment. I'm just scrolling shop and I'm like, we've lost our touch. We've shipped a lot of stuff. The rough edges are starting to show. The seams are starting to show. [15:35] It's time for us to have... [15:37] this moment, these two to four weeks where design just goes ham on every surface horizontally, a small group of designers saying, what could we do to make our product feel that much more special, that much more delightful and fun to use?

And out of one of those shoplift sprints, [15:55] came John's undercard, as we call it. And it's been such a signature of [16:01] the app. And as romantic as that is to say, especially in this era, I think it's something that's become a very branded part of our product. It's been wild to [16:12] watch, you know, going back to this thing about being super data driven and standard commerce experiences. I've been so floored to watch other much larger marketplaces, if I'm totally honest with you, start to change. [16:24] get inspired by what we're doing in-shop.

And most people would be annoyed by that. I think it's fantastic, largely because I'm like, well, their current scale is like quite a bit larger than ours. And so if they're deploying these ideas, that actually also means that they work. I mean, take, for example, if you hold a side-by-side up of where we landed with our very content-driven feed and where... [16:44] Amazon took their core discovery feed with these cards. Target as well. Clearly they see something in the more storytelling narrative. And that's something I'm really proud of, honestly, that we're able to take the risk and that that's it.

[16:57] inspiring the rest of the industry to make shopping more interesting for everyone, honestly. All right. Let's talk about the two to four week periods. We have the pencils down moment and maybe just even the broader philosophy behind that, because [17:09] Again, I just keep coming back to how measurable every single thing in a shopping app is, right? Metrics are king in so many ways. [17:17] And if you let metrics run wild, you probably get to Amazon, right? Like that's where all roads lead. So... [17:25] How does the emphasis on visual appeal shape the way that you as the team operate?

Can we go a little bit deeper into that part of the way that you work? [17:34] It's something we earn through having really trusted relationships with product and engineering. [17:39] It would be a very hard thing to accomplish if we just sat in our cool little [17:44] you know, design ivory tower and like [17:47] tossed down the next version of shop that we just inherently believe is right. That's not how this works. It still happens within extremely small, very talented cross-functional teams. The expectation that's set though, is that we're always trying to reach for a new bar that continually starts to rise.

And something that I'm very grateful my product counterpart, and particularly my engineering [18:17] also it really helps to be a founder-led company where the founders kind of set the stage, right? Some of the most particular directives I get from Toby are like, "Katerina, I want to open up shop and see something delightful." That's not how a lot of like CEOs talk, you know? Like it's typically, you know, I hope to see this KPI go up, I hope to see this level of user growth, [18:37] We all hope for those things, but there's just an inherent sense, well, not an inherent sense, like a real, real directive to create things of quality.

And it permeates everything we do at Shopify. I'm not saying that it's always a smooth conversation. There's negotiations that happen every day about where are we on the build? Is it ready? Is it ready? [18:56] How do we make sure that we're making the right trade-offs? Much to the chagriness of my colleagues, I'm very much a have a cake and eat it too kind of gal. I think it can be performant. [19:05] beautiful, and that we can ship quickly. Let's say Toby asked you to bring something delightful into the feed, what are the types of things that you would even reach for then?

Where does delight manifest inside of a product like this? [19:16] Yeah, well, the things we're reaching for to realize these ideas are wildly different right now. I mean, whether it be our shoplift sprints or, you know, every December, we used to sit down and say, it's time to generate like a vision. [19:28] and a moonshot for the year for shop. That's something that we've done every winter closeout period. It's kind of the thing we do before the holidays. I think that [19:36] is changing entirely. And I can talk about that in a sec, but typically what we've [19:40] thought about is just really dreaming up things.

And I would tell people in those moments, like, block off your calendar, go to your nearest shopping neighborhood, go visit some of our merchants in their real retail spaces where they've created these worlds. I mean, if you've ever been to a Skims retail location or to Kovas or Outdoor Voices, there's a whole world that they build. [19:59] And like what I've been deeply passionate about is trying to recreate the joy and the excitement of those worlds in software. Not easy to do, but to really push people to find inspiration in all matter of sorts of places.

And so it starts outside of the app and [20:16] really, really inspiring people to go find inspiration. [20:19] outside of where we usually work. I think today, what are people reaching for to render those ideas, obviously, is changing greatly. You know, talked a little bit about Luke's prototype, talked a little bit about how, oddly enough, and I think it's debate that is re-raging for a lot of designers in organizations that are building mobile products is whether to stick with [20:40] React Native or go back to Swift and Kotlin, right? I think all the colleagues I'm DMing right now are still a React house.

I'm like, oh, React Native really makes much sense anymore. [20:50] Swift and Kotlin are becoming, they're much more legible languages, there's no layer of abstractions. Agents choose to write in those things. [20:58] Design is actually now responsible for kind of pushing us in the direction of now reconsidering our commitment to React Native and working directly in Swift. And the prototyping that has come out of that and the tool building has been absolutely phenomenal. And it's unlocking creativity now. [21:16] in all manner of sorts of ways, which has been so cool to see.

And that push is just coming from the fact that designers are more empowered to raise the ceiling with Swift. [21:26] And is that something that you're seeing? How common is it for designers at shop right now to be tinkering with Swift versus simply doing static mocks, more traditional design? It's changed so much so quickly. One of the things that I think a lot of people who work in mobile design are going through this transition. But Figma has always been a mainstay as the canvas. But this transition or this tension into other tools, we've felt for a long time as many of the talented designers who came to shop introduced origami into the organization.

[21:56] origami from 12 years ago, working at Facebook, like that had been, [22:00] something that came into the organization, not a tool everybody was reaching for, the learning curve felt high. Origami is a very particular piece of software. But our dreamiest ideas usually came through the subset of designers working in origami. And a lot of people were asking themselves, other designers in shop, should I be [22:17] learning origami. [22:18] And it's at that exact moment that, like, we have this explosion of tools and our ability to work directly in code that people started to say, I mean, I could learn origami, but I'm not sure that makes a ton of sense.

Or I could not. Or I could just be working directly in the code. And one of the first, as Shopify was building up its kind of. [22:37] prototyping capabilities, it was really easy for us to spin up that world for the admin. We now have admin playground, which is the mainstay of how most of the designers work now. Might sort out a few things in the Canvas and Figma and then go directly into the admin playground, work with cloud code and develop their ideas. We didn't quite have the same environment built up.

And so designers had a bit of a wall trying to get into production code, working with React Native, [23:02] It just having a couple of layers of abstraction and the way that the code base was structured, it wasn't super legible. And so some of our designers started to basically do a transition and build a version of shop [23:14] inside of Swift that's a lot easier to work with. And we've had [23:18] incredible, like just an explosion of people now just feeling like they can jump in and work directly there. And so we've kind of had this like hop and skip over the previous leader and tool in origami.

And now people are just working directly in Swift. Yeah. [23:32] That has then led to the discussion, well... [23:35] If we want more people contributing to the code, shouldn't we be working in the most legible coding frameworks that are native to the platform, whether it be React for web? [23:44] Swift for iOS and Kotlin for Android. And that seems to be winning out. And at least in the case of Shopify, that's really been a design-led push unintentionally, just based on the prototyping tools that we've picked. And it's forcing us to come to the table with our CTO and Toby and say, I think it's time to reconsider the question around native.

And seemingly we're all bought in. And it's, as you said, just has completely raised the ceiling on designer creativity, which has been really cool to see. The fact that [24:12] that level of technical decision can actually be influenced by, [24:17] Simply wanting to get more non-engineers into the code is really interesting. That, to me, speaks... [24:24] quite loudly about where the future of work is headed. Absolutely. And I think it's a very agitating force within the organization, right? It's not like everybody's like, cool, sounds great. I posted this the other day, but it's like, Sileo keeps saying, the future belongs to designers who can build.

And I'm like, [24:41] Yes. [24:42] And those who exist in organizations that have philosophies about tech stacks and how they work. Like part of our role now is talking about the user experience of building, which is super interesting. It's a funny byproduct of us being designers who are trying to build in this new way. But I kind of love it. It's something that I think about a lot. [25:12] from what you would consider like a modern web tech stack. [25:15] And as a result, there's this... [25:17] of splintering of what the discipline of design even looks like.

Like my day-to-day looks so incredibly different than somebody who, frankly, it's not even their fault. There's just no way that they can actually work with the real code because there's so many hoops and hurdles to jump through. You know, it's just not set up for that. And... [25:34] If you are working either like in Swift for mobile, but definitely doing the typical React, Next, Tailwind, that kind of a thing, it's a runaway freight train right now in terms of what designers can do, where the very shape of our roles are just moving so much more quickly than people who don't have the ability to work in those types of tech stacks.

[25:54] Yeah. And my advice is, and this is happening at Shopify, but I think it's happening a little bit everywhere. It's easy to think about doing this inside product decks or think about doing this at startups where like there is no basis, you know. [26:06] Shopify is over 20 years old. There is a lot of legacy code. There is a lot of things to consider. There are a lot of [26:11] philosophies about front ends, back ends, all this stuff. I find some designers are exhausting themselves, like fighting those battles head to head on the principle, trying to debate with engineers directly about their technology choices.

The advice I've been giving more recently is like, [26:28] Tell you what. [26:29] refocus on what makes you as a designer differentiated, which is... [26:33] Designing what's desirable. Don't worry about visibility. Pick the tools that are going to allow you to render the idea in the most believable way. If that means you're going to spin up a web project in React, even though, you know, your team's using web components or whatever, whatever they may be using, don't let that stop your vision. [26:50] Go build the thing. The fact that you can't ship it to production doesn't mean that you've failed.

I think Max from Notion was just talking about this the other day, like not really caring if designers are shipping to production code, that it's more important that they're using the medium to be able to render the fullness of their ideas and to work with real data. That to me is what's most valuable. And so... [27:12] You know, don't worry about whether or not your thing is going to shift to production right now. That problem will start to sort itself out. And I can't wait because who doesn't want more people contributing to code safely and performantly?

I think everybody would want that. Focus on rendering your idea because [27:27] It's literally in the span of time been like a total of two hours historically that designers could productively ship to code if they didn't know code in the first place. And suddenly we went from, you know, my responsibility is to render idea to my responsibility is to like build the thing end to end. And that's where a lot of designers are actually getting stuck. Right. Where they're like, oh, my gosh, I have to like my tests are failing as I try to merge this PR and stuff.

[27:51] I get to a point where I'm like, first of all, ask yourself, is it the right scoped thing to be trying to ship to production? Are you trying to ship a full feature or are you just trying to fix some stuff? [28:00] If you're trying to prototype a full feature, [28:02] Don't go for the moonshot of end to ending this and shipping it to production. [28:06] just render the whole idea and then use that as the thing you talk to engineering with. And if they can use it, amazing. If they can teach you how to build it more usably next time, [28:16] even better.

But [28:17] That's not the expectation I'm holding for designers right now. I just want to see... [28:22] the best ideas, more ideas. That's how we build great things. Yeah, a lot of my work starts right now with asking Claude to create a route that starts with slash playground slash X, whatever it is. Unfortunately, I duplicate a lot of components and break them apart, so maybe there's a little bit of lost token use there. [28:41] it's quickly become a staple of my process. I think of that as the funny signature workbench.

It's like the old, how organized was your Figma or did you name your layers? How we reason about where our stuff is stored and why is the new mess we've all created in this work, which is fun. I was one of the very OCD Figma people. I literally taught a course about how to organize Figma files. I cared. And I had a lot of ideas about what they're... So now I'm the kind of [29:11] emergent probably in the next couple of days. And it's literally like, [29:14] the organization layer for all of my playground files.

And it's all like dated with like AI generated synopsis of like what I was exploring. And it's like this big timeline. I'm like, this feels like a new designer Enneagram test. Like you're probably also like a clean desk worker. Oh, so clean. So clean. If you're not my desk right now, you'd scream. There's one question that I can't stop asking myself. What if companies apply to talk to you [29:44] for the all new Dive Talent Network. And it's working. Like right now, I'm helping many of the most exciting startups that I know to hire the designers and builders who listen to this show.

So if you're curious what might be out there and maybe you want to get on my list or maybe you're even looking for your next design hire, head to club slash talent to join today. I want to push back on one thing that you said. I'm going to put on my design Twitter skeptic hat for a second here. [30:14] - I did. - And you talked about how [30:17] Designers. [30:18] really kind of need to ignore feasibility. [30:20] by... [30:22] Just make the thing. Don't worry about actually getting the thing in a prod, which I'm like, yes, that makes sense.

But if we take that one level further, I think you could also make the argument that the purest form of ignoring feasibility is actually not working in code. It's just throwing the quick sketch of the crazy idea that starts with what if, and you have no idea if it even makes sense to build or if it's even possible to build. [30:52] potentially capping some of the crazy ideas simply because they might be a little bit more challenging to make [30:58] real. [30:58] I'm curious if you have a take on... [31:01] I believe this was like popularized by IDEO a million years ago, but it was like their sweet spot for innovation, right?

And they talked about three things that you need to [31:12] you know, is this a thing people want? Feasibility, can we build it? Viability, is this [31:16] something that if built can help a business grow and sustain. One of the things that I've talked about in the past is that you could actually map those responsibilities to our crafts. Like designers are responsible for making it desirable, engineers determining feasibility, product managers figuring out if it's viable, right? Rough, roughly speaking. There's things that are no longer true about that and things that are still true.

[31:36] Things that are no longer true about that is that those don't cut cleanly across crafts anymore, and I think that's... [31:42] very exciting. I think what is still true about it is that design should be the tip of the spirit for desirability. [31:48] And I think that's... [31:50] probably the genesis of like, if you extrapolate that comment out to like taste, [31:55] editing, deciding what actually matters. [31:58] That's a skill set that has been naturally a home in the design practice since before computers were invented. So that has just been a longstanding thing that design has done.

I think more types of people, more types of builders will begin to do this. But... [32:13] I tend to agree with you, if you were challenging me, but I tend to agree with you that the thing that I... [32:18] hate to see, or is when constraints start driving the design process, especially now. The advice and feedback I'm typically giving to our more junior designers is they'll show up to a critique or a demo and say, here's what I thought about. And before they're telling me a story of what their vision is or walking through their prototype, they're like, [32:37] I talked to this engineer, this data isn't available.

I talked to him, you know, and we're like into a grocery shopping list of why something can happen or why what I'm being presented is like a very compromised version of the idea. That's always been an issue and always something I'm trying to coach out of people. The thing I worry about with [32:54] any new kind of tool explosion as designers are learning is that they'll start designing to their local skill set. [33:02] And I think it's really important [33:04] In theory, working with tools like HarnessLikePie or CodCode, you should be able to [33:12] break beyond those constraints.

But it's not a format that every designer is super comfortable with. There's a certain level of prompting you have to understand, you have to get your environment set up. And the thing that I keep stressing with designers is like, don't lose your idea. Like, do not lose the full fidelity of your idea. If that means right now for you, the first thing you need to do to get your brain to map it out is... [33:33] getting some screens in Figma, reasoning about your idea before you try to create a prototype.

Great. There's nothing wrong with that. But do not let constraints of your own skill sets in this moment constrain what's possible, because then I think we're just missing out on the good ideas. And that's what's important right now. I like that a lot. It reminds me of the phrase taste execution gap that... [33:53] We almost used as a way to define what design engineers brought to the table. Yes. [33:58] Even for myself, it's hard because every time that I try to build something and I push myself a little bit further, I can feel the muscle growing of front end interaction, all this kind of stuff.

And yet, [34:09] Every once in a while, I will get blocked on executing against some piece of an idea, because it's some stupid state that I just can't figure out. It's so engineering and not design, and you kind of almost have a little bit of conviction where I'm like, "Ah, man, did I just go too far in the code path here, where actually I could have got enough of the nugget of an idea to get what I need to take the next set of steps, and it could have just been doing things a little bit more traditionally in Figma, for instance."

[34:35] That's why the tool you had Marvin on a couple of weeks ago, and he talked about Artifact, this new tool that we built to kind of be the new place to share what's happening in design. It's this multi-artifact approach that actually became a very important driving force for why this thing needed to exist so that in a workspace, you can have any sort of asset, right? You can have a quick origami prototype that gets the motion transition just right. Like, would John Rundle have, like, prompted the undercard? [35:05] and it's become a signature in our app.

[35:07] I'm thrilled about it. And we built it, you know, whether it's Figma or, [35:10] a web prototype, a Swift prototype, [35:13] a video capture of an origami, whatever it is that they can all be collected in one thought space canvas of all these assets has been incredibly helpful for this exact thing so that we don't get stuck then trying to build their idea and kind of getting stuck in the in the death loop, if it were. [35:29] So we have a bunch of prototypes flying around. We have Artifact. We also have Toby who's talking about how he wants to see more delight in the app.

We have a bunch of talented designers who are just experimenting and tinkering and building their own tools. [35:42] My question then is, how do you make sure that you don't overcook this app and stuff it full of a bunch of things that in isolation are amazing things? [35:50] And yet together you have this overwhelming experience. [35:52] Editing has been an important part of the job as of recently. I'm really focusing in on what [36:00] is the most critical aspects of our experience and getting really, really disciplined about that. I think certainly that's actually a conversation we're having right now as we think about shop coming into a stage of maturity and what it is and what it can deliver.

That's been a really big piece of it. What are the primitives that really drive the most growth? [36:18] successful sessions for users. What are they coming back to? Package tracking just still really being a mainstay, the feed being a mainstay, the new innovations we're trying to drive in more of an agentic search, like those kind of being the three major things that we want to be great at. And then when we think about more broadly in shop, what it needs to be good at from a network perspective, we obviously have our other suite of products that people often don't think about when they think about shop, which is shop pay and our identity layer, getting to sign in and kind of

[36:48] shop and really everything circling around that. And [36:52] making sure that we're not crossing over into that red line of doing things for the sake of doing things and making sure that we're really disciplined. It means that like. [37:01] all of the fun things that we're doing, we're generating way more ideas now than ever, than we ever planned to ship. Whereas before we had very few, very exciting ideas that we put all our wood behind, kind of one arrow. And I think that's one of the things that's changing. And getting designers comfortable with the fact that like, [37:20] We're not going to ship everything.

But all of these things play a role in inspiring either us or other parts of Shopify, which is super exciting. [37:27] Is that what ties back to your idea about no longer doing the moonshot bets at the end of the year? [37:32] Just the pure speed and the amount of ideas that are going on. Can you talk a little bit about how that's shaped the way that you think about [37:37] roadmap sequencing, the practice of [37:40] product strategy even. Absolutely. Yeah. The idea that we like sit down in January and decide what the app's going to be next year is kind of hysterical.

Now, given how quickly we can generate ideas, what would end up happening typically is we would make that design vision. [37:55] and the first quarter roadmap would fall out of that. And we'd kind of say, which of these ideas should really shape our roadmap? What are... [38:03] you know, the backend systems that would need to exist in order to serve that kind of experience. Okay, we're going to make those investments in Q1. We've really been always design led and how we shape our roadmap. What's happening now is that that's just happening in micro doses.

[38:17] week to week where new prototypes are being generated. The one I spoke of earlier from Luke, [38:22] He made it, he was kind of like designer frazzled lost in the woods, like, I'm just cooking on all these ideas. And I'm like, this is very exciting. Can you tell a coherent story in a quick async video that we can pass around and see if people are excited about it? Sure enough, people's like, [38:36] Harold on fireman's like, oh my gosh, we're really onto something here. We zoomed him in a couple of engineers and like thinking about existing team structures and squads.

It's like, no, let's just like chase heat on this idea and see if it has legs and see if we can build it out. And so to [38:51] changed immensely. And our ability to just validate ideas is now happening so much more regularly, so much faster. Your comment on the video made me want to go down a different rabbit hole, which is obviously something like the bottom drawer is just a good idea, right? That worked and there was buy-in because it's a good idea. That exists on the spectrum, right? Not every idea is a 10 out of 10, but there are plenty of good ideas that are worth shipping, but there's [39:16] Now this challenge of like, well, you got to get kind of, you got to get people excited about it.

You got to get, there's got to be some like buy-in, some support, some heat as the word that you use. So my question then is, let's say a designer joins... [39:28] the shop team. They are now a year into it. What do you expect them to have learned about [39:35] building excitement for the ideas and, uh, [39:37] What are some of the tactics or strategies that you see of the best designers that are consistently able to rally support or even just have ideas circulate internally? I think the answer in a previous world of building wouldn't have been that controversial, but it was like,

[39:53] make a really compelling prototype and tell a story. [39:56] I think that stands now. I just think that your ability to do that, it's honestly much easier. Yeah, it's democratized. It's extremely democratized. It's a lot easier. I think for designers who start where they are from when they start to... [40:10] six months and then 12 months in. I have this story right now with a, you know, this predated our apprenticeship program, but we had Liam Fennell join us as like designer in residence. It was like, we didn't have an internship program.

So that's what I called it. And he started with us and fresh out of school, computer science degree, looking to really go deep in design. And the starting fundamentals were like, [40:30] start with small and small features, but make them [40:33] absolutely beautiful, right? And so like getting down the craft fundamentals as he's grown incredibly quickly in [40:41] deepening his skill sets as a designer, working alongside other great designers, and then adopting the tools [40:47] He's landed at the logical place I think really great designers always land, which is a hunger to shape the strategy of where shop is going.

As much as there's a really myopic focus on designers and code, which is important and true and I am totally signed on on, we're missing the other part of what this era is unlocking for designers, which is access to data, access to eligibility in the business that you didn't have before. One of the tools I lean on most often in my day as I'm talking to my agent at work is the data portal. [41:17] to say, oh, I'd never run product because I don't know SQL and I can't query my own table as well.

That went out the door. Now I can ask all matter of data questions about what our users are doing, what's working, what's not. [41:29] And that is... [41:30] one of the most helpful pieces to informing a holistic view on what we should be doing, what we should be designing. And so, you know, back to Liam, he's eight months in now or so, and he's talking to me about the fact that he really wants to be in more strategic conversations, understand why we're making certain choices, why we think something should ship versus not, because I think he has an understanding that's going to overall make him a better designer.

So that's the big shift changes. People come to do great craft work, but they leave [42:00] That to me is one of the most enduring skills in this era as we move out of like, [42:05] our central value being execution into being people who can shape great products that people love to use. [42:10] Okay, so then let's talk to a design leader who is not as innovative of a company as Shopify. There's a little bit of a lagging effect, and they're looking for what are the... [42:22] North stars that we should point at organizationally to help us keep up with everything that's happening, all of the new capabilities that AI is unlocking.

Two things that have stood out to me is you have Artifact, which I'm a big believer of. I mean, there's the whole reason I'm building a startup around it. Like, I love Artifact. The second thing is the data portal and everything that that unlocks and democratizing this access to data. Is there anything else about how... [42:46] you've seen the practice of the design shift internally that you think is, [42:52] other companies could learn from? Making internal decision-making legible. We transcribe all of our meetings. We make those accessible. We make our entire internal development process

[43:04] legible through a homegrown tool called Vault, where all decisions made on all projects can be easily documented. We have- Oh, very cool. GSD, get shit done. That's our main way of saying, here's a proposal, here's a prototype, [43:18] we've decided to build and we've decided to release. And one of the things that we're iterating on right now is like, [43:24] are there fewer steps probably based on how the process has changed. But it gives us a really clear way, both from a decision-making standpoint for [43:33] Toby to underwrite decision makers and say like, [43:36] you're going to be in the queue to just look at a couple of things coming through and say like, [43:39] yes, this should go, no, it shouldn't, this should be a proposal, this shouldn't.

And our ability to make those decisions is so important. [43:45] so much better because we have real high fidelity prototypes that we're looking at. But all of that data then has an MCP hooked up to it that as I'm looking to make decisions as a product leader, I can just ask my agent and it will query and find all of these previous decisions. We've actually worked on that before. Here's where it failed. And so [44:04] Making as much internal decision-making [44:07] legible feels... [44:09] critically, critically important. I think too, just no matter what organization you're in, great design leaders of this era just have to have a deeply intense relationship with what the business is there to do.

[44:23] and pair that intensity with a deep relationship with what makes great design. This is the combo that has, up until this point, served me pretty well. I just feel like it's so critically important to bring a deep passion and intensity to the work that's happening that you are also really deep in, because that is ultimately going to be your leverage. When designers tell you that there are [44:45] running against a wall of getting something implemented because of an engineering constraint or something in the data, you know, says otherwise. You as a design leader need to be able to zoom into those conversations and be really productive.

And it's funny for me to think about that because I think about a lot of the advice I've gotten over my career. [45:02] as a design leader that I purposely chose not to listen to. I ended up in a place where [45:07] A lot of that ended up being probably the right intuition about staying close to the work, staying close to the craft, really having a deep understanding of the business, making you like a really well-rounded decision maker that can support your team and support the business outcomes. [45:21] From a management standpoint, if we keep on the leadership trail for a second here...

[45:26] Something that I'm interested in is... [45:28] how your philosophy around what good design leadership looks like has shifted, especially given all of the... [45:36] AI-induced changes where, in many ways, like, [45:40] ICs are having outsized impact. The ability to shape strategy or the way that a team operates, I mean, there's been so much power afforded to ICs even in the last four months. [45:51] What is that like as a leader? I think it's a question on a lot of leaders' minds, and it also has people [45:57] leaving leadership to go back to being an IC, if they nurtured their craft all this time.

I certainly always describe myself as a designer, first and foremost. When anybody asks me how I design, and then if a friend's around or my wife, she's like, "Oh, I'm not going to [46:11] you like manage X amount of people. I'm like, certainly not the part that animates me in my job. What I'm animated by is trying to be a great designer. And I'm very fortunate that I get to do that alongside really, really talented people. All of them are more talented than me. Let me be clear. But coming from the craft is just really important.

I don't think that part's changed for me. [46:33] But the industry certainly caught up. I would say 10 years ago, it's getting advice to say, like, as if there was, like, some hardened path, like... [46:41] Oh, you'll have to like step away from the craft. You'll need to focus on... [46:46] the way you run a one-on-one, you'll need to really develop [46:50] this entire managerial set of skill sets that felt completely isolated from moving the product forward or helping designers design better. That always felt really foreign to me. We're at a really interesting time 10 years later where Brian Chesky is talking about this, a lot of people are talking about the fact that actually, no, staying really close to the craft is [47:12] is incredibly important.

I find it really interesting because like the guidance is like, fly at the higher altitude, work horizontally, all these things that aren't, [47:21] wrong necessarily, but I think one of the reasons why designers in shop tend to stick around a long time is I think they feel that through the culture we've built and through the way I lead, that they're becoming better designers every day by getting all to work together. And I think it's really hard to generate that culture if you're not deeply passionate about the craft. I think it'll be a really tough go in the long room for like, [47:46] the professional manager who's [47:49] Calendar is really driven by one-on-one time talking about career development.

I just don't see that being the mainstay. That's important and it can happen at a certain cadence, but one-on-one time should be about the work. Let's get into the work. Let's open up your prototype. Let's have live critique and move this work forward and help designers figure out how to make better decisions. I think right now there's a lot of discussion around, Cam talked about this a couple [48:19] building, that's the thing that we should be looking at. I think that's definitely important. It's something we've adopted. But I think- [48:24] designer's role is still figuring out the editing, right?

The critique. Why is something better than another solution? Why is everybody on this call suddenly like, "Oh, this is so cool," versus [48:35] cocking their head to side and [48:37] not really having the words to articulate it, but like, no, it's not right. It's really important that we vocalize these things and like have... [48:44] the opportunities to give critique in whatever we call those formats and however they happen, async or sync. Why is that important? Well, our material language for building is now becoming words. We now have to give critique to our agents.

Most of the time we have to point at the thing and say, "This isn't right and here's why." The higher fidelity that designers can have in the language they use, [49:06] to make their work better. [49:09] the better off they're going to be in an agentic era where they can tell agents what they want to have fixed. The broader your language, they're like, "This doesn't feel right." You're probably not going to one-shot something giving an agent feedback, and certainly designers around you aren't going to get any better. [49:24] Creating the grounds for that level of feedback to be happening feels [49:28] critically important in this moment.

[49:29] It's so obvious in retrospect, but I haven't actually thought about it that way. You're right. I give... [49:35] So much more design feedback every day now than I previously would have. [49:40] And it still feels like I'm designing, but actually, no, I'm looking at things that are not good and trying to figure out why does that not look good and what needs to happen for it to be better. [49:49] versus having me just being the one that's moving things around. And you have way less points where you kind of take a step back and evaluate your own work, where now I'm doing it like every 90 seconds.

[50:00] And we're so much more willing to because we didn't do the hard labor of pulling the thing to make the rectangle or whatever it is that we're doing. We're so much more willing. And it's actually been really funny. I've been having some conversations, some folks who are like, whether it's valued or not. Like for me, I had a classic design education, studied graphic design at university. And I still talk in a pretty traditional way. I'll talk about hierarchy, balance, symmetry, all of these like core tenets of good design that we used to talk about, you know, 30 years ago.

[50:30] who's an incredibly talented designer, mind you, like top, top, top designer, is like, [50:35] I didn't come from that background, and I feel at a loss for words these days. And the way you describe what can be improved in design, like, what should I go read? How do I, like... [50:45] re-educate myself in some of these concepts, [50:48] And I just kind of giggled. So many software designers now are self-taught, didn't come from any background in design, which is [50:55] cool and amazing, but at this time where language is becoming so fundamentally important in our process, the lack of words people have is something that they're reaching for.

[51:05] The cool thing, though, is this whole thing is recursive because I'm like, I can recommend you a bunch of books and talk to you about my design education. But you can also just ask Claude or your chosen model about how to better describe the work that you're doing and these concepts so that you can become more articulate as you give feedback. [51:22] One more thing that I want to ask you about before you go. [51:26] I kind of just want to talk to the person who is feeling... [51:30] inspired to expand their tent poles with AI and do things that maybe are outside of the traditional box of responsibilities that they've held for the last four or five years of their career or whatever.

But it's not super clear. Are there any other examples of... [51:45] app shop where [51:47] we could point to help people get a better sense of what it looks like to really capitalize on this moment in time with AI and to really push things forward or experiment or move needles that just weren't possible even a couple years ago that other people could kind of use as more tangible inspiration for their own roles. [52:07] Part of the reason why I'm at Shopify and have stayed, it'll be almost six years in the fall, is because it was a place that never put me in a box.

My career prior to this was marked by being an IC designer, then being the person who would hire other designers and eventually manage them, and then be given the responsibility of running the product. [52:26] And then spinning out of my first startup thinking I needed to go be a product manager and like went into interview loops as a product leader and then was like, these aren't my people. What am I doing? And having a total identity crisis. And then I'm saying to myself, you know what, I'm going to reshape my expectations here.

I am only going to go work at places that allow me to exercise the full spread of my capabilities to help build the right product. And I'm only going to go work at places that. [52:51] allow me to do that. And Shopify is one of those places. What's funny now, obviously, is like there's all of these discussions about