Polly D'Arcy - Going from IC to VP of Design at Wealthsimple

00:00:00I have imposter syndrome every day,still, and I think that means that I amconstantly challenged and growing andtaking on new things. That [music]feeling is just anxiety of like, I don'tknow the answer yet. I don't know whatI'm going to do. But, for me atWealthsimple, it's always been like, Idon't know what I'm going to do, butit's going to take it like day by dayand we're going to figure it out. And Ithink that attitude can take you really,really far. Welcome to Dive Club. Myname is Ridd, and this is wheredesigners never stop learning.Today's episode is with Polly Darcy, whoover a few short years went from an ICat Wealthsimple all the way to head ofdesign and eventually VP of design. So,we're going to do a deep dive into herjourney and everything that she learnedalong the way about design leadership,craft, [music]hiring, and a lot more. So, let's startat the beginning of her story. I joinedWealthsimple almost 7 years ago, back in2019, before COVID, which seems sort ofwild. I joined the team in 2019 as an ICand we're only five people. So, we weresuper small team. We were still like asort of a centralized team within thecompany, cuz I think at the time therewas between like 250 and 500 people. Andso, we weren't even embedded on productteams. We were just like this core groupthat sat together and every day you showup to work and you were working on adifferent part of the product, becausethe product was so much

00:01:15smaller than itis today. And I always knew that Iwanted to lead a team. I grew up playinga lot of sports. This is like a a commonthing for me. I I often lean on sportsanalogies, because not to be a totalcliché, but I am a Canadian gal who grewup playing hockey. So, I feel like I'mconstantly thinking about like what thattaught me and how it impacts sort oflike what I love doing. And so, I alwaysknew I like wanted to lead a team andwork with a team, and that's sort oflike where I get most of my energy andwhat I really enjoy doing. And so, Imoved into this manager role, and I wasmanaging, I think like three people. AndI was just sort of learning the ropes,but super green, super new tomanagement, and, you know, still had noidea what I was really doing. Brett,who's a co-founder at Wealthsimple andour chief product officer, my boss, overthe next sort of 6 months came to mewith thisincredible opportunity. He was like, youknow, I I really see something in youand I think that you should lead thisdesign team. I was like, what?Are you sure?I think as as they talk I was like, thisguy's crazy. I think like I obviouslyhad shown him my potential and that Icould do it, but I think it really feltlike sort of the scary moment where Iwas like, I have no idea what I'm doingand where I'm going to start. Lookingback, I think um something I reallyadmire about Brett and what he's taughtme is like, when you

00:02:30see potential inpeople on your team, you need to givethem opportunities and and support themand and help them grow. Every time yougive somebody an opportunity it's a bet.Like, 50% of the time those bets aregoing to play out and and work reallywell and 50% of the time they might not,but I really love that approach of like,when I work with people and I get energyfrom them and I like see that potential,I you know, I also want to like givethem an opportunity to grow and take onsomething new and challenging and that'swhat Brett gave me and um and sort oflike started my trajectory here. And so,you know, I've been in this role leadingthe design team for I guess like four orfive years now. I remember when I firstcame into the role, someone said thestatement um smooth waters don't makegreat sailors and it just like hit me inthat moment as I was going through thissort of challenging time of figuring outlike my new role at the company and howwe were going to get through it andrebuild the team, that like you have tolive through the tough stuff and figureout how to get through it and if you canmake it, you like come out stronger andbetter and you learn so much in theprocess and I feel like just as ayounger person and more of a, you know,coming from more of an IC lower managerrole, I really like needed to hear that,I think, as like something to motivateme and help me get to the next phase

00:03:45ofmy leadership. And so, it's something II tell people in my personal life whenthey're going through challenges, butalso like at work. it's like it's notalways easy, but like a lot of like thechallenges that you face are really likeopportunities for you to learn somethingnew and and grow in your role and reallyget better. And so that's something Ilike want to instill in my team all ofthe time whenever they're going througha challenging moment. When it came tothe team what we had to do, at the timeour product was not very good. You know,we were growing, but the quality of ourproduct was was nowhere where it neededto be. Like you would open the app andthere would be bugs and it was reallyjanky. And just like the the craft wasnot there. I think like you could tellthat we were not using the product. Thepeople building the product were notusing it. They were not looking at it. Ireally believe that if you as someonewho is a sort of maker and owner of thecompany building this product do notwant to use it with your own money, it'snot good enough. You either have to likecome to us and tell us why it's not goodenough. And but also you have to buy asword action and like take the steps tomake it really great. And you know, likeif you're not going to use it, why wouldanybody else? And so that's when thislike first sort of era began and thefirst big shift we had to make in theculture was all around dogfooding

00:05:00andgetting everybody who is building orselling the product cuz at also boyyou're either building or selling reallyto use the product every day and reallylike become obsessed with it becausethat was going to be the only way wewere going to make it really reallygreat for our customers. And so westarted with the design team and askedthat everybody make sure that they arenot only like literally looking at theapp every day, but you like puttingtheir own money in it. The beauty of ourproduct is like you can open anyaccount, it's free. You can put in adollar, you can put in 10 bucks. And Ijust wanted people to like explore theproduct, use it, open every new account,test every new feature. So they reallyunderstood what our customers wereexperiencing. And then share yourfeedback and like push through what youthink should be better. Because youknow, it's one thing to like testsomething in staging and it's anotherthing to actually like use a productwith your own money because you just youlike are going to like very deeply feelthe the pain points and the friction andand the frustration. And so, the firstshift was all about dogfooding andgetting everybody to really use theproduct. And today, like that has becomea company-wide sort of philosophy andculture where like every new hire I hostan onboarding session with them where Ilike do a live walk-through and tour ofour app, and then we talk about how youdogfood. And as a result, you know, theteam started using the product, andeveryone started

00:06:15just like floodingSlack with all of the feedback that theyhad. Like whether it was like bugs theywere catching or whatever or justfeedback about how to make somethingbetter or a feature that was missing orsomething that didn't make sense. Realquick message and then we can jump backinto it. It's surreal that I can justtalk to my computer before bed and thenagents [music] explore 20 differentconcepts on Paper's canvas that I canreview the next morning to pick adirection. And using Paper to scale myexplorations with AI is totallyreshaping the way that I think about mydesign process. And in the time that itwould take me to make two manualiterations, I can see a design 10, 20different ways on the canvas. And AIalways comes up with something that Ididn't consider. So, I'll just grab myfavorite parts from a handful ofconcepts, start moving things around,making little tweaks, and everythingthat the canvas is really good at.>> [music]>> And then when I'm ready, I can just tellClaude or Codex to build the selectedframe, and there's [music] nothing lostin translation because Paper's canvasalready uses HTML and CSS. And Paper hastruly taken my design process to thenext level. I cannot recommend itenough. Just head to dive.club/paper[music] to start designing today. Allright, Framer just released two killerAI features that I have

00:07:31to tell youabout. The first is wire-framer. You canchat with AI to skip the blank canvas[music] and spark all kinds of ideas.And there's no easier way to spin up aresponsive page with structure andstarter content that's ready to [music]edit. Now, the second feature isworkshop. It's a way to create advancedcomponents using natural language. So,you can spin [music] up all types of newvisual effects, no coding required.[music]It's just another reason why I recommendFramer to absolutely everyone. And youcan start using these features today.[music] Just head to dive.club/framer.

00:08:08Now, back on the episode. I actuallythink that's one of the competitiveadvantages of the teams that we kind ofput on the pedestal and celebrate theircraft is they make these daily use toolsthat they have to use in their own job.It's like there's a reason there's a lotof like design and dev tool teams thatare so well crafted. It's cuz like yeah,you have to use the product every day.So, instilling that in the culture itmakes total sense. I'm kind of curiouslike were there other opportunities thatyou saw in the very beginning or evenjust ways that you know, some of theseocean waves to return to that quote thatI love. Like were other ways that thatshaped the way that you thought aboutwhat effective design leadership shouldeven look like given the fact that youhad very very limited set of experienceup to that time? I think the mostchallenging part of my career so far hasbeen that like step I had to take frombeing a manager of like three people toleading a design team and then you know,being responsible for executing andreally like shifting the culture to makesure we were building the most talentedteam in the world and also likedelivering a product that was reallyexceptional. And I think the only way Igot through that period of feeling somelike self-doubt or uncertainty aboutwhat to do was building really strongrelationships with my product andengineering peers. And there's a reallyinteresting through line here now that

00:09:24I'm reflecting on it to like where weare today with AI tools and how we'restarting to work. But the thing that hashelped me grow the fastest and the mostis sort of like had a come to Jesusmoment about who my first team was. Likewho are the people who I should bespending the most time with and who liketogether as a team we will have thebiggest outsize impact. And I thinkprior to taking on this leadership rolelike I didn't really have a strongrelationship with like a product orengineering partner. And those are thepeople who I'm the closest with now andwho really helped me because they wereable to just sit me down and be like"You're not seeing this thing. Like thisis a blind spot you have and you need togo focus on it and fix it." It's reallydangerous when design operates in a silooutside of product and engineering andthey feel like they have a differentgoal and they don't need to work withthose two groups to be successful. LikeI literally cannot be successful withoutJohn, my VP of engineering. I feel likewe like need to be attached at the hipand making decisions together. And likewe butt heads all the time, but I thinklike having those people to give youfeedback, to bounce ideas off of is soincredibly important. Like comes back tothis idea of a team. We have differenttypes of teams at different altitudes atWell Sub Bot, like I wanted to feel likeevery designer who joins my team is partof a design

00:10:39team.And you have sort of like a culture anda relationship with those people becauseultimately the goal is thatI want the app to feel like it wasdesigned by one hand and not 40. That isincredibly hard to do. It's kind ofimpossible, but that's the goal. And soin order to do that like those 40 peoplegot to be talking to each other and theyneed to know who's working on what andthey have to be collaborating andsharing and trying to sort of build onwhat one another is doing and not feellike they are like going off into theirown silos and doing their own stuff cuzthat's how you ship the org chart. Andso I think I've heard about othercompanies where like as a designer youare part of your product team, but youaren't really part of a design team. AndI want you to feel like you're both partof a design team and a culture there andthen also part of your product team andfeel ownership in sort of like bothplaces. The idea of making the app feellike it's designed by one person I thinkis something that's like so beautiful intheory and yet there's a pretty wide gapbetween like that mandate that you setfor the team and actually getting tothat point and the end product. So, I'mcurious were there any other intentionalprocesses or practices or anything elsethat you feel like you reallyintentionally instilled in theday-to-day, week-to-week practice ofdesign at Wealthsimple to achieve thatgoal? Everybody was sharing

00:11:54all thisfeedback, and then we had no alignmentwithin the organization and then ashared definition of like what qualitywas. So, people were like, "How do Ifigure out what to prioritize and likework on?" And that's when we had tostart defining quality and what it meantfor us at Wealthsimple, like what thebar was. And um a lot of that is donethrough like we literally like created avisual of like a Maslow's hierarchy ofneeds, like a triangle that had thelayers of quality, so that people knowknew like what to tackle first and whereto start. And then like that sharedlanguage sort of permeates throughoutthe organization, and now people are itcan just like more easily align onwhat's important to fix first and sortof like where to begin. Can we getreally specific for a second? Likewhat's on this chart? So, at like thebottom of this diagram is functionality.So,you have to make sure the thing likeliterally works first. And so, that'sreally like built into the spirit of howwe do product development here. Wereally bias towards getting something inour own hands to start using it asquickly as possible. And that means likewe can't be debating in pixels in Figma,which already I know seemed like prettyarchaic given everyone's cloudingeverything. Everyone has like theirfleet of cloud interns. We really like

00:13:09want to I think most often like biastowards building something so that wecan just make sure it works, get a feelfor, you know, the shape of things andhow we want to scope the work. And thenwe need to make sure that it's reliable.You know, we're a financial servicesproduct and company. It's incrediblyimportant that customers deeply trustand can rely on Wealthsimple when itcomes to their money. And so reliabilityis incredibly important to us. And solike those are the foundations that weneed to get right. The third layer beingperformance. So like we need to makesure that it's incredibly like fast andfrictionless to use the product. Notlagging, not slow, not crashing.Um and then it's like how do we make theexperience great? But we onlyreally can really dig into those detailsand make the experience excellent oncethose foundations are in place. And ifwe do it the other way around, it cansort of be a waste of time. And noteverything is this linear. Like it's notas if like we have checkboxes and likebut this is just a framework and sharedlanguage for people to use on theirteams when they are scoping the worktogether and figuring out what'simportant right now. And I think thathas really helped them. And like it'snot always perfect and you know, farfrom it. Be able to say like I don'tthink we should focus on thisimplementation detail yet because likewe need to make it really reliable. Likethat is a helpful trade-off conversationto have.

00:14:25And before it was just likefelt like we were, you know, liketalking to a brick wall. You know,talking past each other and not actuallytrying to like work together to to buildsomething really great. Especially in anorg that I know you all prioritize likethe craft to place a great emphasis onthat. It's really tempting to do thosethings out of order when it iscelebrated. Like I'm assuming there issome level of celebration of craftinternally. What makes Wealthsimple sucha special place to work and be adesigner is that we deeply deeply careabout design and the experience that ourcustomers get. Our brand but also ourproduct experience. The reason thatwe've grown so quickly is becausewe want our customers to feel like thecare that we put into building ourproduct and the attention we we put tothe details is the same is the same careyou put into managing your money. And solike if you open our app and you see abug and you feel like it's janky thenyou're like I don't trust these peoplewith my money. That framing has likereally helped the team I think level upand realize that like oh these likesmall UI bugs really do matter becauseover time they're paper cuts and theywear down that trust battery and peoplewon't stay with Wealthsimple or theywon't join us in the first place becausethey hear that our product is like kindof janky. We want you to feel confidentand like we have your back

00:15:40but also likethere's moments where you can have fun.Uh you know and like you don't have totake life that seriously. Like there'smoments to celebrate, there's momentswhere like I think joy can make such abig difference.Like uh in our in our app on the homescreen you scroll all the way to thebottom we have a 3D coin that you canspin and it's like a fidget spinner. Allyou can do is spin this coin. The numberof people that are coming to our app tospin this coin and it's like people talkabout it on Reddit all the time is liketheir favorite thing is wild but it'slike the moment of levity, you know,you're like opening the app to check themarkets and they have been really wildlately and then you like scroll down andhave this like little moment and fidgetspinner. It's like little moments likethis I think not to jump ahead too muchlike but this is where design is goingto continue to play an outsized role inin delivering a really exceptionalproduct is like we still need humans tolike come up with these like reallycreative and exciting ideas like deeplyconnect to the customer. I'm glad thatyou're entering this conversation fromthe like finance background and that youcan still add a fidget fidget spinner.You know,if you were like representing someprosumer tool it would still be a greatidea but it wouldn't hit as hard as likeyou know, we literally are building theleading finance company in Canada and wehave a fidget spinner and people loveit.

00:16:56So maybe we could talk about thatbucket of opportunities and you know,you talked about the the dog foodingdefining quality really strengtheningthe foundation. My assumption is thatdoes unlock a lot more space to findways to elevate this experience and pushthe craft forward. So what does thatlook like in practice at Wealthsimpleright now? What been really excitingabout these AI tools and like mostlyclothfeel like is what everyone's using atthis point. I find it like reallyhelping designers on my team lean intotheir spike. I've been really enjoyinghearing all these different designleaders a few which you've had on thepodcast talk about how they hire whatthey look for sort of like the makeup oftheir teams a lot of that resonates withme and it's sort of how we operate heretoo. Maybe another lens on top of thatis like this sort of spike philosophywhere you know, I believe that as adesign leader you have to like reallysee people and and understand what theybring to the team that no one else isgoing to bring to the team and we callthat a spike. So whenever we interviewanybody actually like within design orother teamsand we're sort of calibrating you know,like should we hire this person wherewould they fit? We ask what their spikeis and if you cannot name a spike thisperson has and like we're not interestedbecause every single person I we'rerecruiting to this team back to my

00:18:11sports analogies like has got to bringsomething special that's going to helpall of us level up. And if they don'thave that thing then it's like I don't Idon't want to build a team of all thesame people who are good at the samething. It's like not going to help usdeliver the best product experience. Myhusband's a big baseball fan and theseason has begun. You know, you needlike a really great pitcher and a greathitter and like yes sometimes very rareoccasion Shohei type baseball playersare great at both. Those are likeprincipal designers but most of the timelike you want to recruit people I thinkwho are like really good at hitting orreally good at pitching and then youhave to make sure that you can be amatch maker and like find the right roleand team for them. And I think likethat's where the magic really happens. Ithink it's like really dangerous to likeidentify a spike and then put somebodyon a part of the product or a team wherethey can't actually lean into thatthing. Not all teams are equal. Not allteams are working on the same stuff.Some are working on former liketechnical flows or experiences. Some areworking on you know, like a growth teamwhere it is like a lot more like brandfocused a lot of fun a lot of quickexperiments. And so like you wouldn'twant to put someone who's likereally gets joy and energy from workingon like deep technical problem like on agrowth team to do growth experiments cuzthey'd be like, I don't know, this islike not my thing. And vice versa. Andso there's

00:19:26like this matchmakingexercise that happens and iscontinuously happening within the teamthat I think is like super superimportant to like getting the most outof everybody. And what's cool to comeback to these AI tools is likewhat I'm seeing on my own team is thatpeople are using the tool to amplifythat their spike and to like really godeep on the thing you're already reallygreat at. And so, you know, naturallylike for the folks on my team who aremore like design engineering profile,they were already like fairly technicaland maybe they were like and I was adeveloper before or they just like arereally comfortable building like Reactapps or something. They're biasingtowards like prototyping really quicklyand just sort of like leaning into thatand they can build prototypes that maybewe could actually ship. Like the qualityof them is quite good because they knowhow to like sort of I think like reviewthe code and make sure the quality ishigh enough. You know, versus folks whoare like not as technical and that'slike a big ask and leap for them, Ithink. Obviously Claude can help, butlike still we're seeing this challengeof like product and design flooding ourpoor engineers with PRs and they'relike, we don't have time to review themall and like half of them are garbage,you know? This is another topic we canget to. But anyway, so like the moretechnical people being able to do evenmore and then like the folks who arelike more of the visionaries who arelike really leaning

00:20:42into like thebeginning of the design process, stillusing these prototyping tools likevisualize a lot of their ideas superearly or to just like talk to Claude,talk to ChatGPT to like process theirthoughts and like write a better briefand things like that. And so it's likereally cool to see like the differentpoints in the process in which peopleare using the tools. I I don't know theanswer to you know, everyone everyone onTwitter is like trying to tell me whatdesign is now or isn't and whatever andit's like I think I know other peoplehave said this too and I really agree islikeeveryone just has to be really curiousand be digging in and trying stuff andseeing what works for them, but I'm youknow, we're not trying to beprescriptive about what you what toolsyou should be using when, but I getreally excited when peoplecan use it to their advantage and likereally show that like secret sauce theybring to their team or their project orwhatever and that's where like I can seethem naturally wanting to use the toolsand being really excited about them.I want to put a pin into the the PRprocess thing because I do want to touchon that for a second, but first let'sdig into the spike piece a little bitdeeper because something that I hear alot is you know, it's all about howClaude for instance can enhance somebodyhas a little bit of technical curiosityand it's this progression from designersmoving into Claude where it feels likethat is kind

00:21:57of the dominant spike islike how technical do you feelcomfortable being? How much of yourstatement around spikiness isrepresented by that part or thatquadrant or whatever? And maybe do youhave other examples for people who arelistening or like that's not my spike?Like I didn't code before all of thishappened and like yeah, I'm curious, butit's like that's not my spike. I haveother different types of spikes. Do yousee anything else or any other types ofexamples where you could point out andbe like yeah, that's what it looks liketo lean into this moment with AI if youare not somebody who gravitates towardyou know, owning a bunch of the frontend. I think you're sort of thiscombination of like you can lean intoyour existing spike or you can discovera new one. There's a designer on my teamwho leads our options trading experienceand she's an options trader herself.She's an incredible designer. I thinkcuz she just so she so deeplyunderstands the product and thecustomer, she can really lead thatspace, but I think she would tell youshe's like my spike is not like I'm thebest visual designer and the mostcreative I'm never going to come up withlike the most creative wow solution orwhatever. But um I'm going to create areally great options trading experience.And she had a little bit more interestin the technical side of things. But nowshe was just walking us through the factthat she's basically building the entirefront end on her own.

00:23:12And like actually reviewing the code andmaking sure it's the high quality andthrough the process like learning somuch from that, which I know a lot ofpeople are doing. And now I'm like,okay, like she has a new spike. Like shehas a new skill that she is learningthat's really exciting. And it's sort ofinteresting to think about like is thathow we want designers spending theirtime right now? Like understanding codequality and and spending all the timelike fixing and reviewing it so that itis production ready. I don't I don'tknow. I kind of wish an engineer wasjust sitting with you and doing that,you know? Whereas on the other end ofthings like designers who would identifytheir spike as being like very creative,very visual, wanting to spend a lot moretime on crafting those details and likethe last mile, they're like using AI todo very different things. Like help megenerate 3D assets. Help me Help me likeprototype all these like nuanced littledetails, but doesn't have to beproduction ready. It's just helping melike go broad and explore. Like anotherdesigner on my team who's building spendtracking features. You know, we'reworking through this like data vizproblem. And historically, he would feellike he has to design like one or threeoptions in Figma and take all the timeto like, you know, fiddle with thedetails and then like share it back tothe team be like, which data viz isbest? And like with Claude, he's likebuilding a dashboard of every possibledata viz they could use and using

00:24:28mockdata and then feeding in his real dataand he's able to like visualize and makedecisions faster. And so, I don't know.Yeah, I think like regardless of yourspike, you can absolutely be using thesetools. I don't think it's just forpeople who like are trying to build highquality front end or ship high qualityfront ends code to production. What'sreally exciting within the team rightnow is you're trying to figure out theright team structure and both like sizeand like who islike the composition, who's on this teamgiven the new tools and how the rolesand the lines are blurring. Like I thinkthat's really exciting. You know, weused to talk about like two pizza teams.Like, the size of your team, whichdoesn't even make sense. It's like wewould have teams of like eight to 11.I'm like, they need more than twopizzas, I think. Yeah, you you all arehungry as much in Canada.And it's like four pizza teams. But, youknow, that was like the standard and nowwe're talking about what it means tohave a team of three. And maybe it's adesigndesigner and two engineers, maybe it's adesigner and a product person andengineer. Like, I don't even know whatthe makeup of those like who are thosethree people, but I think it's reallyinteresting to think about how we canhave smaller teams who could sittogether, who can move faster with moreconviction, who can really share theroles and responsibilities.Andand like, you know, deliver somethingthey're really proud of and it kind ofcomes back to this idea.

00:25:43This is likethe reflection I was having is like, Ifeel like the reason I've been able togrow and succeed here is therelationship I built with productengineering and how much I've been ableto like learn about their craft and whatthey care about and how they do theirwork and how like the three of us canbuild a really great experience. And so,we're just like now at a place wheremaybe that is just the structure ofevery team and we have more teams withsmaller teams. Like, I don't know theanswer yet, but it's like reallyexciting to think about that and andwhat that would look like. And maybelike the the other end of the spectrummight be that everyone becomes like afull stack or some who does product anddesign and engineering.That one makes me nervous a little bitbecause it's important that we have aleader on a team that has conviction andis like driving the work forward thatlike a team will always make everythingbetter. Like, working with other peopleto challenge your assumptions or yourway of thinking to like contribute tothose ideas. Like, you just need that.And like, I guess some people are sayingthat like Claude is that team now. Like,I think you need humanstill to do that work. I have seenpeople ask Claude to do the thinking forthem and it's like garbage in, garbageout. You you still got to do all thethinking and the strategizing and that'salso been a really interestingreflection I've been having is likespeed has always been our advantage atWild Simple and we always biased to like

00:26:58moving super quickly, but it's withthese AI tools it's like people are areskipping to think and like skipping thedesign altogether which is kind ofdangerous. You know, you have to go slowto go fast. That's still true. Like youhave to spend time in the beginningthinking about what you want to build,having conviction in that, you know,like developing a strong point of view,making sure you have conviction and thenlike spending all of your time of courselike writing the prompt or the MD fileor whatever it is. But like you can'tjust like ask Claude to come up withyour product strategy for you and thenlike go ship it or whatever. You know,which is like kind of what you seesometimes. Someone on my team uses thephrase slop drop with where likesomebody like asks Claude to write a PRDfor them and they just like send it toyou and you're like, I know you did notthink about itPRD, you know?Thinking about that a lot myself toobecause I'm spending way more time incode. Like I I I basically am alwaysusing Claude as the dominant interfaceand then I will use the canvas throughClaude when I need to explore things.Even go back to your original point likewith the spiciness for instance quicktangent is like I'm bad at graphicdesign. I won't even say that it's it'snot a spike. Like I'm actually bad atit. It's not who I am as a designer.Like I'm a little bit more like productfocused, technical. So all of a suddenthe coding world for me is kind ofalmost just turned me into a you know,product minded front end engineer in

00:28:13some ways. But when it comes to making awebsite and you know, a little graphics,actually I was texting Tiago and belike, dude, what do I do here?You know, I'm like that's not that's notme. That's not I don't know how to makea graphic to represent an idea thatisn't you know, in my nice little CSSbox. So I'll then have Claude withabsolutely no thought whatsoever upfront just be like, can you just dump abunch of ideas? And then I'll look atthem like, oh, 4B is interesting. Let'sdo five more like that. And and I don'ttouch a single pixel and I'll get like agraphic design that that want and ithelps me as somebody who was maybepreviously a three out of 10 get to likea six or a seven out of 10, which isgreat.From the product standpoint though, formyself and probably a lot of peoplelistening like we are kind of stillfiguring out like what is the deepthinking part of the process up frontbecause so much of the deep thinkingtraditionally happened because it tooktime and there was friction to do thingsand you had to go through all of thesteps and your brain is naturallyprocessing through that. Where now it'slike I have a feature ideaand I can spit that thing out and sendan engineer a very sloppy PR in like 90minutes. And how do we preserve whatmakes designers really good criticalthinkers in that process?

00:29:28I don't know.I I it's not even a question. Idefinitely don't have the answer, but Ithink it's something that at least formyself I'm I'm I'm really playing withright now.>> When everybody can build anything, itbecomes super clear who has greatjudgment and who doesn't. And that's whyI think everyone has sort of started totalk about this idea of like judgmentand taste being everyone's spike I guessand like skill so that they need to leaninto. And make sure you just like yeah,really use your strong judgment andintuition. Which has always been a bigpart of how we build product here. Wethink speed is incredibly important anda lot of building product is justintuition and judgment and like takingbets and getting your product in thehands of customers quickly to see howthey react and the feedback they giveyou. We need to like find more people atWall Simple. I think we have created ateam and a culture where like that thatjudgment is really strong. But a lot ofthat is also like about culture and likehow you help people understand thebusiness and the customer and thenwhat's really important and understandthe shared definition of quality so thatif they do want to go run and buildsomething on their own, they like knowwhat the boundaries are and what the baris.Um sort [music] of interesting. There'sone question that I can't stop askingmyself. What if companies applied totalk to you rather than the other wayaround?>> [music]>> And that question is the foundation

00:30:44forthe all new Dive Talent Network, and[music] it's working. Like, right now,I'm helping 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 you wantto get on my list, or maybe you're evenlooking for your next design hire, headto dive.club/talentto join today.Let's talk about craft for a second.We've touched on it. I kind of want togo a little bit deeper,>> [music]>> and maybe speak to the person listeningwho's very familiar with the bar thatyou all have set at Wealthsimple, and islooking for ways to reverse engineer itin their own org, or in their ownindividual practice. I guess I'm kind ofcurious, like, when you think about whathas led to your ability to consistentlycrank out really well-crafted productexperiences, how much of it isjust hiring the right people andtrusting them to do it, versus moreintentional ways of working, processes,quality checks, like, anything else youall are doing in the the practice ofdesign at Wealthsimple in order toconsistently hit that bar? I would sayit's a combination of a few of thosethings. The most important one being yougot to hire really talented people andtrust them to do a great job, get out oftheir way, and let themrun, you know? And that's

00:31:59the experienceI've had with Thiago. Like, Thiagojoined our team with, say, the end oflast year. We've seen such a a big jumpin the quality of our product experiencebecause we found a great leader who canhelp,I think, execute on that vision that hehas, but also, like, work with our teamto coach other people and get themthere, and I think it's really importantthat you build a team where you havethose, like, really exceptional craftleaders who can help bring everybodyelsealong and raise the bar for everybody.That has been the biggest unlock for me,personally, and what I've seen on ourteam. Like, you have to make those biginvestments in people. I think, alsolike when you when you bring on thattalent, it's sort of like infectious.The way they show up, the stuff theycare about, um the things they'resharing is inspiration. It's likecreated this culture that feels likethere's a lot of energy behind it andeverybody is sharing what they'reinspired by. I think back to a few yearsago when it felt like we were missingthat magic within the design team. Likepeople weren't inspired. They weren'tsharing things with one another. Theyweren't talking to one another and likereally like celebrating one another'swork. And I think you just like over thetime have to really build that cultureand it's not one person. It's it's allof the leaders really like encouragingit, but like bringing

00:33:15in the right typeof people. Like I always come back tothis. Again, it's like what this won'tstop. Like you have to put so much timeand energy into building the right teamand making sure that you have greatchemistry and that you have a sort oflike diverse skill set and experiencelevels too. And uh it's an art and ascience, I think. But I feel reallyproud of the team we've built, but it'staken us many years get here, right?Like it's not you can't do it overnight.You know it when you see it and you feelit and you see you know the result inthe product. Having said that, you know,there's more than Tiago on my team.There's so many talented designers. LikeI I want every person on the team tofeel like they're the A player, too. Andso we have a number of differentdesigners again who are like reallygreat at different things. So what'sinteresting with Tiago, this analogy wasshared by another principal on the teamthat we all laughed at and loved, islike Tiago's spike is absolutely likethe finishing touch, the magic that headds to every single experience. It'slike you just know when Tiago has workedon it. The analogy that a team memberused is like when you're in a kitchenand working on the line, the person whois plating the food with the tweezersand adding like the final flower petalor whatever to make sure it looksexceptional before it goes out, likethat is Tiago, you know? Like that iswhat he is so so great

00:34:30at. And so how dowe set Tiago up for success where likehe can really focus on doing that workand he doesn't have to worry about maybeother stuff that other designers wouldwork on or whatever. Like that's anotherexample of like how do we play to thespike? And yeah, he's just soexceptional at that part of the craft.And then we have another principal,Justin, who is like the visionary. Andso, if you come to him and you're like,I want to build something that's likeearly days, something ambitious you wantto build, you don't know what theexperience should be, and you go toJustin and you're like, let's get theteam excited show not tell, like can wemock up some ideas for what this wouldbe? And like 24 hours later, he's goingto like blow you away with all theseideas and share them with you. Those arevery different strengths. And so, tocome back to your original question twoof like, how do you think about buildinga team and really like fostering, Ithink a culture of like creativity andwanting everyone to be an A player andlike do your best work, it's alsorealizing that like not everyone has tobe a generalist. And like the way youorganize your team doesn't have to beevery designer is embedded on a productteam and they work on their thing andlike they have to do it all. Like it'ssort of how we operated for a long time,but I think having a player coach model,not just with like you and your manager,but like you and other IC's on the team,can one designer work on a project andthen Thiago comes in at the end toreally help them like make

00:35:45the detailsreally excellent before we ship it andlike finesse, you know, and add likereally exciting motion and have fun witha couple of the details. Like that sortof model, too, can work. Think there'slike no one right way of doing it, but Itry and give my team freedom to trystuff. Like whatever's going to work foryou and your team, like you can you canexperiment and see what model is goingto be the most successful. And again,especially with these new like AI toolsand ways of working, like all that'sthrown out the window, you know? LikeThiago works on a team with twoengineers and no product person cuz likethey don't need one. Why not? Well, Iwouldn't be adding a product person ifwe don't. If we don't need you on theteam, that's okay. But would you want adifferent project where you'd be morehelpful? Not every team has to have thesame composition of people and skillsets, which I think has been a bigunlock for for me and how I think aboutlike designing an org. It's probablyinspirational for people listening tobecauseuh sentiment that has popped up multipletimes on this show is, you know, powerto the generalist kind of thing,especially in the AI area. We wantgeneralists, we want generalists. Like,actually your take on we want peoplethat really really spike on one thing. Ido think it's maybe a minority take in away that is refreshing. Okay.>> And I like having it because sometimes Ialmost feel bad for people who areearlier in their career. It's like,well, we want generalists who can owneverything end to end and oh yeah, youneed to be able to code and do productsand

00:37:00like we're all going to wear all ofthe hats and you have to be able to wearall of them to get your next job. Myopinion of this is always sort ofevolving and changing, but it it sort offeels like when you're coming up in yourcareer as a designer, you have to startas a generalist. It's like people usedto say to me like, you should go work ata bunch of different companies, atdifferent agencies, at different productcompanies to like understand what youlike. Like the samethe same idea. Like you should start asa generalist so you can identify thespike. Like what is the thing you'regoing to bring to the team that nobodyelse can bring that you're soexceptional at? That like you get energyfrom and can really lean into. And likeI really believe everyone has a spike,you know? You just may have to likediscover what it is and maybe it changesover time, too. Maybe you got like twospikes, I don't know. Like I think yousaid you're like a product-mindedengineer or whatever. Like that's aspike. Part of it is like admitting whatyou're not good at. Admit this thingthat you're like, I'm never going to bethe best as he said, graphic designer.But I'm really good at product strategyand I like really excited about digginginto, you know, front end or whatever,like code now and and being able tobuild stuff on my own. That is what setspeople apart in my mind and where I'veseen people really succeed. Obviously,nothing is black and white and supersimple. So I would imagine there'sprobably this situation where maybe youas the hiring manager are trying to makesense of who to bring on where you know,somebody

00:38:16has a really interesting spikeand set of skills, but limited domainexpertise. Whereas, you might haveanother person on the flip side that islike that options trader who's like, I know this stuff. I have so manythoughts. I've made all the mistakesalready for years.How do you reconcile those two types ofdesigners when you're trying to decidewho to bring on the team? That's such agood question and we talk about thisconstantly. I think we've learned overtime where we need the subject matterexpertise and where that outweighslike the craft sort of thing. So,actually options is a good example. Likewe learned over time. We had a coupleother people working on it. We're like,we need an options trader building thisexperience. That's how we're going tomove quickly and how we're going tobuild something really great. It's areally tough space to sort of like on onboard onto if you're not an activetrader and you don't like immediatelysort of get it. Then there's so manyother parts of the product where Iactually think you don't have to jointhe team how like actually crypto. Likewe are hiring folks to work on thecrypto product and just from experiencelike I don't actually think a designerhas to like be a D gen crypto trader orwhatever to go build a great cryptoexperience. It's just what I've seen andand observed.Um and so I think

00:39:31we're reallythoughtful about like weighing thosesort of pros and cons identifying whatwe need at that time for that team. Butthere's absolutely no one like rightanswer to that question. Um it's justdefinitely based onthe product, the like the existing teamwho who like who are the players in theteam already and what do you feel likeis missing and that you need. But youknow, it's like this is very simple butsometimes I've seen some leaders on myteam build their team and have playersthat are all good at the same stuff. Soit's like you hire a team of fivedesigners and they're all like reallygood like systems thinkers and are likevery technical. But like as a result theUX UI design is very boring. And becauselike they're just not like those visualdesigners who are going to like thinkcreatively and about like, you know, Idon't know. They just like are missingthe creativity ease and that extrapolish. And so immediately I can saylike you're missing this skill set onyour team and so you need to think abouthow you're going to balance it. It'sjust like constant conversation and backand forth and we're always hiring andteams are changing and whatever. I'm abeliever in small teams. Like I want tokeep my team as small as possible andthat's because I just have seen thatsmaller teams are more effective. Havingsaid that, my design team is now like 35people, which feels massive to me. Andso coming back to this idea that we wantthe app to feel like it was designed byone hand. I think it

00:40:46is super importantthat people are aware of what's going onand like communication just becomesincreasingly important. So, you know, inorder to like move quickly and not slowdown by bureaucracy or other teams orneeding to get buy-in or needing toshare everything. Like you just have tolike proactively communicate reallywell. And so we have had a couplerituals in place within the team, withinthe design team, where people are justregularly sharing what they're workingon. So like every other week, a domain,we have four domains within the org.Banking is one domain for for example.Um they will come and as a team presentthe latest work to the rest of like thedesign leadership group, which isprincipal engineers and directors.And it's purely for visibility and tolike talk about the stuff they'reworking onbecausewe're in such close quarters. We're alldesigning like the same house, you know?We're all just like sometimes indifferent rooms and I I don't want it tofeel like we're all confined in our ownrooms and designing in those rooms andthen like everyone comes out and they'relike, "Oh god, we have differentaesthetics in all these rooms. Like allthese different interior designers, youknow?" Like we have to make sure we'relike seeing the opportunities to connectthe ecosystem and make the experiencebetter. Sometimes you're working on sortof like the same things but differentand just like having that visibility Ithink has really really helped. And

00:42:01I'msure people are would be thinking like,"Can you do that async? Like why do youhave to get together and talk about itin person?" It's like cuz you still haveto talk about stuff. But like yes, wecould do this all on Slack, but I'm abig believer that like you still got getin a room and talk things through withone another and have a conversation. Andso every other week each domain comesand presents that work and it's anopportunity for all the other leaders tobe in the know of like what people aredoing and you know, often we'll talkabout the craft and we'll talk aboutpatterns that are emerging and like oh,what do we want to do about XYZ or likeoh, I love what you're doing here. I'mgoing to bring that back to my team andthat like cross-pollination is soimportant. And then also like everydesigner like knows every other leaderon the team, too. But I just generallyfeel like my design team though 35people now like we all really know eachother and I think that is so soimportant especially cuz we're remote.We also get people together in personbecause I think the only way to likereally feel like you're part of a teamand and be productive is like reallyknow people and spend time with them.Like sometimes I have on-sites andpeople are like what's the point of theon-site? I'm like to just spend timetogether. Don't overthink it. Like getin a room together for a couple days andjust like build together and get to knowone another and talk and like shareideas and it's always productive. It isnever not productive. There's like ananticipation around it, too. Like I'veonly worked remote for

00:43:16a very long timenow and so I typically will be on a teamwhere maybe you have like a quarterlyoffsite or in a past role we had liketwice a year we'd have the entirecompany and then oscillating quarters wewould have just the product team forinstance. Yeah. And like kind ofeverybody gets hyped, you know? You'relike you you want to bring your best.You you want to like tap into thecreativity and I feel like theexpectations are always higher for likewhat we're going to accomplish or thinkabout or the conversations that we'regoing to have in those weeks and so alot of my favorite design ideas thatI've had have come from offsites. 100%>> The vibe's different, you know? Likeyou're just you're coming into it from adifferent posture. Yeah, and like goingback to this point I made earlier aboutthe thing that helped me growthe most and really quickly was buildinga relationship with my product andengineering peers. Like my our bossBrett a few years ago we started hostingthese on-sites where he would bring theentire sort of like product leadershipteam together. And we would have theseon-sites together and we would go todinner together. And like over theyears, all of the importantconversations are happening at dinner.We've covered a lot of ground, but Iwant to make sure that we're we'regetting everything here. Because in thelast few years, you honestly have kindof been forming your design leadershipphilosophy from scratch, right? So likeif we imagine it almost as

00:44:31a book thatyou are depositing little insights orlearnings into, are there chapters thatwe haven't talked about yet that youthink are indicative of who you are as adesign leader and some of the thingsthat you've learned on this ascent? Onething that I do keep coming back to thatBrett has instilled in me is you have tohire people that you would want to workfor. When I like think deeply about thepeople on my team, I actually want tothink about like would I want to reportto this person? You should be able tohire really strong talent and feel likeyou can trust them to go do the work anddo it really well. And when you don'thave that trust, it's cuz you like don'thave the confidence and they're justlike not strong enough. And so,um it is all about like building thisreally strong team underneath you Ithink to be successful. That was a bigunlock for me that took longer than Iwanted it to.Um but it's also like just like it'ssomething I see every day. Think likereflecting on that is really important.What are the signals that you would lookfor even in like a portfoliopresentation or a conversation with acandidate that would get you to thepoint where you would have that level ofconviction where you would want toactually make them an offer. Maybe evenreflect on the the last few designersyou've hired. Like what were thespecific points in time where you'relike, "Yep, you're a yes now." Hiring isreally challenging and we're sort ofconstantly adapting our hiring processto make sure

00:45:46we can get the rightsignals when we're interviewing people.So, you know, we have a portfoliointerview, which every company does, andyou show up, you have your buttoned-uppresentation, you got a script, you'relike ready to go and feel rehearsed, andyou can share the work. But what we havefound over time is that it's reallyhelpful to get people off script and seehow they react and how they think ontheir feet. And that's going to give youa much more accurate idea of like whatis it like to actually work with thisperson day-to-day. And so we introduceda new interview that's an app reviewwhere we ask you to open an app on yourphone. We don't tell you what it isahead of time and do like a live crit ofthe app. Fun. We've been choosingSpotify. I can say that now because likewe're going to change it. This interviewhas been so incredibly helpful becauseit has gone like in every direction youcan imagine. Like when we were we had apoint where we were like, what even issuccessful in this interview? And liketook us a while to figure out what wewere even looking for because everyperson treats it so differently. It's soopen-ended. But I think the mostsuccessful versions of that interviewhave been people who are like diving inand are so enthusiastic and like have somany ideas and are really opinionatedand they can sort of like go high-leveland then go into the weeds and sort ofcomment on those and they're talking

00:47:01about the things they love and thethings they don't love. And it's it'stough. Like I I it's a intimidatinginterview and some people I think getlike flustered and stuck and I totallyrelate to that. But the most successfulversions of it have been people who arelike taking a beat to be like, okay, Iwant to like do a tour of this app. Iwant to talk about all the things thatI'm like reacting to and seeing and likewhat's resonating with me. And I thinkjust like really getting a feel for likehow people think has been really helpfulto us. Ultimately like we want peoplewith like really strong opinions.Like I don't want anyone on my team whodoesn't have a strong opinion, who canget gain conviction and idea and likemove it forward. Like everyone is aleader and that's like a leadershipquality we look for in everybodyregardless of what level you're at orwhat role you're in. The other thing Ilove that people do in the interviewprocess and that I find is always apositive signal is when you're having aconversation with them, whether it'slike a hiring manager interview or evenin the middle of a portfolio review somepeople have done this. When somebodyasks a question and they want to godeeper on a project. We've seen peoplesay like, "I'll just open the Figma andshow you." They like open their Figmaand they're just like walking around intheir Figma or not walking around, butyou know, they're like showing you theirFigma file and digging into stuff.There's something about the like rawnessof that, you know, it's like notscripted and they're just like, "Let mejust show you like what my work actuallylooks like and and

00:48:17all the differentthings that I sort of explored orwhatever." That like gets us closer towhat it would actually be like to workwith you and I love when those momentshappen. Cuz yeah, I just like want toget to know the person too in in theprocess. Is the deck still the rightlaunching point? Like if somebody cameup if somebody started the conversationand they just open up the Figma. Stillpositive or now is it messy? Okay,that's what I thought. Yeah, just makingjust making sure.>> [laughter]>> I think presentations they're absolutelyrequired because we want you to havestructure to how you walk through thework. Storytelling is so important andmaking sure, you know, succinctly likewalk walk us through your journey andwhat you've been working on, but there'sjust these like off-the-cuff momentsthat I appreciate. Like I appreciatehonesty and just getting a feel for likewhat what does it look like? A peekbehind the curtain, you know, like whatdoes your Figma file actually look like?We're not like, you know, over-indexingon that, but it does feel like it'sconsistently a good signal I find. I hada hiring manager that I worked with andthat was his entire approach wasbasically to get someone, like you said,off script and then have them be able totalk effectively at minute detailsbehind the decision. Like he had to havepart of the evaluation happen at themicroscopic level and it was with thatpairing of storytelling that that likethose are the two ends of the spectrumthat he was evaluating. So, I get themicroscopic level.Maybe really quickly

00:49:32can we touch on thestorytelling piece and just imagine thatsomebody is listening and they have aportfolio presentation tomorrow andthey're looking for little tactics or orsomething that maybe you've seen as ahiring manager with like, "Wow, that wasgood. Like that actually stood out fromthe sea of portfolio presentations thatI'm sitting in front of." I think whatmake portfolio reviews and presentationsso challenging is finding the rightaltitude to present the work at and likebalancing the like how do I tell thebigger picture or how do I give them asense of the bigger picture, but alsoshow them the details.And I find often folks miss out onshowing the details, but when we'reassessing your like that's what we'reassessing. And so I actually find that alot of folks are really great at thestorytelling part. Like here's myjourney at this company, here's theproblems we've been solving, here arethe steps in my process, here's theresults, here's what we learned and howit performed and whatever. But that'swhy I get excited about people pullingup Figma cuz it's like I want you toshow me can you like share your phonescreen with us and walk through like thething you shipped in prod and like talkabout what you love about it, what youdon't love about it. You know, so oftenwhat we design in Figma is not actuallywhat makes it to production. Like talkabout that and that sort of process. Diginto the

00:50:47details and talk about how youdesigned this interaction, this likemoment and why you spend so much time onit. A lot of people actually like showstatic Figma stuff in theirpresentation, which I feel like isunacceptable at this this the stagewe're at.It's like we got to see prototypes. Youwant to I want to see how this feels andyou know, how you make trade-offs anddecisions. It's funny to me actuallythat nobody or I haven't seen anybody umactually like open the products they'vebeen working on in production and andtalk about like the thing that theydesigned and built. Kind of strange, eh?I don't know if I've ever seen thateither. Yeah, but it's like why not?Like this is the thing you literallydesigned and built with your team.There's no better flex than to like showsomething and clicking through it andit's good. Like this is a live demo ofthe thing that I built. Um I think thatwould be huge. You know, we don't haveinfinite amount of time in thesereviews, but folks often stop at thelike and then we shipped it and this ishow it performed. What happened then?Like did you keep iterating on it andmaking it better or like you know, whatdid you learn 5 months down the road?Like maybe some folks don't have theopportunity to keep working on the sameproject or whatever, but so much of whatwe do at Well Simple is iterating andkeeping like building on an experience.You learn so much over time and itevolves so much over time. And we loveinternally talking about the evolutionof our products

00:52:03and seeing where theystarted from and like how great they gotand how shitty they were at thebeginning, you know? I find folks aren'tusually talking about that evolution.It's just like a linear like and then weshipped this thing and there's a lot oftension that lies in the like iterationand and a lot of learning and like funstuff that comes out of that, too. It'snot just like you design something fromzero to one, you know? And it's notrepresentative of even how teams areworking as much anymore. You know, likethe the the the the giant process at thebeginning is kind of fading towards thequick ship, be decisive, and theniterate obsessively.>> Yeah. Yeah, I think I think people feelpressured to come up to Actually, Imean, I see this less now. It's like 5years ago, but you know, people wouldshow up to an interview and be like,"Here's the double diamond." Like whenhas anyone ever followed the doublediamond?You know, like be honest with me.Like how are you actually working?There's something performative aboutthat and I would rather people just behonest about like this is how we work atthe place I'm at. It's not necessarilylike what I believe to be the only wayto work, but like this is how we'rebuilding and shipping and what I'mlearning throughout the process. Like Ithink some people expect or thinkthere's like one way to do design andthey have to show that they know thatone way, you know? Okay, final partingquestion before I let you go here. And Iagain, I kind of just want to speak to avery specific listener who I don't know,maybe they did just get a promotion ormaybe they got a new role or maybethey're working on a project that's

00:53:18stretching them and they're feeling alevel of impostor syndrome that isslightly foreign and not really sure howto feel about that and what to do withit. And listening to your story, I'msure that there were moments in timewhere you just felt like, "Whoa, like Iam in front of my skis right now and I'mcurious if you have any parting thoughtsfor that listener before I let you go."I have impostor syndrome every day,still, and I think that means that I amconstantly challenged and growing andtaking on new things. And I think if youdon't feel that, then you probably suckand you're not doing enough to grow, andyou need to be more ambitious andchallenge yourself. That feeling is justthe anxiety of like, I don't know theanswer yet. I don't know what I'm goingto do. But for me, it's also always beenlike, I don't know what I'm going to do,but it's going to take it like day byday and we're going to figure it out.And I think that attitude can take youreally really far, but also like ask forhelp. Like I I find so many people thinkthey have to solve these problems ontheir own, and I know that some roles itcan feel isolating, like maybe you don'tknow who to go to, but again, like Ihave felt leaning on my product andengineering counterparts to ask them forfeedback and help has unlocked so muchfor me. You need to find people who canbe real with you and are actually goingto tell you like what you

00:54:33need to changeand do better, cuz that's the only wayyou know, you're going to get better. Umand that I feel very lucky that I foundthose people, but you got to seek thosepeople out and build those relationshipsand then I think it's really rewardingand and you will do the same for them,too. All right. I'm sure this podcasthas been super helpful for a lot ofpeople, so really, really appreciate youcoming on and sharing a little bit aboutyour experience,all of the the ups and downs, whatyou're learning and then also justadapting to this moment in time. It'sbeen a fantastic conversation [music]and I'm just appreciative that you cameon, so thank you. Thank you so much.Thank you for having me.