Cameron Worboys - Inside an AI-native design org

00:00:00I think the biggest blockers across allof the tech industry in the next 2 yearswill not be the speed of building. It'sgoing to be the operational side andbeing able to move something from likewe have built this thing, how does itmove through the operational cogs ofproduct development in order to like getit live to customers. So my view is likehow do we set ourselves up for the newworld? You have to make sure that yourorganization is capable at running atthe same speed as the [music] AI tools.Welcome to Design Club. My name is Ridand this is where designers never stoplearning.Today's episode is a deep dive intodesign at Cash App with their head ofproduct design Cam Warboys. We're goingto get into hiring process and get alittle behind the scenes of some oftheir recent releases to understand howthe design org operates. And Cam is alot of fun to listen to, so let's diveright in. The amount of change that hashappened in 2 years, not just at CashApp, but like the industry at whole isabsolutely nuts. If you just think aboutit, right? It's It's we've had an entireset of tooling we're using changing. Theentire speed that someone can produce asimilar output has changed. The entirelike

00:01:15organizational structure has beenput into challenge. So I think on a goodday without all of the like crazyindustry stuff, I think it would havebeen a crazy 2 years, but then when youthrow all of like the AI change on topof it, it's been an absolute blowout,but to me what I love is driving changeand I think that's why I feel like II've been I'm reflecting back on 2 yearsbeing like I'm pretty proud of wherewe've got to. We've really got an insaneteam. We are working in a way that feelsvery modern. We're small and nimble andable to kind of pivot with the changesthat happen every single week. Andultimately we're just producing reallygood work.>> I mean I think you have every right tobe proud. Even just digging through someof the recent You had a pretty bigrelease just a few months ago. It was abig deal And across the board it wasreally high quality. So part of my goalof this conversation is to dig into someof these modern ways of working. And Iwant to start with a phrase that youused last time we talked where youtalked about like almost your mandate isthis high quality, high velocity. Sowhat about this big release that youjust shipped at the end of 2025 do youthink shines a light on how you wantthis design org to operate? I thinkhistorically in product developmentthere used to be this insane trade-offthat you can either have it of highquality

00:02:30and it has to be slow or you canhave it fast but then it's bad. And Ithink the change that I've felt the mostover the last, you know, six months to ayear and even since like November it'sfeels like another exponential changeagain is those trade-offs no longerexist and you can move fast and you cando it with high quality and to me thatis just exceptional. It doesn't meanit's easy to do. I think the the way youachieve both of those thingssimultaneously is you have to run verylean teams. You have to be incrediblyclear on the outcomes which those teamsare trying to achieve and then you haveto make sure they're using these toolsin a way that allows them to 10x outputand you know, the amount they producebecause I think the quality piecethere's a misconception that it comesfrom a designer sitting in some cave forthree months and pontificating about thefuture of software. It literallydoesn't. It comes from reps and the thespeed which you can be wrong and thespeed that you can go again andexperiment and experiment experiment.And I think that's what we've seenchange is the amount designers canproduce has exponentially increased andthe amount of like bureaucracy andlayers you need to run an organizationhas

00:03:45changed a lot as well. So you kindof package that together and and allowsyou to produce significantly more atreally high quality at a really highspeed and it's just like a productdevelopment dream, at least as far asI'm concerned.Real quick message and then we can jumpback into it. An even smarter version ofLovable just released.>> [music]>> It is 71% better at solving complextasks, which means it can do more workmore autonomously. There's moreintelligent planning,>> [music]>> it's prompt queuing, so you can stackrequests while Lovable works. And myfavorite part, there's automatedtesting, which means Lovable now testsyour apps like a real user. Opens itsown browser, navigates flows,investigates edge cases, and catchesbugs for you. And the best part is whenit finds a problem, it fixes it right onthe [music] spot. I genuinely believeLovable is the easiest way to buildsoftware today, so head todive.club/lovableto try the new release.You know what I'm excited about? TheGranola MCP. It allows you to connectyour AI tools [music] directly to yourGranola meeting notes. And as somebodywho's been vibe coding a lot of toolsrecently, this release is a pretty bigdeal because my meeting notes are someof the most valuable context [music]that

00:05:01I have. And now I can find specifictopics, pull out action items, and getany question answered based on mymeeting history. This is all availabletoday and I'm already building with itlike crazy. So, if you want to join me,head to dive.club/granolamcp. That'sgranola-mcp.Now, on to the episode. Let's dig intosome of the organizational changebecause you almost kind of drew thisline at like 6 months ago and then youknow, like November, December maybe. Ivery much so see those as these twoinflection points as well. But then likehow does that trickle to a design org?Like you as a leader trying to makesense of how do we want to operate giventhe rate of change of all these toolsand what is possible and it just feelslike a lot of the old rules don't applyanymore. So, what do you even do withthat in your position?>> Yeah, yeah, yeah, yeah. It's like acomplex question, I think, that there'snot one answer to. The way my brain kindof initially goes on this previously iswhat are the old rules, right? And ifyou think about the old rules, it usedto be that there was this productdevelopment pod, and it was an embeddeddesigner, and it was an embeddedengineer, and product manager, and thenthe pizza team, essentially, right? Andthen you'd have a lot of these pizzateams, and then because there's therewere a lot of pizza

00:06:16teams, you'd need alot of management layers. Then you'dhave a bunch of managers, and then thosemanagers would also have managers, andthen you'd have a bunch of structure.And before you knew it, you had thisweb of these giant orgs with like sixmanagement layers,lots of small teams, and lots of peopledoing like micro-optimization in there.And I think what's changed from astructural standpoint is because theamount people can produce is, yeah,probably like 20x, 30x, maybe even 100xsometimes, then you don't have to havethis old model. So, what you can do, andwhat we were able to do, is flatten theentire organization. So, we have thisrule in design which we have core plusthree, which essentially means we'reonly three management layers away fromJack, which is actually quite crazy whenyou think about a company of our size.When we first decided to flatten, it wasthe thing that we were most nervousabout, but actually since we did it,it's been the thing that I've receivedthe most positive feedback on. And thereason is you flatten it and basicallyit just goes Jack, Brooke, Cam, and thena layer of what's like that's it. Andwhat it allows us to do is not kind oflike, you know, there's no hiding invarious management structures, there'sno game of telephone. It really justprioritizes the people who are building

00:07:31the software and the product week inweek out, and then they get to skip abunch of layers and just report up. So,I think that was probably one of themost intentional things that we've done.And if you think about that at like whatthat actually allows you to do when youwhen you kind of change theorganizational structure and justflatten it, it just allows you to bemuch more nimble. So, when somethinghappens in say November and we're like,"Oh my god, the game's changed again."We are not working through six layers ofmanagement and having to like keep thosefive people aligned. It's a very smalltight-knit group of leads where I justhave one standing meeting on a Monday tokeep them in sync, and that's it. Noone-on-ones, no nothing, just one onemeeting a week, and then the rest of ourtime is just spent building, and that'sreally what's unlocking some of thesethings. There's there's tons and tons ofstuff in there, but I think if I was toreflect what's been the single biggestthing we've done that has allowed us tokeep with the pace of change, it's beenreally challenging the traditionalorganizational like product developmentstructure that I think people used todeliver software at scale over the lastlike 10 years. Can you push on that alittle bit and talk about how thatimpacts the practice of design or anyprocesses, rituals? Like what does existstill in that more flatter org? And werethere specific elements of how you all

00:08:46did design that you actually removedgiven those changes? It's interesting aswell to look at like the before and theafter, right? Cuz that's actually whereit gets kind of interesting. So, we havean uncomfortable lack of process. So,often some people join and more recentlythey've been like, "Woah, this is kindof like a shock." And they And it's alldocumented, but all of our process inCash Product Design, I can I canactually picture it right now. It's It'sabout five lines of stuff. Like itliterally just like sentences, just likethis is like the thing you have to goto. And And that to me talks to justlike the cutting we've been able to doon that. And the reason I think that'sreally really important is processexisted, from my perspective, to provideconsistency in output when designstarted to scale and becomeprofessionalized. So, you know, backwhen I first started design, it wasn't Iwould I would say it wasn't reallyprofessional. We just used to kind ofwing it.Uh we we just would like kind of run onvibes mostly and like what we felt feltgood. I'm sure it was probably the samewith you. And then as, you know, youneeded design orgs to be 300, 400people, 1,000 people, you had to put inprocess and structure in order tosupport that many people. The realquestion which is has been kind of beenput into motion over the last year, 2years has been

00:10:02of that process, what isserving you and what isn't serving you.So, we've just basically just likesystematically gone through and deletedan uncomfortable amount of stuff. Like,for example, everyone is obsessed withdesign crits, right? And says, "Ah, soessential to our process." If youactually do like a ride-along at a of adesign crit at a lot of largeorganizations, it's not really a strongcrit in like the traditional sense.People are just telling everyone, "Ah,your work's lovely. Ah, your work's sogood. YouMaybe push it over here." Or they likeput another post-it like a few post-itnotes on there. And then most times likethe designer leaves that crit andprobably ignores like 90% of thecomments anyways, right? Like youprobably expect that.And then it's like, "Well, what was thepoint of that?" You spend an hour, youbrought everyone together, so why don'twe just try deleting it? And so youdelete it and then you see what happens.And and then I think we kind of has justsystematically gone through all of the,you know, kind of professional designprocesses that we've held clear and thenjust found a way to just like run very,very lean. So, if you're a kind of IC atCash App, the week in, week out, it'sit's pretty simple. You basically justget together and plan with your team ona Monday. And then if you get stuck,

00:11:17there's standing time on Wednesdays tounblock, but you know, it's optional.You don't have to unless you're stuck.And then on Fridays you just demo whatyou built. And that's like shared. So,it's really it's very bare-bones, but Ithink it actually starts to get back tome to the pureness of productdevelopment where it didn't need to beas so complicated and we didn't need tohave these like checks and balances tosupport all of these hundreds andhundreds and thousands of connectivetissue points. It's just It's justgetting back to building again. And tome that is just like the most energizingthing and I and I honestly think it'swhat sped us up so much is justevaluating all of that stuff and seeingwhat serves us and what doesn't serveus. I love the two anchor points beingplan and demo kind of at the bookends ofthe week, too, because in my experience,if you do have that crit, like theformal crit, where you're actually goingto get like {quote} approval or like getunblocked, per se, a lot of times, youknow, I'm guilty of just waiting. Like II'll just wait.I'm just going to wait 3 days until Ican have that meeting and then I'll justask those two questions that I need toget answers to.And it's like that just doesn't cut itanymore given like what you were talkingabout earlier, this this speed of repsthat you can do as a designer that justdoesn't translate.>> For me, I think the biggest blockersacross all of the tech industry

00:12:32in thenext 2 years will not be the speed ofbuilding. It's going to be theoperational side and being able to movesomething from like we have built thisthing, how does it move through theoperational cogs of product developmentin order to like get it live tocustomers? So my view is like how do weset ourselves up for the new world? Youhave to make sure that your organizationis capable at running at the same speedas the AI tools. And these AI tools movelightning fast.>> They're fast.So so like to me that's like an entire ahabit we're trying to change within ourorg around is like the pace and theurgency that we bring into justeverything. And then that means thatthey are keeping pace with this toolingand I think to me that puts an org in amuch better state for the future. Let'stalk about the Friday demos piece for asecond. Like what does a great Fridaydemo look like compared to maybe aslightly more mediocre one? The linesbetween disciplines are blurring, right?Cuz designers now coding stuff andengineers are still coding stuff aswell. And even product managers arecoding stuff. So, to me, a good demo, Ifeel happywhen I've finished Fridays and I'vetended to pop around a lot of demos,when I just feel there's been liketechnological breakthroughs. I can'tlike say too much, but a lot

00:13:47of thetimes over the last few weeks, there'sI've been going to demos and I've beenseeing what's being built and it reallydoes feel like invention, I guess, andthat we it's not just informationsharing, like, oh, here's what I builtthis week. That was in spec and we'vefulfilled the answer in the spec. It tome feels like a, you know, we had thischallenge and this outcome which we weretrying to achieve as a group and wewe're on like the fourth prototype of itand this one almost works.I guess is maybe the best definition.And it's scrappy, it's raw, but you cansee like a glimmer of a technologicalbreakthrough. So, for example, Moneybotwas something we launched in our fullrelease, right? I remember seeing thefirst demo actually on web of Moneybotwhere we basically took a customer'sdata and like all sorts of our data,we're able to like feed it into thisthing and have a response back. And itwas probably the design was not good.The execution was so slow, it took sofar to spin it back, but it was thefirst moment where you could feel thepotential and you were like, oh, wow,we're like having breakthroughs here. Ina good week-on-week basis from demos,those breakthroughs tend to likecompound and then that energy just likefilters into the team

00:15:03and then I've atleast seen people want to keep likeleveling up on those like breakthroughswhich are happening at demos. So,there's there's no like formula per seother than just show us what you builtthis week. If you built somethingincredibly complex that's really hardand you've broken through, great. Ifyou've just built something that's rawor if you just doing animations for theweek and final mile polish, that'sabsolutely fine. It's just show us whatyou made this week. I think money botsare a pretty interesting thing to lookat because so much of what makes itspecial existsoutside of the pixels, you know? Like alot of the design even is outside of thepixels. So maybe we could even use thatas an example to talk about how thevalue prop of design has shifted at CashApp, both maybe due to the the type ofproduct that you're working on, like amoney bot, but also it sounds likepeople are experimenting more with thesetools. You talked about the value oftechnological breakthroughs, more peopleare coding. Like what has that shiftlooked like in practice at Cash App?Almost all of our products now are nowlike shipping PRs. And I found it kindof funny. I can pull the the data offthe my top of my head is like over 90%.It's like kind of crazy. It's a bigdeal. Yeah, so it's a big deal. Butwhat's funny is designers keepgravitating towards the most designerystuff. And I founda lot of designers

00:16:18are fixing thesesmall refinements in the product thathave bugged them for years. And it'sjust been like a funny course of action.It's like you get keys to the kingdomand you can ship these insane things.And then designers are like, "Oh, thispixelation on like this screen was likeit was really awful." Likethe amount of keyline alignment I'veseen.Like we've got we used to have themissues in our app where those qualityand paid some pages would be likeand things just weren't quite perfectpage-to-page. And there's two designersI'm thinking of in the top of my headwho are just like smashing through PRs.And Lauren has this great group like thepixel janitors. And they are like thepixel janitors who are just like going[laughter] going around cleaning upafter our developers who like didn'tmake the app completely pixel perfect.So I know that's a tangent off thequestion, but I think that's that's justan anecdote which I'm finding so funny.But I think over time they'll startbeing pixel janitors and designersshipping code. And then confidence willjust grow from there and grow and grow.And I I do see a world in the not toodistant future where very complexfeatures are being, you know, shippedvia just a builder and you can'tdistinguish whether that builder is anengineer, a designer, or someone else ina discipline.Uh they're just able to visualize

00:17:33andinvent something and just ship thatthrough these tools. So that that'swhere I can see it going. I just thinkit's going to slowly be like aprogression and then we'll wake up oneday and it will be like, "Wait, there'sno more rules. Where it's just who canship?">> Good stuff. And I I can really see thattrajectory already happening. I'mfeeling that a little bit even for myown practice. Like I've made a couplePR's in the last few days and I'm like,I just honestly step back and I'm like,"I can't believe it. I cannot believethat I did that." You know, it's so pastthe line of the like P3 polish ticket.That being said, for you to even getclose to that at an org that's so muchbigger, you know, and you'reif you're even close to this 90% number,that's a pretty incredible feat. So hasthere been any like top-down investmentor anything that you're doing to helpdesigners get more comfortable with acode? Is it just happening organically?Like how have you been able to see suchan organizational transformation oversuch a short period of time? I think[clears throat] we've been far ahead inthe tooling aspect that enablesdesigners to do this. So we've had agroup of people who essentially look atthe AI enablement side of it and there'san entire program that's dedicated tocode fluency and that's helpingdesigners from zero where they don'thave a GitHub account all the way tolike shipping API into product. Thefirst stage

00:18:49starts in like a sandbox PRso you can kind of mess about and thenum once people have kind of gotcomfortable shipping inside of asandbox, we move into like the actualproduct and then there we found someengineering pairing is like reallyhelpful just to help designershonestly just like navigate it. Like Idon't think it's it's necessarilybuilding the code which is the hard partanymore. It's it's more so which buttonsdo I press and the world doesn't end,essentially.>> [laughter]>> So true. So so so and you're just likethere and you're like, "Okay, I'm notlike a technical but you know, I'm nottechnical in the sense of like adevelopment." And you like read some ofthese things and just even the filenames, you're like, "What is this?" Andso>> Every button in GitHub is scary, too.Like even the the squash and merge. LikeI looked at that and I'm like, "It'sgreen." Green normally means like it'sokay to press on, but I'm like, I got toGoogle this." And I'm like, "I'm sureI'm like, do I hit the squash and mergebutton?" Like it's very clearly the onlybutton on the entire page to hit, but Istill I still couldn't get myself to hitit. Yeah, that's that's uh that soundsabout right. I think by the end of Q1we'll have we'll be at 100%. Like we'vegot a few people who are obviously outof office and stuff like that, but yeah,we'll we'll have every single designership have have shipped production PRs bythe end of the quarter, I think. World'schanging. It's one part of it, though.Like I think, you know, there's stillthe building

00:20:04part, but there's stillthese other jobs that happen in this newworld that to me are just like just asessential and even more important inthis new world as well. You want to go alittle bit deeper there? We basicallyhave a DRI concept and and that standsfor like directly responsibleindividuals. And the DRI's areresponsible for leading a large group ofICs to achieve an outcome. And what'sreally interesting from my perspectiveon that, right, if you actually thinkabout it, is there's so much stuff youcould do. The real challenge thenbecomes if I if I've got this infiniteset of options, like what is thestrategy and how do we coalesce a largegroup of builders to deliver on thatstrategy fast so that we win? Likethat's an art form in itself that Ithink is just as critical. Cuzotherwise, what you'll end up with isyou'll end up just so much shipping, itwon't click together. Mhm. It will be,you know, one part of the org's goingover here, another part of the org'sgoing over here. So, these tools areamazing at increasing the amount ofoutput, but output without that tasteand that ability to be like, this iswhere we're going strategically as acompany and these are the people who aregoing to like help drive us week

00:21:19in weekout towards that direction. And that tome is just as critical as the people whoare, you know, shipping the code andbuilding it day to day. Um and I thinkdesign also has an opportunity toreally, from my perspective, like stepinto that role becausedesign can visualize what the futurecould look like. And a lot of otherskill sets can't do that, right? Likepeople have to write documents orsomething like that, but, you know, ifif we're trying to go after, say, thenext version of Moneyball and talk aboutit in the future, a designer canactually prototype something, show it toeveryone, and be like, this is thedirection we can go, and then everyone'slike, yes, let's follow that, right? Andthat allows this group of builders toessentially like know where the strikepoint is. Um so, maybe maybe a good wayof articulating it is I think as theoutput increases, the the value ofclarity and vision just becomes more andmore important because otherwise youwill end up in this jack-of-all-trades,master-of-none software, I think. Maybewe could even tie a bow on everythingthat we're talking about here becauseI'm sure some people listening areexcited by all of the change, but also,you know, people are trying to figureout almost like career strategy, youknow, like what's the North Star that Iwant to even point myself at

00:22:34in terms ofwhat I want to bring to the table 1 2 34 years from now to continue practicingas a professional designer. So, when youthink about maybe even like thearchetypes of designers that are havingreal success in your org, where do youkind of draw the lines? Like where cansomebody point at or the decision matrixof what type of designer do I want to bewhere I could thrive at an org like CashApp? When you're in these periods ofrapid change, the most important thingis being valuable and then being able toreinvent yourself again and again andagain at the pace of change. So, if Iwas to give any advice on like long-termcareer longevity, is I'd say there is nofighting this direction of travel,right? It is fundamentally changing theentire product development process. So,retooling is not a luxury, it's like amust-do. And I I think it's going to beif you're not AI fluent and I think youwill struggle to get a job, to behonest, in the in the not-too-distantfuture. You might even struggle now. Iwas about to say we might be therealready. I think I think so. It's hardto say, but I think it's just like thetruth. And then I think as far as likethe evolving shape of it, I I honestlydon't know, but there's there's threearchetypes which we're working towardsand I think at the highest

00:23:50level, it's aworld where the lines between roles area lot more fluid. And we basically uhtalk internally at Block and I can'ttake credit for this, but there'sbasically a DRI, he's the person who'sdriving the work. There's ICs who arethe craft makers, taste makers, drivingthe actual execution towards that goal.And then there's player coaches whichare like the leadership layer of theorganization. I can like go into eachone of those, I guess, from I think aDRI is is a really interesting thing tolean into, particularly as a designer,because uh your strength as a DRI isessentially is your ability to take aloose strategic nugget as a business,right? So, for example, at the momentI'm very focused on this idea calledNeighborhoods, which is how we connectboth sides of the counter between Squareand Cash App. And if you think aboutthat, that's like fascinating problem tosolve. Why when you walk into everysingle Square shop cuz you don't paywith pay with Cash App? There's noreason, right? And it's like avery technically interesting challengeto solve, but also very customer-centricexperience challenge to solve. That'slike a an important role, which I thinkshapes the future of design. It's likepeople who can take Maybe a good way toframe it is like creativeproblem-solving

00:25:05and start to think aboutwhat are the biggest problems that thisbusiness faces and how can I usebuilding and product development anddesign thinking to help people visualizeand follow me on that change? Likethat's a role which I think will stillbe really important. And then on the ICside, the ICs that are thriving at themoment are what I would just call likejust builders. They are people who biastowards action. They are very outcomefocused and solution focused versuslinear process focused. They're justlike, "Okay, cool. We're going toconnect both sides of the counter withthrough Square and Cash App. Let's juststart building some prototypes of how wecould potentially do that, get that intocustomers' hands. They're not scared ofbeing wrong. I think that's like theprobably the most important trait thatI'm seeing is like ICs who are willingto be like, "I back this as the firstdirection." Is is is is actually aundervalued skill and I think those ICstend to be like really really thrivingat the moment. Um and then in theplayer-coach space, there's still a adeep need for leaders in design. But wedid this before the AI push, but we'vewe don't believe in like professionalmanagers in the sense that other largetech companies might have.The idea

00:26:20to me that you have a managerwho is not responsible for the output oftheir team is just like one of thedumbest things in the world and justdoesn't compute with me. Um so ourmanagers are our leads, we call them,are player coaches. They are responsiblefor driving outcomes and positiveoutcomes in the team and all of thepixels which they're pushing and theirteam is pushing, they are responsiblefor. So those are the three archetypeswhich we have and I think across thosearchetypes you're almost seeing likedifferent skills prevail and you know, Iwould summarize it as like the DRIs arelike the people who are able to kind ofdo like creative leadership essentially.Um the ICs are just the builders whojust produce and create amazing highcraft outputs. And then the playercoaches are essentially the people whocan kind of lead the ICs towardsachieving great outcomes. And that'sgenerally what I've seen, but maybe theinverse of that would be I don't thinkthe kind of middle professionalmanagement layer who doesn't actuallyproduce stuff will exist. I I don'tthink it exists anymore perhaps in theway it did three years ago. I rememberinterviewing at a big company andthey're like, "Do you want to be an ICor a manager?" And I was like, "Can I beboth?" And they're like, "No, no, no."And I was like, And then people wouldhave invested like five years of theircareer in just being a pure play managerand then they're

00:27:35then they're kind of now.>> it's tough. It's tough. I genuinely feelfor those people. And yeah, I reallylike DRI a lot becauseI think it's been easy to evaluate whereyou want to grow as a designer on kindof the you know, engineering producttriad a little bit. It's like, "Oh, do Iwant to go down the code path

00:27:57felt like a departure from design insome ways, but it's so clear that likethere's this need on like the stick thestrategy. You said creative problemsolving. I love that, you know, it'slike AI is accelerating everything. It'slike, "Great. The bottleneck in someways is ideas."You know, like you got to you got tocome up with things and direct thingsand I totally believe that designersmight be the best positioned person tothrive in that role. Yeah, I I feelsimilar. Being the ideas guy always usedto be like a joke, right? Yeah.And now like actually it might bevalued.>> It was such an insult like 18 months agoon Twitter and now it's like, "Wow, weneed more ideas guys. Hey, we're hiringideas guys." Yeah, [laughter] yeah,maybe maybe it's different there. It'slike the most successful DRIs like I'mthinking of Ryan and Owen therethey're super senior people in thecompany. They're they're DRIs as welland that obviously Brian was like theold CEO of Cash App. He's like theperfect definition of a tier one becausehe could justhe could just make stuff happen andthink strategically, but it's a reallyfascinating thing because you do needmore of those people at different layersand you have to build a bench of highlycapable leaders who can essentially, youknow, lead the the robots plus thehumans to deliver these outcomes and Idon't think it's as simple as peoplerealize

00:29:12and I've definitely seen eventhrough friends or even, you know, frompersonal experience at Cash App where ifyou have just like a bunch of peoplebuilding stuff and making stuff, butit's not being shaped into like acoherent direction and strategy withtaste and curation, it kind of justfeels a bit rudderless and you're likeproducing stuff, but it's not reallydriving the impact and that to me isperhaps one bit which the industry atlarge is maybe not talking about becauseyou can make stuff and build stuff allday, but if customers don't want it,it's kind of pointless, right?There's one question that I can't stopasking myself. What if companies appliedto talk to you rather than the other wayaround? And that question is thefoundation for the all new Dive TalentNetwork [music]and it's working. Like right now, I'mhelping many of the most excitingstartups that I know to hire thedesigners and builders who listen tothis show. So if you're curious whatmight be out there and maybe want to geton my list or maybe you're even lookingfor your next design hire, head todive.club/talentto join today.Okay, so we're talking a lot aboutarchetypes and everything that'schanging in the world. [music] Myquestion then is how's this influencingthe way that you're thinking about

00:30:27hiring and [music] maybe even like thesignals that you're prioritizing andevaluating people and trying to figureout who's the best fit to bring in tothe team. So I think the thing that'suniversal and is and is never everchanged is someone a good designer. Andthat might sound stupid, right? When Isay that out loud, but most people faila portfolio phase or an interview phasebecause theydon't have what I perceive as one of themost important things in design, whichis essentially craft. I made that 90%up, but I actually think it will beprobably closer to like 95%. Everysingle rejection reason, I think thenumber one up there by an exponentialamount is like craft. I think the otherstuff that surrounds craft is mucheasier to teach.But someone's like innate eye and tasteis actually the most valuable thing thatI think I've time and time again had.Like there's a lot of people who I'mthinking of who you could just tell theyhad an eye for it, and they hadn'tnecessarily had the opportunity. Andthen you give them the opportunity, andthen the eye prevails. And to me, likethe eye implies that it's just this likevisual only thing, and it's not. Youknow when you look at a product and itjust feels right?And they've balanced

00:31:42it, and it justfeels like incredibly obvious. That's areally hard value to place on something,but I think it's actually probably thesingle most important skill as like adesigner. And I think as the number aslike the amount of output you canproduce comes up, we're going to see aton of slop, and then we will see asmaller and smaller amount of designersand people who can really just likeselect with such intention and focusthat they know what good looks like. Andso to me, that's been like the universaltrait that hasn't changed. Like craft,taste, whatever you want to call it. Andthere's a misconception that it's justlike the visual side. It's not just thevisual side. It's like it's the combo ofit all and it just feeling right. Likethat's that's really, really important.And then I think the other stuff thatwe've seen change more on the hiringside is just general AI fluency andstuff like that is just kind of a givennow. I I think it's unlikely that youget through the interview process if youweren't building some stuff in AI andlike had some other projects. There'ssome people for example who work atcompanies who are as AI fluent but haveinsane craft levels. They tend to bebeing like, "Oh, on the weekends I builtthis amazing tool." And you can kind ofconnect two and two and you're like,"This is enough." Um so, I don't know ifthat answered the question but I thinkthe most important thing to say there iscraft always shines through

00:32:58and now morethan ever even if you look on Twitterand you see the people who are likegrowing their followings exponentiallyas like an IC is craft. [snorts]Like they're building amazingprototypes, they're building amazinginteractions and I just don't thinkthat's disappearing anytime soon. So,that's what I keep looking out for andthat's what a lot of people at Cash Appand and I think that's why the fit andfinish of the app feels quite nice cuzwe have a lot of people who care reallydeeply about that stuff. I want to drillinto the AI fluency piece a little bitand I want to speak to a very specificlistener whohears you, maybe they've actually beenkind of punting all the AI stuff cuzit's annoying and they don't have timefor it and you just convinced them.You're like, "All right, shoot. Like I Iactually really have to invest in this."But it's unclear where is the threshold?Like what line are you trying to seedesigners get over where you can say,"Yep, they have what it takes andthey've experimented enough or they'vebuilt enough." Say If you're an IC andyou're a builder type, I would guess andI may be wrong that if you're askingyourself that question, you're probablynot a builder. Because anyone I know whois thriving in this like builder firstIC world, they are so emotionallyenthralled by this change that ishappening because design was always

00:34:13gated behind technical expertise and itwas always like you needed someone elseto realize your vision. The a lot ofpeople I know who are interviewing andor work at Cash and Block andeverywhere, they are like shipping funthings on the side just to experimentand like have fun with the technology.Um and that is by the for me from an ICperspective, like that is a builder. Andthey bias towards action, they lovemaking. If they have half an hour free,they're going to tinker on somethingthere. I guess that's like a way toprobably like challenge the question alittle bit that if you're askingyourself that, I think maybe maybe thebetter question is can you compete withthese people who are high craft, hightaste, and building at incredibly highvelocity and like figure sprint to bind?And honestly, I would say if you can't,like don't get in the game because it'sprobably not worth it. You're not goingto have a gig. It's a good answer,honestly. I I respect the pushbackbecause building is pure love of thegame at this point. It's like like yousaid, like we've as an industry, we'velike almost like had this coiling ofman, it'd be nice to build my ideas andthen all of a sudden there's like boom,and now you can. And it's just like,okay, cool. This one, this one, thisone, this one. That's tough to competewith. If you if it doesn't comenaturally and you're not excited aboutit, it's tough to compete with. So thenthen what?There's other things, right?

00:35:28So likeyou know, in in a leadership role and insome of the other archetypes whichyou're looking at, then the skill set ismore so like how do I shape anorganization and shape strategicdirection for these ICs who areproducing the same amount of stuff? Likethat's the skill set in itself. There'sno like course on that, I don't think.And if there is, you know, someone willprobably make a lot of money. I thinkthat's a skill set that's incrediblyvaluable in this world. It's likecreative leadership or you know, I don'tknow what the answer is in exactly howto define that, butthat's maybe a space which people Ithink could go into if in this world,but it's going to be harder. Like that'sthe honest truth. Design jobs I thinkwere plentiful and everyone neededdesign. And I think what you're going tosee is there'll be fewer gigs becausepeople can achieve more with less. Andthat to mejust means the standard gets higher andwhat people have to produce. So I justsee the quality of people getting betterand better. So I think it's also reallyimportant to like caveat that in thistime that I think the design industry atlarge got really guilty of overvaluingpeople's resumes on a logo. And Itransparently like don't give aabout where

00:36:43someone worked. Uh he'llprobably kill me for saying this, butlike one of our best designers, handsdown, and I think he'll come on to belike one of the best ICs in the company.Uh his job before was like workdesigning stuff for Yo! Sushi. No shadeat Yo! Sushi. It's cool, but it's notlike the the Airbnb or like the Meta ofthe world. Um and I think it just comesback to raw talent shines through. Andraw craft and raw skill shine through.So, for the ICs of tomorrow, I thinkyou'll just see them bubbling up. And wehad this like we had these builderfellows join recently who are like freshlike no college fresh into working withus. And the amount of like the skillswhich they have, uh they're just likeSwiss Army knives. It's terrifying. Andthey can literally do it all. Yeah. Umso, yeah. I I know that's like a bit ofa long-winded thing, but I do think it'simportant for us as like design leadersin this new world to not be overlyattached to the resume logos and all ofthat kind of As actually withit and just look at raw skills ofsomeone building and transparently frommy side, and I know I speak for all ofBlock that we don't care where someoneworks, we don't care where someonelives. It's just like, do you have theappetite to work in this high-velocity,you know, high-craft environment, and doyou have good taste and could pull itoff? So, hopefully that changes,

00:37:58butagain, I felt that was an important PSAto say. No, I think it's great. I'm gladyou said it because there's a lot ofreasons to be intimidated about thefuture, but that is the reason to beoptimistic. Like this is the greatleveling of the playing field. Literallyjust today, we released an episode withthis guy who just landed a really coolfounding designer role through thetalent network. Andhis resume sucked.>> [laughter]>> Okay. Yeah. Yeah. Yeah, he would hewouldn't even feel bad about me sayingit. Like he he didn't like the companyhe was at. It was very low craft. And hejust went out and made a ballerportfolio and a really cool side projectand sweat a bunch of details on hisportfolio site and it was more thanenough for me to like, "Okay, this guy'sreally good. What the heck? This guy's agem." And he will fly past people who>> Yeah. you know, dare I say maybe havespent the last five years at Meta on atiny little slice of the product becausehe is like this generalist that AI isaccelerating in every single direction.That archetype, so so exciting. And forthe first time in in a few yearsprobably, like this is their moment.Like if you are that person, this isyour time right now.>> I've recently joined Twitter again and Ilike DM quite a lot of people where Ijust that work pops out. I'm like, "Thatwork is sick." And I and I don't look attheir LinkedIn. I don't I just likelet's chat. And people

00:39:13will get jobs offthe back of that. And it's not sayingyou like you have to post all your stuffall the time, but it just builds and itand it just I don't know. I just thinkyou just see craft cutting through arate that it didn't before. Andpreviously perhaps, you know, you wouldgo to a large tech company and therewould be like 10 rounds of interviewsand everyone would be like, "Tell usabout this. Tell us about this." And itwaseasier to get into the CIA than somelarge tech company interviews. Whereasnow it's just like, "Show us what youbuilt." And I I absolutely love whatfeels to me like the smashing down ofthe last 10 years where the tech designbecame bureaucratic,overly professionalized,and now it feels like we're getting backto basics and that to me is just soenergizing. And that's probably why I'mso hyped at the moment at work. I wantto return back to something that yousaid earlier. And you were talking aboutthe connection between Cash and Square.Yeah, and neighborhoods. Yeah, and andlike there was a tweet that I hadcircled that you put out. I don'tremember a couple weeks ago where youjust talked about how something you'rethinking a lot about is that, you know,creating a shared DNA, like visual DNAeven between Square and Cash. That's nota small project or initiative to leadgiven

00:40:29the scale that we're operating at.So, can you just shine a light on someof the things that you're thinkingthrough on that front? It's not justlike changing design language forchanging changing design language forsake. That's like the best way to to tophrase it. If you think about thatproblem which I talked about earlier oflike connecting both sides of thecounter, there is a customer experienceand like design language part to it thatwhat works about the Apple devices whenyou go from like an iPhone to an iPad toa TV is there's this feeling ofsimilarity even though they're differentOS's and core experiences that makethese handoffs feel like very seamless.A while ago, because Cash App and Squarewere pretty separate until wefunctionalized the company,there was no incentive to think abouthow that connected, right? So, they wereby and large like separate things. So,if you had to design like this verysmooth handoff at that time, it wouldhave felt like you were, you know,handing off between Toast and Venmo,right? Because it's two separatecompanies. So, actually like Square andCash App are a single company and we'regoing to connect them and it's going tobe one of the coolest things ever,but we need to make sure from a customerstandpoint that the experience feelsseamless. The obvious answer there is,"Oh, let's just make them both the same.Let's just make Cash App and

00:41:44Square likehave the same design languages, have thesame systems." But then if you reallyinterrogate that, it's like, "Oh, wait.Cash App is like one of the most crazyculturally relevant brands that appealsto like a very young generation. We'vegot 25% of US teens." And then Square islike a hardcore working B2B softwarewhere people are in the app for like 8hours a day. Um so, if we start like,you know, dropping crazy illustrationsand tons of white space everywhere, wemight, you know, people might getannoyed.>> [laughter]>> So, what we started talking about as agroup is that well, how do you connectthem? And I think this is where it comesdown to that deeper layer of likestrategic drivers. And this is somethingthat was involved in and deeplypassionate about is actually design runsdeeper than that and you can start tothink about what we call shared DNA. Andthis idea that it's siblings, not twins.And if you think about that as theanalogy, what we're saying is there isshared foundations that make it feellike it's a block designed product,whether that's type, some shared likebase tokens, approach to the grid, andthen there are these uniquepersonalities that get put on top of itthat allow each of the brands to shine,but also make that handover moment notfeel like you're jumping between twodifferent companies. So, that's I guesswhy it's

00:42:59it is interesting because itreally is like design as a strategicasset because we're using design tosolve a customer problem and to solve abusiness problem, which is how do youconnect both sides of the counter. Oneof the personality glimpses that Ireally liked from the latest release wasthese personalized payment pages. Canyou just give us the backstory there?Like how does a project like that comeup, get greenlit, be brought to life?Like what does it take to pull somethinglike that off because it definitelyexists so far outside of the traditionalbox of responsibilities that a lot ofdesigners, especially people working onB2B, get to even sniff. That's like apersonal one. I I still think we cantake it even further. Again, it justgoes back to that like creativeproblem-solving again, right? Mostpayments, essentially like moving moneybetween you and I, it's become acommodity. So, the prompt there is howdo you start to make the experience ofmoving money between you and I feel lesscommoditized? And if if you and I werejust to now to like ideate on that,you'd be you'd probably say that oh,well, what if you could like send aspecial message? And then you're like,okay, cool. So, what we did is weactually looked at the messages thatpeople were sending in their paymentnotes. We pulled a list and aggregatedit again like using AI, we're able tolook at you know, millions and millionsof payment notes and find out like whypeople are moving money. And you seethere's a lot of

00:44:14things that are kind offunctional, right? So like rent, youknow, no one's celebrating rent.But you also see there was a lot of veryemotional things. Like for example,graduation, birthdays, dinners for aspecial reason, right? And then you kindof pull that thread and you're like, whyshouldn't that experience be more thanjust this like sad utilitarian thing?And it shouldn't. So we were like, let'sdesign a bunch of custom assets thatmirror all of these moments that peopleare sending money. And that's where westarted to like see if it worked and seeif customers are loving it. Customers dolove it. They're like big advocates forit and I think we will continue to pushthis idea that it's completelypersonalized and moving money doesn'tneed to be this like commodity for therest of the over the rest of the year. Alot of the things that you're talkingabout related to maybe finding theshared DNA, you know, people translatemore into this like design systemsbucket. I know Lauren is leading thatdoing a great job there. And yet much ofwhat comes out of Cash specifically islike frankly bizarre, you know, it'sjust very, very different. Can you talka little bit about like that tension?Like how do both of those things operateat a high level where you have this youknow, the systems required for craft atscale while also trying to

00:45:29be deeplycreative in the core brand and what thatexpression looks like. It's like one ofthe most existential challenges that Ithink every tech company should bethinking about deeply right now. I thinkit's better to be on the side ofexpressive and unique to customers sothat they have an emotional attachmentto your product versus like you know,consistent andessentially 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'tdesign at the moment, but it's outthere, is like Bump. I don't know ifyou've used Bump. It's like map app. AndI like met the designer and he's likehe's like, "Yeah, we just we just YOLOanything." Like it's just like how weirdhow weird can we make it?>> Friday's episode is with Julian Martin.Yeah, yeah. Well,mad respect. I think that that's a goodexample of like I just think you haveto. And we're definitely forcingourselves to get out of our comfortzones. I guess it's maybe the flat wayto describe it because the traditionalproject was oh, consistency isruthlessly adhering to this very strictdesign system was the only way to adhereconsistency, right? That was like thetruth for a while. And I don't thinkthat is necessarily true. Like a designsystems have to be able to

00:46:45flex andallow for more expression. And then Ithink if I put the new age layer on it,I believe one of the primary ways whichyou will create lock-in in in the newworld is creating apps that feelcompletely one-of-one. So, what I talk alot about Cash App isI want it in 6 months, a year, I wanteveryone who's sitting at a dinner tableto open their Cash Apps and put them onthe table and every single one looksdifferent. It's a complete expression oftheir personal identity. And if youthink about it, like we actually havethe heritage of doing that. We have ourcards, right? You've probably seen thecool debit cards. You can customizethem, you can draw on them. And actuallywhen you think about the future ofsoftware development and where it'sgoing with generative UI, there isnothing in the future that's going toprevent us from creating thesecompletely one-of-one experiences. So,that's that's what like is top of mindfor me at the moment. And I do think wewill get there relatively quickly thatevery Cash App does feel unique andcompletely designed around the person.And then from a business perspective,why I think that's super interesting isit creates this like deeper, harder toquantify emotional connection with aproduct that is the same as like yourwardrobe. Clothes are by and large likean expression of personal identity.

00:48:00We've seen a trend particularly inyounger audiences that digital identityis as valuable as physical identity. Youcould just need to look at the Fortnitestore to see the numbers there. So, youknow, I think from my side I have a verydeep belief and a bet that interfaces inthe not too distant future will bebespoke, completely one-of-one, and atleast in Cash App's instance, a completerepresentation of your personalidentity. I I mean like my brain isalready running like, "Man, howapplicable is this to B2B, you know?"Like how far are we going to go intothis?>> It's It's so applicable. I think it is.It's It's so So, my dad he still runsthis a tiny little small businessantique shop, right? And his optionspreviously were he could have his ownlittle website, which was so difficultfor him to manage. Like he's not atechnological guy. He's an antiquedealer for God's sake, right? Like youcan kind of picture it, right? Um or hecould upload to his antiques to likesome big conglomerate that standardizesthe experience and his like personaltouch and his shop and like all of theeffort he puts into it basically justgoes into like this commoditized likeDoorDash esque platform. Like that to meis just like not the future of B2Bsoftware. Likeyou know, if if my dad was able tocreate a completely bespoke, you know,solution and and piece of software thatallowed him to serve

00:49:15his customers andcreate a website that was arepresentation of hisstyle and identity, it would havechanged his entire course of hisbusiness. But he wasn't able to do that.And I genuinely think in the future thatpeople will be able to do that. And evenat Square we're talking with lots ofcustomers at the moment and buildingstuff. And you can kind of see thedirection of travel that people wantvery bespoke interfaces as much for B2Bbecause every restaurant is different.And I just think that's like one of thebiggest opportunities ahead for designin general, which is like how do how doyou make this stuff? And then how do youmake sure it comes together in acohesive way? Creativity as acompetitive advantage regardless ofindustry does feel like it's going tobecome more of a thing. Which that'sthat's exciting as a designer, you know?Because if your if your if your productdoesn't have something that obviouslythere's this bucket of top-downenterprise contracts that they're alwaysgoing to exist, butthere is an abundance of choice and oneof the choices is make it yourself.So,it's got to be good, you know, the barin the same way that you were talkingabout the bar is rising for designers,it also is going to rise forproducts specifically SaaS probably. Ihope so. Maybe I'm wrong. I reallyreally hope so. I just I just thinksoftware was ma- yeah, you had to massproduce it previously essentially and ithad to be

00:50:30one size fits all for almostevery customer and if you were inWorkday and signing a contract for like10 million, you probably got somecustomization to it, but by and largeit's like the same product. And I justthink that whole notion of how softwareis created is is kind of beingchallenged and that to me is just soenergizing. If I didn't believe thatcreativity had a role in this new world,I would quit my job and give up and mywife's an amazing baker, I would justsupport her doing like bakery. Likehonestly, but I genuinely believe thatthe world would be a better place ifmore businesses really led withcreativity and used it as a tool todrive the outcomes at scale and that'sreally what fires me up personally. It'syou know, there's very few I know likethe designer founder trope, there's veryfew designer founders, there's very fewdesigners on boards and I think designis often misconceived as just pixelpushing and it's not. It's like creativeproblem solving. The design industry atlarge can look at problems in a verydifferent way and come at them in a verydifferent way and that's like a skillset that transparently I think wouldmake the world a much better place thantoday where it's like, you know, justgiant conglomerates in every shoppingmall and like not enough neighborhoodbusinesses

00:51:46thriving and uh you know,one-size-fits-all [clears throat]software and mass-produced clones. LikeI think there's an opportunity heregenerally, not to go like toophilosophical, is to like for design tolike push against that tide of the last10 years that it's you know, it's allconglomerates and go back towards moreof like creativity at the heart ofeverything, neighborhood businesses,neighborhood stuff. And And I thinkthat's very, very energizing for me. Isaw something on Twitter, I thinkactually [clears throat] it was lastnight, referred to this as the nicheeconomy. And I'm totally adopting itbecause I think thatit's so relevant for designers becauseeven if we were able to correctlyidentify a problem, which as a whole,like a given the population, we'repretty good at, right? Like that's whatwe do.It didn't really matter because therewas still such an upfront cost and skillgap to actually be able to go and solvethe problem. Where all of a sudden now,it's token cost.>> [laughter]>> And the time cost is driven down. We arenot reliant on other people to actuallygo and solve the problem. So, I do hopethat there are so many design-createdbusinesses that don't necessarily haveto be these billion-dollar companies. Itdoesn't matter, right? It's like it'sthe niche economy. I think the nicheeconomy can be driven by designers andI'm very excited about the future forthat. I love that phrase. And it'salmost like we were saying earlier isbefore we kind of press record, I wastalking

00:53:01about theI think future tech companies might belike CPGs. And it's it's not it's notdissimilar to that where it's likeactually, is it one piece of software in5 years time that serves a billionpeople like Method does or is it splitup into 30 pieces of software that solvemuch smaller niches? So, you go to, youknow, your fitness app is booked here,like your local community is just yourwhere you live. Like that to me feelslike a much more competitive and betterworld, which I hope exists, but it alsocould just not and get eaten. But bythese big by these big AI companies. Butyeah, I think for the good of the world,it would be amazing if it went this way.And I hope design continues to have arole in shaping it, to be honest. Cam,this has been incredibly energizing. Iappreciate you coming on today and giveme a lot to think about and also justlearning more about how you all operateand everything that's going on has beenjust fascinating. So, [music] thanks forcoming on, pulling back the curtain, andtalking with us today. Duly appreciateit and thanks for listening and I hopeit was enjoyable for [music] you guys.Before I let you go, I want to take just1 minute to run you through my favoriteproducts because I'm constantly asked[music] what's in my stack. Framer ishow I build websites. Gen way is how Ido research.

00:54:16Granola is how I take notesduring crit. Jitter is how I animate mydesigns. Lovable is how I build my ideasin code. Mobbin is how I find designinspiration. Paper is how I design likea creative and Raycast is my shortcutevery step of the way. Now, I've handselected these companies so that I cando these episodes full-time. So, by far,the number one way to support the showis to check them out. You can find thefull list at dive.club/partners.