Cameron Worboys - Inside an AI-native design org

I think the biggest blockers across all of the tech industry in the next two years will not be the speed of building. It's going to be the operational side and being able to move something from like, we have built this thing. How does

it move through the operational cogs of product development in order to like get it live to customers? So my view is like, how do we set ourselves up for the new world? You have to make sure that your organization is capable at running at the same speed as the AI tools. Welcome to Dive Club. My name is Ryd and this is where designers never stop learning. Today's episode is a deep dive

into design at Cash App with their head of product design, Cam Warboys. We're gonna

get into hiring process and get a little behind the scenes of some of their recent releases to understand how the design org operates. Cam is a lot of fun to listen to, so let's dive right in. The amount of change that has happened in two years, not just a cash app, but like the industry at whole is

absolutely nuts. If you just think about it, right. It's, it's, we've had an entire

absolutely nuts. If you just think about it, right. It's, it's, we've had an entire set of tooling. We're using changing the entire speed that someone can produce a similar output has changed. The entire like organizational structure has been put into challenge. So I

think on a. good day without all of the like crazy industry stuff i think it would have been a crazy two years but then when you throw all of like the ai change on top of it it's been an absolute whirlwind but to me what i love is driving change and i think that's why i feel like i i think i'm reflecting back on two years being like i'm pretty proud of

where we've got to we've really got an insane team we've are working in a way that feels very modern. We're small and nimble and able to kind of pivot with the changes that happen every single week. And ultimately we're just producing really good work. And I think you have every right to be proud, even just digging through

work. And I think you have every right to be proud, even just digging through some of the recent, you had a pretty big release just a few months ago.

It was a big deal. And across the board, it was really high quality. So

part of my goal of this conversation is to dig into some of these modern ways of working. And I want to start with a phrase that you used last time we talked, where you talked about almost your mandate is this high quality, high velocity. So what about this big release that you just shipped at the end of

velocity. So what about this big release that you just shipped at the end of 2025, do you think shines a light on how you want this design org to operate? I think historically in product development, there used to be this insane trade-off that you could either have it of high quality and it has to be slow or you can have it fast, but then it's bad. And I think the

change that I felt the most over the last six months to a year, and even since like November, it's feels like another exponential change again, is those trade-offs no longer exist and you can move fast and you can do it with high quality. And to me, that is just exceptional. It doesn't mean it's easy to do.

quality. And to me, that is just exceptional. It doesn't mean it's easy to do.

I think that the way you achieve both of those things simultaneously is you have to run very lean teams. You have to be incredibly clear on the outcomes which those teams are trying to achieve. And then you have to make sure they're using these tools in a way that allows them to 10x output and the amount

they produce. Because I think the quality piece, there's a misconception that it comes from

they produce. Because I think the quality piece, there's a misconception that it comes from a designer sitting in some cave for three months and pontificating about the future of software. It literally doesn't. It comes from reps and the speed which you can be wrong and the speed that you can go again and experiment and experiment and experiment. And I think that's what we've seen change is the amount designers can

and experiment. And I think that's what we've seen change is the amount designers can produce has exponentially increased. And the amount of like bureaucracy and layers you need to run an organization has changed a lot as well. So you kind of package that together and it allows you to produce significantly more at really high quality, at a really high speed. And it's just like a product development dream, at least as far

as I'm concerned. So, yeah. Real quick message and then we can jump back into it. An even smarter version of Lovable just released. It is 71% better at

it. An even smarter version of Lovable just released. It is 71% better at solving complex tasks, which means it can do more work more autonomously. There's more intelligent planning, prompt queuing so you can stack requests while Lovable works. And my favorite part, there's automated testing, which means Lovable now tests your apps like a real user.

opens its own browser, navigates flows, investigates edge cases, and catches bugs for you.

And the best part is when it finds a problem, it fixes it right on the spot. I genuinely believe Lovable is the easiest way to build software today. So

the spot. I genuinely believe Lovable is the easiest way to build software today. So

head to dive.club slash Lovable to try the new release. You know what I'm excited about? The Granola MCP. It allows you to connect your AI tools directly to your

about? The Granola MCP. It allows you to connect your AI tools directly to your granola meeting notes. And as somebody who's been vibe coding a lot of tools recently, this release is a pretty big deal because my meeting notes are some of the most valuable context that I have. And now I can find specific topics, pull out action items, and get any question answered based on my meeting history. This is all

available today and I'm already building with it like crazy. So if you want to join me, head to die Now onto the episode.

Yeah, yeah, yeah. It's like a complex question, I think, that there's not one answer to. The way my brain kind of initially goes on this previously is what are the old rules, right? And if you think about the old rules, it used to be that there was this product development pod and it was an embedded

designer and it was an embedded engineer and product manager and then the pizza team essentially, right? And then you'd have a lot of these pizza teams And then because

essentially, right? And then you'd have a lot of these pizza teams And then because there were a lot of pizza teams, you'd need a lot of management layers. Then

you'd have a bunch of managers, and then those managers would also have managers, and then you'd have a bunch of structure. And before you knew it, you had this web of these giant orgs with like six management layers. Lots

of small teams and lots of people doing like micro optimization in there. And I

think what's changed from a structural standpoint is because the amount people can produce is probably like 20X, 30X, maybe even a hundred X sometime soon. You don't have to have this old model. So what you can do and what we were able to do is flatten the entire organization. So we have this rule in design, which we have a core plus free, which essentially means we're only three management layers away from

Jack. which is actually quite crazy when you think about a company of our size.

Jack. which is actually quite crazy when you think about a company of our size.

When we first decided to flatten, it was the thing that we were most nervous about. But actually, since we did it, it's been the thing that I've received the

about. But actually, since we did it, it's been the thing that I've received the most positive feedback on. And the reason is you flatten it and basically it just goes Jack, Brooke, Cam, and then the layer reports, like that's it. And what it allows us to do is not kind of like, you know, there's no hiding in various management structures. There's no game of telephone. It really just prioritizes the people who

are building the software and the product week in, week out, and then they get to skip a bunch of layers and just report up. So I think that was probably one of the most intentional things that we've done. And if you think about that, like what that actually allows you to do when you, when you kind of change the organizational structure and just flatten it, it just allows you to be much

more nimble. So when something happens in say November and we're like, oh my God,

more nimble. So when something happens in say November and we're like, oh my God, the game's changed again, we are not working through six layers of management and having to keep those five people aligned. It's a very small, tight knit group of leads where I just have one standing meeting on a Monday to keep them in sync.

And that's it. No one-on-ones, no nothing, just one meeting a week. And then the rest of our time is just spent building. And that's really what's unlocking some of these things. There's tons and tons of stuff in there, but I think if I

these things. There's tons and tons of stuff in there, but I think if I was to reflect, what's been the single biggest thing we've done that has allowed us to keep with the pace of change? It's been really challenging the traditional organizational product development structure that I think people use to deliver software at scale over the last 10 years. Can we push on that a little bit and talk about how

that impacts the practice of design or any processes, rituals? What does exist still in that more flatter org? And were there specific elements of how you all did design that you actually removed given those changes? It's interesting as well to look at the before and the after, because that's actually where it gets kind of interesting.

So we have an uncomfortable lack of process. So often some people join and more recently they've been like, whoa, this is kind of like a shock. And it's all documented, but All of our process in cash product design, I can literally picture it right now, it's about five lines of stuff. Like literally just like sentences, just like, this is like the thing you have to go to. And that to me talks

to just like the cutting we've been able to do on there. And the reason I think that's really, really important is process existed from my perspective to provide consistency and output when design started to scale and become professionalized. So,

you know, back when I first started design, I would say it wasn't really professional.

We just used to kind of wing it. We just would like kind of run on vibes mostly and like what we felt felt good. I'm sure it was probably the same with you. And then As you know, you needed design orgs to be 300, 400 people, a thousand people, you had to put any process and structure in order to support that many people. The real question, which is, has been kind of

been put into motion over the last year, two years has been of that process.

What is serving you and what isn't serving you? So we've just basically just like systematically gone through and deleted the an uncomfortable amount of stuff. Like for example, everyone is obsessed with design crits, right? And says, oh, so essential to our process.

If you actually do like a ride along of a design crit at a lot of large organizations, it's not really a strong crit in like the traditional sense. People

are just telling everyone, oh, your work's lovely. Oh, your work's so good. Maybe push

it over here. Or they like put another post-it, they put like a few post-it notes on there. And then most times like the designer leaves that career and probably ignores like 90% of the comments anyways. Right. Like you've probably experienced that. And then

it's like, well, what was the point of that? You spent an hour, you brought everyone together. So why don't we just try deleting it? Um, so you delete it

everyone together. So why don't we just try deleting it? Um, so you delete it and then you see what happens. Um, and then I think we kind of, it's just systematically gone through all of the, you know, kind of professional design processes that we've held clear and then just found a way to just like run very, very lean. So if you're a, kind of IC at Cash App, the week in, week

lean. So if you're a, kind of IC at Cash App, the week in, week out, it's pretty simple. You basically just get together and plan with your team on a Monday. And then if you get stuck, there's standing time on Wednesdays to unblock,

a Monday. And then if you get stuck, there's standing time on Wednesdays to unblock, but it's optional. You don't have to unless you're stuck. And then on Fridays, you just demo what you built. And that's like shared. So it's really, it's very bare bones, but I think it actually starts to get back to me to the pureness of product development where it didn't need to be as so complicated. And we didn't

need to have these like, checks and balances to support all of these hundreds and hundreds and thousands of connective tissue points is just getting back to building again. And

to me, that is just like the most energizing thing. And I honestly think it's what sped us up so much is just evaluating all of that stuff and seeing what serves us and what doesn't serve us. I love the two anchor points being plan and demo kind of at the bookends of the week too, because in my experience, if you do have that crit, like the formal crit, where you're actually going

to get like quote unquote approval or like get unblocked per se. A lot of times, you know, I'm guilty of just waiting. Like, I mean, I'll just wait. I'm

just going to wait three days until I can have that meeting. And then I'll just ask those two questions that I need to get answers to. And it's like, that just doesn't cut it anymore. Given like what you were talking about earlier, the speed of reps that you can do as a designer that just doesn't translate. For

me, I think the biggest blockers across all of the tech industry in the next two years will not be the speed of building. It's going to be the operational side and being able to move something from like, we have built this thing. How

does it move through the operational cogs of product development in order to like get it live to customers? So my view is like, how do we set ourselves up for the new world? You have to make sure that your organization is capable at running at the same speed as the AI tools. And these AI tools move fucking fast. They're fast. So, to me, that's an entire habit we're trying to

fast. They're fast. So, to me, that's an entire habit we're trying to change within our org around us, like the pace and the urgency that we bring into just everything. And then that means that they are keeping pace with this tooling.

And I think, to me, that puts an org in a much better state for the future. Let's talk about the Friday demos piece for a second. What does a

the future. Let's talk about the Friday demos piece for a second. What does a great Friday demo look like compared to maybe a slightly more mediocre one? The lines

between disciplines are blurring, right? Because designers now... coding staff and engineers are still coding stuff as well. And even product managers are coding stuff. So to me, a good demo, I feel happy when I've finished Fridays and I tend to pop around a lot of demos when I just feel there's been like technological breakthroughs. I can't

like say too much, but a lot of the times over the last few weeks, there's, I've been going to demos and I've been seeing what's been built and it really does feel like invention. I guess, and that we, it's not just information sharing, like, oh, here's what I built this week. That was a spec and we've fulfilled the answer in the spec. It to me feels like a, you know,

we had this challenge and this outcome, which we were trying to achieve as a group. And we were on like the fourth prototype of it. And this one almost

group. And we were on like the fourth prototype of it. And this one almost works, I guess is maybe the best definition. And it's scrappy, it's raw, but you can see like a glimmer of a technological breakthrough. So for example, Moneybot was something we launched in our full release, right? I remember seeing the first demo actually on

web of Moneybot, where we basically took a customer's data and like art some of our data, we're able to like feed it into this thing and have a response back. And it was probably, the design was not good. The execution was so slow,

back. And it was probably, the design was not good. The execution was so slow, it took so far to pin it back. But it was the first moment where you could see all the potential and you were like, oh, wow, we're like having breakthroughs here. In a good week on week basis from demos, those breakthroughs tend to

breakthroughs here. In a good week on week basis from demos, those breakthroughs tend to like compound and then that energy just like filters into the team. And then I've at least seen people want to keep like leveling up on those like breakthroughs, which they're having in demos. So there's, there's no like formula per se, other than just show us what you built this week. If you built something incredibly complex that's really

hard and you've broken through, great. If you've just built something that's raw or if you're just doing animations for the week and final mile polish, that's absolutely fine. It's

just show us what you've made this week. I think Moneybot's a pretty interesting thing to look at because so much of what makes it special exists outside of the pixels. A lot of the design even is outside of the pixels. So maybe we

pixels. A lot of the design even is outside of the pixels. So maybe we could even use that as an example to talk about how the value prop of design has shifted at Cash App. both maybe due to the type of product that you're working on, like a money bot, but also it sounds like people are experimenting more with these tools. You talked about the value of technological breakthroughs, more people are

coding. What has that shift looked like in practice at Cash App? Almost all of

coding. What has that shift looked like in practice at Cash App? Almost all of our products and I know it goes now like shipping PRs. And I found it kind of funny. I can pull it. The data from my top of my head is like over 90%. It's like kind of crazy. It's a big deal. Yeah, it's

a big deal. But what's funny is designers keep gravitating towards the most designery stuff. And I found, a lot of designers are fixing these small refinements in

stuff. And I found, a lot of designers are fixing these small refinements in the product that have bugged them for years. And it's just been like a funny course of action. It's like, you get keys to the kingdom and you can ship these insane things. And then designers are like, oh, this pixelation on this screen was really awful. The amount of key line alignment I've seen. We used to have some

really awful. The amount of key line alignment I've seen. We used to have some issues in our app where there was quality of some pages would be like, and things just weren't quite perfect page to page. And there's two designers I'm thinking off in the top of my head who are just like smashing through PRs. And Lauren

has this phrase called like the pixel janitors. And they are like the pixel janitors who are just like going around cleaning up after our developers who like didn't make the app completely pixel perfect. So I know that's a tangent of the question, but I think that's just an anecdote, which I'm finding so funny. But I think over time, it will start being pixel janitors and designers shipping code. And then confidence will

just grow from there and grow and grow. And I do see a world in the not too distant future where very complex features are being shipped via just a builder. And you can't distinguish whether that builder is an engineer or a designer or someone else in a discipline. they're just able to visualize and invent

something and to ship that through these tools. So that's where I can see it going. I just think it's going to slowly be like a progression and then we'll

going. I just think it's going to slowly be like a progression and then we'll wake up one day and it will be like, wait, there's no more roles. It's

just who can ship good stuff. And I can really see that trajectory already happening.

I'm feeling that a little bit, even for my own practice, like I've made a couple of PRs in the last few days where I'm like, I just honestly step back and I can't believe it. I cannot believe that I did that. You know,

it's so... the line of the P3 polish ticket. That being said, for you to even get close to that at an org that's so much bigger, and if you're even close to this 90% number, that's a pretty incredible feat. So Has

there been any top-down investment or anything that you're doing to help designers get more comfortable in code? Is it just happening organically? How have you been able to see such an organizational transformation over such a short period of time? I think we've been far ahead in the tooling aspect that enables designers to do this. So we've had a group of people who essentially look at the AI enablement side of it, and

there's an entire program that's dedicated to code fluency. And that's helping designers from zero where they don't have a GitHub account all the way to like shipping a PR into prod. The first stage starts in like a sandbox PR. So you

can kind of mess about. And then, um, once people have kind of got comfortable shipping inside the sandbox, we move into like the actual product. And then there we found some engineering pairing is like really helpful just to help designers Honestly, just like navigate it. Like, I don't think it's necessarily building the code, which is the hard

navigate it. Like, I don't think it's necessarily building the code, which is the hard part. anymore. It's more so which buttons do I press and the world doesn't end.

part. anymore. It's more so which buttons do I press and the world doesn't end.

So true. So you're just like there and you're like, okay, I'm not like a technical, but you know, I'm not technical in the sense of like a development and you like read some of these things and just even the file names, you're like, what is this? Every button in GitHub is scary too. Like even the squash and merge, like I looked at that and I'm like, it's green. Green normally means like

it's okay to press on, but I'm like, Now I got to Google this. And

I'm like, I'm searching. I'm like, do I hit the squash and merge button? It's

very clearly the only button on the entire page to hit. But I still couldn't get myself to hit it. Yeah, that sounds about right. I think by the end of Q1, we'll be 100%. We've got a few people who are obviously out of office and stuff like that. But we'll have every single designer have shipped production PRs by the end of the course, I think. world is changing. It's one part of

it though. Like I think, you know, there's still the building part, but there's still

it though. Like I think, you know, there's still the building part, but there's still these other jobs that happen in this new world that to me are just like, just as essential and even more important in this new world as well. You want

to go a little bit deeper there? We basically have a DRI concept That stands for like directly responsible individuals and the DRIs are responsible for needing a large group of ICs to achieve an outcome. And what's really interesting from my perspective on that, right? If you actually think about it is there's so much

stuff you could do. The real challenge then becomes if I've got this infinite set of options, like what is the strategy and how do we coalesce a large group of builders to deliver on that strategy fast so that we win. Like that's an art form in itself that I think is just as

we win. Like that's an art form in itself that I think is just as critical. Cause otherwise what you'll end up with is you'll end up just so much

critical. Cause otherwise what you'll end up with is you'll end up just so much shipping. It won't click together. It will be, you know, one part of the org's

shipping. It won't click together. It will be, you know, one part of the org's going over here, another part of the org's going over here. So these tools are amazing at increasing the amount of output But output without that taste and that ability to be like, this is where we're going strategically as a company. And these are the people who are going to help drive us week in, week out towards that

direction. And that to me is just as critical as the people who are, you

direction. And that to me is just as critical as the people who are, you know, shipping the code and building it day to day. And I think design also has an opportunity to really, from my perspective, like step into that role because design can visualize what the future could look like. A lot of other skill sets

can't do that, right? Like people have to write documents or something like that. But,

you know, if we're trying to go after, say, the next version of Moneybot and talk about it in the future, a designer can actually prototype something, show it to everyone and be like, this is the direction we can go. And then everyone's like, yes, let's follow that, right? And that allows this group of builders to essentially know where the flagpole is. So maybe a good way of articulating it is I think

as the output increases, the value of clarity of vision just becomes more and more important. Because otherwise you end up in this jack of all traits, master of none

important. Because otherwise you end up in this jack of all traits, master of none software, I think. Maybe we could even tie a bow on everything that we're talking about here. Because I'm sure some people listening are excited by all of the change,

about here. Because I'm sure some people listening are excited by all of the change, but also people are trying to figure out almost like career strategy, you know, like what's the North star that I want to even point myself at in terms of what I want to bring to the table. One, two, three, four years from now to continue practicing as a professional designer. So when you think about maybe even like

the archetypes of designers that are having real success in your, or where do you kind of draw the lines? Like where can somebody point at or the decision matrix of what type of designer do I want to be where I could When you're in these periods of rapid change, the most important thing is being malleable and then being able to reinvent yourself again and again and again at the pace

of change. So if I was to give any advice on like long term career

of change. So if I was to give any advice on like long term career longevity is I'd say there is no fighting this direction of travel, right? It is

fundamentally changing the entire product development process. So retooling is a lot of people who are not a luxury, it's like a must do. And I think it's going to be, if you're not AI fluent in, I think you will struggle to get a job, to be honest, in the, in the not too distant future. You might even struggle now. I was about to say, we might be there already. I think, I

struggle now. I was about to say, we might be there already. I think, I think so. It's sad to say, but I think it's just like the truth. And

think so. It's sad to say, but I think it's just like the truth. And

then I think as far as like the evolving shape of it, I honestly don't know, but there's, there's three archetypes, which we're working towards. And I think at the highest level, it's a world where the lines between roles are a lot more fluid.

And we basically talk internally at Block and I can't take credit for this, but there's basically a DRI is the person who's driving the work. There's ICs who are the craft makers, the tastemakers driving the actual execution towards that goal. And then there's player coaches, which are like the leadership layer of the organization. I can like go into each one of those, I guess, from, I think a DRI is, is a

really interesting thing to lean into, particularly as a designer, because Your strength as a DRI is essentially is your ability to take a loose strategic nugget as a business, right? So for example, at the moment, I'm very focused on this idea called neighborhoods, which is how we connect both sides of the counter between Square and Cash App. And if you think about that, that's like, it's fascinating problem to

solve. Why, when you walk into every single Square shop, should you not pay with

solve. Why, when you walk into every single Square shop, should you not pay with Cash App? There's no reason, right? And it's like a, very technically

Cash App? There's no reason, right? And it's like a, very technically interesting challenge to solve, but also very customer-centric experience challenge to solve. That's like an important role, which I think shapes the future of design. It's like people who can take maybe a good way to frame it as like creative problem solving and start to think about what are the biggest problems that this business faces and how can

I use building and product development and design thinking to help people visualize and follow me on that change. Like that's a role, which I think will still be really important. And then on the IC side, the ICs that are thriving at the

really important. And then on the IC side, the ICs that are thriving at the moment are what I would just call like just builders. They are people who bias towards action. They are very outcome focused and solution focused

towards action. They are very outcome focused and solution focused versus linear process focus. They're just like, okay, cool. We're going to connect both sides of the counter through Square and Cash App. Let's just start building some prototypes of how we could potentially do that, get that into customers' hands. They're not

scared of being wrong. I think that's probably the most important trait that I'm seeing is that ICs who are willing to be like, I back this as the first direction is actually an undervalued skill. And I think those ICs tend to be really, really thriving at the moment. And then in the player coach space, there's still a...

a deep need for leaders in design. But we did this before the AI push, but we've, we don't believe in like professional managers in the sense that other large tech companies might have. The idea to me that you have a manager who is not responsible for the output of their team is just like one of the dumbest things in the world and just doesn't compete with me. And so our managers are,

or our leads, we call them our player coaches. They are responsible for driving outcomes and positive outcomes in the team and all of the pixels, which they're pushing and their team is pushing. They are responsible for. So those are the three archetypes, which we have. And I think across those archetypes, you're almost seeing like different skills prevail.

we have. And I think across those archetypes, you're almost seeing like different skills prevail.

And, you know, I would summarize it as like the DRIs are like the people who are able to kind of do like creative leadership, essentially. Um, the ICs are just the builders who just produce and create amazing high craft outputs. And then the player coaches are essentially the people who can kind of lead the ICs towards achieving great outcomes. And that's generally what I've seen, but maybe the inverse of that would

great outcomes. And that's generally what I've seen, but maybe the inverse of that would be, I don't think the kind of middle professional management layer who doesn't actually produce stuff will exist. I don't think it exists anymore, perhaps in the way it did three years ago. I remember interviewing at a big company and they're like, do you want to be an IC or a manager? And I was like, Can I be

both? And they're like, no, no, no. And then people would have invested like five

both? And they're like, no, no, no. And then people would have invested like five years of their career in just being a pure play manager. And then they're kind of locked now. It's tough. It's tough. I genuinely feel for those people. And I

really like DRI a lot because I think it's been easy to evaluate where you want to grow as a designer on kind of the engineering product triad a little bit. It's like, oh, do I want to go down the code path more? Do I want to go down the product path? And product... felt like a

more? Do I want to go down the product path? And product... felt like a departure from design in some ways, but it's so clear that there's this need on the strategy. You said creative problem solving. I love that. It's like AI is accelerating

the strategy. You said creative problem solving. I love that. It's like AI is accelerating everything. It's like, great. The bottleneck in some ways is ideas. You've got to come

everything. It's like, great. The bottleneck in some ways is ideas. You've got to come up with things and direct things. And I totally believe that designers might be the best positioned person to to thrive in that role. Yeah, I feel similar. Being the

ideas guy always used to be like a joke, right? Yeah. And now like actually it might be valuable. It was such an insult like 18 months ago on Twitter and now it's like, wow, we need more ideas guys. Hey, we're hiring ideas guys soon. Yeah, yeah. Maybe it's different though. It's like the most successful DRIs, like I'm

soon. Yeah, yeah. Maybe it's different though. It's like the most successful DRIs, like I'm thinking of Brian and Owen, they're super senior people in the company. They're DRIs as well. And obviously Brian was like the old CEO of Cash Apps. He's like the

well. And obviously Brian was like the old CEO of Cash Apps. He's like the perfect definition of a TRI because he could just make stuff happen and think strategically.

But it's a really fascinating thing because you do need more of those people at different layers. And you have to build a bench of highly capable leaders who can

different layers. And you have to build a bench of highly capable leaders who can essentially lead the robots plus the humans to deliver these outcomes.

And I don't think it's as simple as people realize. And I've definitely seen, even through friends or even from personal experience at Cash App, where If you have just like a bunch of people building stuff and making stuff, but it's not being shaped into like a coherent direction and strategy with taste and curation, it kind of just feels a bit rudderless and you're like producing stuff, but it's not really driving the

impact. And that to me is perhaps one bit which the industry at large is

impact. And that to me is perhaps one bit which the industry at large is maybe not talking about, because you can make stuff and build stuff all day, but if customers don't want it, it's kind of pointless, right? There's one question that I can't stop asking myself. What if companies apply to talk to you rather than the other way around? And that question is the foundation for the all new Dive Talent

Network. And it's working. Like right now, I'm helping many of the most exciting startups

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 dive.club

slash talent to join today. So we're talking a lot about archetypes and everything that's changing in the world. My question then is, how's this influencing the way that you're thinking about hiring? And maybe even like the signals that you're prioritizing and evaluating people and trying to figure out who's the best fit to bring into the

team. So I think the thing that's universal and has never, ever changed is someone

team. So I think the thing that's universal and has never, ever changed is someone a good designer. And that might sound stupid, right? When I say that out loud, but most designers, I think the other stuff that

surrounds craft is much easier to teach, but someone's innate eye is a lot easier to teach. And taste is actually the most valuable thing that I think I've time and time again had. Like there's a lot of people I'm thinking of who you could just tell they had an eye for it and they hadn't necessarily had the opportunity. And then you give them the opportunity and then the eye

prevails. And to me, like the eye implies that it's just this like visual only

prevails. And to me, like the eye implies that it's just this like visual only thing. And it's not, you know, when you look at a product and it just

thing. And it's not, you know, when you look at a product and it just feels right. And they've balanced it and it just feels like incredibly obvious. That's a

feels right. And they've balanced it and it just feels like incredibly obvious. That's a

really hard value to place on something. But I think it's actually probably the single most important skill as like a designer. And I think as the number, as like the amount of output you can produce comes up, we're going to see a ton of slop. And then we will see a smaller and smaller amount of designers and

of slop. And then we will see a smaller and smaller amount of designers and people who can really just like select with such intention and focus that They know what good looks like. So to me, that's like the universal trait that hasn't changed, like craft, taste, whatever you want to call it. And there's a misconception that it's just like the visual side. It's not just the visual side. It's like, it's the

combo of it all and it just feeling right. Like that's, that's really, really important.

And then I think the other stuff that we've seen change more on the hiring side is just general AI fluency and stuff like that is just kind of a given now. I think it's unlikely that you'd get through the interview process if you

given now. I think it's unlikely that you'd get through the interview process if you weren't building some stuff in AI and like had other projects. There's some people, for example, who work at companies who aren't as AI forward, but have insane craft levels.

They tend to be like, oh, the weekends I built this amazing tool and you can kind of connect two and two and you're like, this is enough. So I

don't know if that answered the question, but I think the most important thing to say there is craft always shines through. And now more than ever, even if you look on Twitter and you see the people who are like growing their followings exponentially as like an IC, it's craft. Like they're building amazing prototypes, they're building amazing interactions.

And I just don't think that's disappearing anytime soon. So that's what I keep looking out for. And that's what a lot of people at Cash App and I think

out for. And that's what a lot of people at Cash App and I think that's why the fit and finish of the app feels quite nice because we have a lot of people who care deeply about that stuff. I want to drill into the AI fluency piece a little bit. And I want to speak to a very specific listener who hears you. Maybe they've actually been kind of hunting all the AI

stuff because it's annoying and they don't have time for it. And you just convince them. You're like, all right, shoot. I actually really have to invest in this. But

them. You're like, all right, shoot. I actually really have to invest in this. But

it's unclear. Where is the threshold? Like what line are you trying to see designers get over where you can say, yep, they have what it takes and they've experimented enough or they've built enough. So if you're an IC and you're a builder type, I would guess, and I may be wrong, if you're asking yourself that question, you're probably not a builder. Because anyone I know who is thriving in this

builder-first icy world, they are so emotionally enthralled by this change that is happening because design was always gated behind technical expertise and it was always like you needed someone else to realize your vision. A

lot of people I know who are interviewing and or work at Cash and Block and everywhere, They are shipping fun things on the side just to experiment and have fun with the technology. And that is, for me, from an IC perspective, that is a builder. And they bias towards action. They love making. If they have half an

a builder. And they bias towards action. They love making. If they have half an hour free, they're going to tinker on something there. I guess that's a way to probably challenge the question a little bit. If you're asking yourself that, I think maybe the better question is, can you compete? with these people who are high craft, high

taste and building at incredibly high velocity and like figures spread to mind. And honestly,

I would say if you can't, like don't get in the game because it's probably not worth it. You're not going to have a gig. It's a good answer. Honestly,

I respect the pushback because building is pure love of the game at this point.

It's like, like you said, like we've, as an industry, we've almost like had this coiling of man, it'd be nice to build my ideas. And then all of a sudden it was like, boom, and now you can. And it's just like, okay, cool.

This one, this one, this one, this one. That's tough to compete with. If it

doesn't come naturally and you're not excited about it, it's tough to compete with. So

then, then what? There's other things, right? So like, you know, in a leadership role and in some of the other archetypes which you're looking at, then the skill set is more so like, how do I... shape an organization and shape strategic direction for these ICs who are producing this insane amount of stuff. Like

that's the skill set in itself. There's no like course on that, I don't think.

And if there is, you know, someone's probably making a lot of money. I think

that's a skill set that's incredibly valuable in this world. It's like creative leadership or, you know, I don't know what the answer is in exactly how to define that, but that's maybe a space which people I think could go into if in this world, but it's going to be harder. Like that's the honest truth. Design jobs, I think were, plentiful and everyone needed design. And I think what you're going to see

is there'll be fewer gigs because people can achieve more with less. And that to me just means the standard gets higher and what people have to produce. So I

just see the quality of people getting better and better. So I think it's also really important to like caveat that in this time that I think the design industry at large got really guilty of overvaluing people's resumes on a logo.

And I transparently like don't give a shit about where someone worked. He'll

probably kill me for saying this, but like one of our best designers hands down, and I think he'll come on to be like one of the best ICs in the company. His job before was like work designing stuff for Yo Sushi. No shade

the company. His job before was like work designing stuff for Yo Sushi. No shade

at Yo Sushi is cool, but it's not like the Airbnb or like meta of the world. And I think it just comes back to raw talent shines through. And

the world. And I think it just comes back to raw talent shines through. And

raw craft and raw skills shine through. So for the ICs of tomorrow, I think you'll just see them bubbling up. And we had this, like, we had these builder fellows joined recently who are like, like no college, fresh end to working with us.

And the amount of, like the skills which they have, they're just like Swiss Army knives. It's terrifying. They can literally do it all. So yeah, I know that's like

knives. It's terrifying. They can literally do it all. So yeah, I know that's like a bit of a long-winded thing, but I do think it's important for us as like design leaders in this new world to not be overly attached to resume logos and all of that kind of bullshit that's actually with it and just look at raw skills of someone building and transparency from my side and i know

i speak for all the blocks that we don't care where someone works we don't care where someone lives it's just like do you have the appetite to work in this high velocity high craft environment and do you have good taste and could pull it off so hopefully that changes but again i thought that was an important psa to say no i think it's great i'm glad you said it because there's a

lot of reasons to be intimidated about the future but That is the reason to be optimistic. Like this is the great leveling of the playing field. Literally just today

be optimistic. Like this is the great leveling of the playing field. Literally just today we released an episode with this guy who just landed a really cool founding designer role through the talent network and his resume sucked.

He wouldn't even feel bad about me saying it. Like he, he didn't like the company he was at. It was very low craft. And he just went out and made a baller portfolio and a really cool side project and sweat a bunch of details on his portfolio site. And it was more than enough for me. Like, okay,

this guy's really good. What the heck? This guy's a gem. And he will fly past people who, you know, dare I say, maybe have spent the last five years at Meta on a tiny little slice of the product because he's like this generalist that AI is accelerating in every single direction. That archetype, so, so exciting. And for

the first time in a few years, probably like this is, their moment. Like if

you are that person, this is your time right now. I've recently joined Twitter again and I like DM quite a lot of people where I just, their work pops up. I'm like, their work is sick. And I don't look at their LinkedIn. I

up. I'm like, their work is sick. And I don't look at their LinkedIn. I

don't, it's just like, you know, let's chat and people will get jobs off the back of that. And it's not saying, you know, you have to post all your stuff all the time, but it's just, and it, and it just, I don't know.

I just think you just see Kraft cutting through a rate that it didn't before.

And previously perhaps, You know, you would go to a large tech company and there would be like 10 rounds of interviews and everyone would be like, tell us about this, tell us about this. And it was easier to get into the CIA than some large tech company interviews. Whereas now it's just like, show us what you built.

And I absolutely love what feels to me like the smashing down of the last 10 years where design became bureaucratic, overly professionalized, And now it feels like we're getting back to basics. And that to me is just so energizing. And that's probably why I'm so hyped at the moment at work.

I want to return back to something that you said earlier. And you were talking about the connection between cash and Square. Yeah, neighborhoods.

Yeah. And there was a tweet that I had circled that you put out, I don't remember, a couple of weeks ago, where you just talked about how something you're thinking a lot about is creating a shared platform. DNA, like visual DNA, even between Square and Cache. That's not a small project or initiative to lead given the scale that we're operating at. So can you just shine a light on some of the

things that you're thinking through on that front? It's not just like changing design language for changing design language. That's like the best way to phrase it. If you think about that problem, which I talked about earlier of like connecting both sides of the counter, there is a customer experience and like design language part to it that What works about the Apple devices when you go from an iPhone to an iPad to

a TV is there's this feeling of similarity, even though they're different OS's and core experiences that make these handoffs feel very seamless. A while ago, because Cash App and Square were pretty separate until we functionalized the company, there was no incentive to think about how that connected. So they were, by and large, separate things. So if

you had designed this very smooth handoff at that time, it would have felt like you were handing off between Toast to Venmo, right? Because it's two separate companies.

So actually, Square and Cash App are a single company, and we're going to connect to them, and it's going to be one of the coolest things ever. But we

need to make sure from a customer standpoint that the experience feels seamless. The

obvious answer there is, oh, let's just make them both the same. Let's just make Cash App and Square have the same design languages, have the same systems. But then if you really interrogate that, it's like, oh, wait, Cash App is like one of the most crazy, culturally relevant brands that appeals to like a very young generation. We've

got 25% of US teams. And then Square is like a hardcore working B2B software where people are in the app for like eight hours a day. So if

we start like, you know, dropping crazy illustrations and tons of white space everywhere, we might you know, people might get annoyed. So what we started talking about as a group is like, well, how do you connect them? And I think this is where it comes down to that deeper layer of like strategic drivers. And this is something that Lauren was involved in and deeply passionate about is actually design runs deeper than

that. And you can start to think about what we call shared DNA and this

that. And you can start to think about what we call shared DNA and this idea that it's siblings, not twins. And if you think about that as the analogy, what we're saying is there is shared foundations that make it feel like it's a block designed product, whether that's tight, some shared like base tokens approach to the grid.

And then there are these unique personalities that get put on top of it that allow each of the brands to shine, but also make that handover moment not feel like you're jumping between two different companies. So that's, I guess, why it's interesting because it really is like design as a strategic asset because you're using design to solve a customer problem and to solve a business problem, which is how do you connect

both sides of the counter. One of the personality glimpses that I really liked from the latest release was these personalized payment pages. Can you just give us the backstory there? Like how does a project like that come up, get greenlit, be brought to

there? Like how does a project like that come up, get greenlit, be brought to life? Like what does it take to pull something like that off? Because it definitely

life? Like what does it take to pull something like that off? Because it definitely exists so far outside of the traditional box of responsibilities that a lot of designers, especially people working on B2B, get to even sniff. That's like a personal one. I

still think we can take it even further. Again, it just goes back to that like creative problem solving again, right? Most payments, essentially, like moving money between you and I, it's become a commodity. So the prompt there is... How do you start to make the experience of moving money between you and I feel less commoditized?

And if you and I were just now to ideate on that, you'd probably say, oh, well, what if you could send a special message? And then you're like, okay, cool. So what we did is we actually looked at the messages that people were

cool. So what we did is we actually looked at the messages that people were sending in their payment notes. We pulled a list and aggregated it. Again, using AI, we're able to look at millions and millions of payment notes and find out why people are moving money. And you see there's a lot of things that are kind of functional, right? So like rent, you know, no one's celebrating rent. But you also

see there was a lot of very emotional things. Like, for example, graduation, birthdays, dinners for a special reason, right? And then you kind of pull that thread and you're like, why shouldn't that experience be more than just this, like, sad utilitarian thing? And it shouldn't. So we were like, let's design a bunch of, custom

thing? And it shouldn't. So we were like, let's design a bunch of, custom assets that mirror all of these moments that people are sending money. And that's where we started to like see if it worked and see if customers are loving it.

Customers do love it. They're like big advocates for it. And I think we will continue to push this idea that it's completely personalized and moving money doesn't need to be this like commodity for the rest of the year. A lot of the things that you're talking about, related to maybe finding the shared DNA, you know, people translate more into this like design systems bucket. I know Lauren is leading that doing a

great job there. And yet much of what comes out of cash specifically is like, frankly, bizarre, you know, it's just very, very different. Can you talk a little bit about like that tension? Like how do both of those things operate at a high level where you have this, you know, the systems required for craft at scale while also trying to be deeply creative in the core brand and what that expression

looks like. It's like one of the most existential challenges that I think every tech

looks like. It's like one of the most existential challenges that I think every tech company should be thinking about deeply right now. I think it's better to be on the side of expressive and unique to customers so that they have an emotional attachment to your product versus like, you know, consistent

and essentially like, you know, commoditized. Yeah, vibe-codable. Vibe-codable, yeah. Like, that's

genuinely. So, for example, one of my favorite apps that I didn't design at the moment that is out there is like Bump. I don't know if you've used Bump.

It's like MapApp. And I met the designer and he's like, yeah, we just YOLO anything. It's just like, how weird can we make it? Friday's episode is with Julian

anything. It's just like, how weird can we make it? Friday's episode is with Julian Martin. Oh, no way. That's so funny. Yeah, well, mad respects. I think that that's

Martin. Oh, no way. That's so funny. Yeah, well, mad respects. I think that that's a good example of like, I just think you have to. And we're definitely forcing ourselves to get out of our comfort zones. I guess it's maybe the light way to describe it because the traditional logic was, oh, consistency is ruthlessly adhering to this very strict design system was the only way to adhere consistency. Right?

That was like the truth for a while. And I don't think that is necessarily true. Like design systems have to be able to flex and allow for more expression.

true. Like design systems have to be able to flex and allow for more expression.

And then I think if I put the new age layer on it, I believe One of the primary ways which you will create lock-in in the new world is creating apps that feel completely one of one. So what I talk a lot about Cash App is I want in six months, a year, I want everyone who's sitting at a dinner table to open their Cash Apps and put them on the table

and every single one looks different. It's a complete expression of their personal identity. And

if you think about it, like we actually have the heritage of doing that. We

have our cards, right? You've probably seen the crew debit cards. You can customize them, you can draw on them. And actually when you think about the future of software development and where it's going with generative UI, there is nothing in the future that's going to prevent us from creating these completely one-of-one experiences. So

that's what like is top of mind for me at the moment. And I do think we will get there relatively quickly that every cash app does feel unique and completely designed around the person. And then from a business perspective, why I think that's super interesting is it creates this like deeper, harder to quantify emotional connection with a product that is the same as like your wardrobe. Clothes are by

and large like an expression of personal identity. We've seen a trend, particularly in younger audiences, that digital identity is as valuable as physical identity. You just need to look at the Fortnite store to see the numbers there. So, you know, I think from my side, I have a very deep belief and a bet that, interfaces in the not too distant future will be bespoke completely one of one. And at least in

Cash App's instance, a complete representation of your personal identity. I mean, like my brain is already running like, how applicable is this to B2B? You know, like how far are we going to go into this? It's so applicable. I think it is. So

my dad, he still runs a tiny little small business antique shop, right? And his

options previously were he could have his own middle website, which was so difficult for him to manage. Like he's not a technological guy, he's an antique dealer for God's sake, right? Like you can kind of picture it, right? Or he could upload to

sake, right? Like you can kind of picture it, right? Or he could upload to his antiques to like some big conglomerate that standardizes the experience and his like personal touch and his shop and like all of the effort he puts into it basically just goes into like this commoditized like DoorDash-esque platform. Like that to me is just like not the future of B2B software. Like, you know, if my dad was

able to create a completely bespoke, you know, solution and piece of software that allowed him to serve his customers and create a website that was a representation of his style and identity, it would have changed his entire course of his business, but he wasn't able to do that. And I genuinely think in the future that people will be able to do that. And even at Square, we're talking with lots of customers

at the moment and building stuff, and you can kind of see the direction of travel, but People want very bespoke interfaces as much for B2B because every restaurant is different. And I just think that's like one of the biggest opportunities ahead for design in general, which is like, how do you make this stuff? And then

how do you make sure it comes together in a cohesive way? Creativity as a competitive advantage, regardless of industry, does feel like it's going to become more of a thing, which that's exciting as a designer, you know? Because if your product doesn't have something that obviously there's this bucket of top-down enterprise contracts that are always going to exist. But there is an abundance of choice, and one of the choices is make

exist. But there is an abundance of choice, and one of the choices is make it yourself. So it's got to be good. In the same way that you were

it yourself. So it's got to be good. In the same way that you were talking about the bar is rising for designers, it also is going to rise for products, specifically SaaS, probably. I hope so. Maybe I'm wrong. I really, really hope so.

I just think software was... You had to mass produce it previously, essentially. And

it had to be one size fits all for almost every customer. And if you were in work day and signing a contract for like 10 million, you probably got some customization to it, but by and large, it's like the same product. And I

just think that whole notion of how software is created is kind of being challenged.

And that to me is just so energizing. If I didn't believe that creativity had a role in this new world, I would quit my job and give up. And

my wife's an amazing baker. I would just support her doing like bakery. honestly but

i genuinely believe that the world would be a better place if more businesses really led with creativity and used it as a tool to drive the outcomes at scale and that's really what fires me up personally it's you know there's very few i know like the designer founder trope there's very few designer founders there's

very few designers on boards and i think design is often misconceived as just pixel pushing and it's not, it's like creative problem solving. The design industry at large can look at problems in a very different way and come at them in a very different way. And that's like a skillset that transparently I think would make the world

different way. And that's like a skillset that transparently I think would make the world a much better place than today where it's like, you know, just giant conglomerates in every shopping mall and like not enough neighborhood businesses thriving and, uh, you know, one size fits all software and mass produced clones. Like I think there's an opportunity here generally. not to go too philosophical, is for design to push

against that tide of the last 10 years, that it's all conglomerates and go back towards more of creativity at the heart of everything, neighborhood businesses, neighborhood stuff.

And I think that's very, very energizing to me. I saw someone on Twitter, I think actually it was last night, refer to this as the niche economy, and I'm totally adopting it because I think that it's so relevant for designers because even if we were able to correctly identify a problem, which as a whole, given the population, we're pretty good at, right? Like that's what we do. It didn't really matter because

there was still such an upfront cost and skill gap to actually be able to go and solve the problem where all of a sudden now it's token cost and the time cost is driven down. We are not reliant on other people to actually go and solve the problem. So I do hope that there are so many things design created businesses that don't necessarily have to be these billion dollar companies. It doesn't

matter, right? It's the niche economy. I think the niche economy can be driven by designers and I'm very excited about the future for that. I love that phrase. And

it's almost like we were saying earlier, before we kind of press record, I was talking about the I think future tech companies might be like CPGs and it's not dissimilar to that where it's like, actually, is it one piece of software in five years time that serves a billion people like Meta does, or is it split up into 30 pieces of software that solve much smaller niches? So you go to... know

your fitness app is booked here like your local community is just your where you live but that to me feels like a much more competitive and better world which i hope exists but it also could just not and get eaten but by these big ai companies but yeah i think for the good of the world it would be amazing if it went this way and i hope design continues to have a

role in shaping it to be honest canvas has been incredibly energizing i appreciate you coming on today and given me a lot to think about and also just learning more about how you all operate and everything that's going on has been just fascinating.

So thanks for coming on, pulling back the curtain, talking with us today. I really

appreciate it and thanks for listening and I hope it was enjoyable for you guys.

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

during crit. Jitter is how I animate my designs. Lovable is how I build my ideas in code. Mobbin is how I find design inspiration. Paper is how I design like a creative. And Raycast is my shortcut every step of the way. 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 partners.