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

[00:00] I have imposter syndrome every day still, and I think that means that I am constantly challenged and growing and taking on new things. That feeling is just the anxiety of like, I don't know the answer yet. I don't know what I'm going to do. But for me, also, Bullitt's always been like, I don't know what I'm going to do, but it's going to take it like day by day and we're going to figure it out. And I think that attitude can take you really, really far. Welcome to Dive Club.

My name is Ridd, and this is where designers never stop learning. Today's episode is with [00:30] short years went from an IC at Wealthsimple all the way to head of design and eventually VP of design. So we're going to do a deep dive into her journey and everything that she learned along the way about design leadership, craft, hiring, and a lot more. So let's start at the beginning of her story. I joined Wealthsimple almost seven years ago, back in 2019, before COVID, which seems sort of wild. I joined the team in 2019 as an IC, and we were only five people [00:58] So we were a super small team.

We were still like sort of a centralized team within the company industry. [01:03] Because I think at the time there was between like 250 and 500 people. And so we weren't even embedded on product teams. We were just like this core group that sat together and every day you show up to work and you're working on a different part of the product. [01:14] Because the product is so much smaller than it is today. And I always knew that I wanted to lead a team. I grew up playing a lot of sports.

This is like a common thing for me. I often lean on sports analogies because not to be a total cliche, but I am a Canadian gal who grew up playing hockey. So I feel like I'm constantly thinking about like what that taught me and how it impacts sort of like what I love doing. And so I always knew I like wanted to lead a team and work with the team. And that's sort of like where I get most of my energy and what I really enjoy doing. [01:44] managing, I think like three people.

And I was just sort of learning the ropes, but super green, super new to management. [01:50] And, you know, still had no idea what I was doing. [01:52] Really doing. Brett, who's a co-founder at WellSimple and our chief product officer, my boss, over the next sort of six months came to me with this [02:00] incredible opportunity. He was like, you know, I, I really see something in you. And I think that you should lead this design team. [02:06] I was like, what? [02:08] Are you sure? [02:10] I think at the time I was like, this guy's crazy.

I think like I obviously had shown him my potential and then I could do it. But I think it really felt like sort of the scary moment where I was like, I have no idea what I'm doing and where I'm going to start. [02:40] Like 50% of the time those bets are going to play out and work really well and 50% of the time they might not. [02:46] But I really love that approach of like when I work with people and I get energy from them and I like see that potential.

I, you know, I also want to like give them an opportunity to grow and take on something new and challenging and, you know, [02:57] That's what Brett gave me and sort of like started my trajectory here. [03:01] And so, you know, I've been in this role leading the design team for, I guess, like four or five years now. I remember when I first came into the role, someone said the statement, smooth waters don't make great sailors. [03:13] And it just like hit me in that moment as I was going through this journey.

[03:18] sort of challenging time of figuring out like my new role, the company and how we were going to get through it and rebuild a team that like you have to live through the tough stuff. [03:26] and figure out how to get through it. And if you can make it, you like come out stronger and better, and you learn so much in the process. And I feel like just as a younger person, and [03:36] more of a, you know, coming from more of an IC lower manager role. I really like needed to hear that, I think as like something to motivate me and help me get to the next phase of my leadership.

[03:46] And so it's something I... [03:48] Tell... [03:49] people in my personal life when they're going through challenges, but also like at work. It's like it's not always easy, but like a lot of like the challenges that you face are really like opportunities for you to learn something new and and grow in your role and really get better. And so it's something I like want to instill in my team all the time whenever they're going through a challenging moment. When it came to the team and what we had to do at the time, our product.

[04:10] was not very good. You know, we were growing, but the quality of our product was nowhere where it needed to be. Like you would open the app and there would be bugs and it was really janky. [04:20] and just like the craft was not there, I think like you could tell that we were not using the product. The people building the product were not using it. They were not looking at it. I really believe that [04:32] If you, as someone who is a sort of maker and owner of the company building this product, [04:37] Do not want to use it with your own money.

It's not good enough. [04:41] You either have to like come to us and tell us why it's not good enough. And but also you have to buy a sword action and like take the steps to make it really great. And, you know, like if you're not going to use it, why would anybody else? And so that's when this like first sort of. [04:55] era began and the first big shift we had to make in the culture was all around dog fooding and getting everybody who is building or selling the product because at Walsamble you're either building or selling really to use the product every day and really like become obsessed with it because that was going to be the only way we were going to make it really really great for our customers.

[05:14] And so we started with the design team and asked that everybody make sure that they are not only like literally looking at the app every day, but like putting their own money in it. [05:23] The beauty of our product is like you can open any account. It's free. You can put in a dollar. You can put in 10 bucks. And I just wanted people to like explore the product, use it, open every new account, test every new feature. [05:34] So they really understood what our customers were experiencing. And then [05:39] Share your feedback and like push for what you think should be better because, you know, [05:43] It's one thing to test something in staging, and it's another thing to actually use a product with your own money because you are...

[05:50] going to like very deeply feel the pain points and the friction and the frustration. And so the first shift is all about dog fooding and getting everybody to really use the product. And today, like that has become a company wide. [06:02] sort of philosophy and culture where like every new hire, I host an onboarding session with them where I like do a live walk through a tour of our app. And then we talk about how you dog food. [06:11] And as a result, [06:12] you know, the team started using the product and everyone started just like flooding slack with all of the feedback that they had.

Like whether it was like bugs they were catching or whatever, or... [06:22] Just feedback about how to make something better or a feature that was missing or something that didn't make sense. Real quick message and then we can jump back into it. It's surreal that I can just talk to my computer before bed and then agents explore 20 different concepts on paper's canvas that I can review the next morning to pick a direction. And using paper to scale my explorations with AI is totally reshaping the way that I think about my design process.

[06:52] different ways on the canvas and AI always comes up with something that I didn't consider. So I'll just grab my favorite parts from a handful of concepts, start moving things around, making little tweaks, everything that the canvas is really good at. And then when I'm ready, I can just tell Claude or Codex to build the selected frame and there's nothing lost in translation because paper's canvas already uses HTML and CSS. Paper has truly taken my design process to the next level. [07:22] recommended enough, just head to club slash paper to start designing today.

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When you can start using these features today, just head to club slash Framer. Now on to the episode. I actually think that's one of the competitive advantages of the teams that we kind of put on the pedestal and celebrate their craft is they make these daily use tools that they have to use in their own job. [08:22] that are so well-crafted. [08:24] It's because, again, you have to use the product every day. So instilling that in the culture, it makes total sense. I'm kind of curious. [08:30] Like, were there other opportunities that you saw in the very beginning or even just ways that some of these ocean waves to return to that quote that I love?

Like, were other ways that that shaped the way that you thought about what effective design leadership should even look like, given the fact that you had a very, very limited set of experience up to that time? [09:00] and then, you know, being responsible for executing and really like shifting the culture to make sure we were... [09:06] building the most talented team in the world and also like delivering a product that was really exceptional. [09:11] And I think the only way I got through that period of feeling some like self-doubt or uncertainty about what to do was.

[09:17] building really strong relationships with my product and engineering peers. And there's a really interesting through line here now that I'm reflecting on it to like where we are today with AI tools and how we're starting to work. [09:28] But [09:29] The thing that has helped me grow the fastest and the most is... [09:33] sort of like I had a come to Jesus moment about who my first team was like, [09:37] who are the people who I should be spending the most time with and who like together as a team, we will have the biggest outsized impact and, [09:44] And, yeah.

[09:45] I think prior to taking on this leadership role, like I didn't really have a strong relationship with like a product or engineering partner. [09:51] And [09:52] Those are the people who... [09:54] I'm the closest with now and who really helped me because they were able to just sit me down and be like, [09:59] You're not seeing... [10:01] this thing. This is a blind spot you have and you need to go focus on it and fix it. I think it's really dangerous when design operates in a silo outside of product and engineering and they feel like they have a different goal and they don't need to work with those two groups to be successful.

I literally cannot be successful without John, my VP of engineering. I feel like we need to be attached at the hip. [10:19] and making decisions together. And like we butt heads all the time. But I think like having those people to give you feedback, to bounce ideas off of, [10:27] is so incredibly important. It, like, comes back to this idea of a team. We have different types of teams at different altitudes at Wells' Bowl. Like, [10:35] I wanted to feel like every designer who joins my team is part of a design team.

[10:40] And you have... [10:41] sort of like a culture and a relationship with those people, because ultimately the goal is that [10:47] I want the app to feel like it was designed by one hand and not 40. That is incredibly hard to do. [10:53] It's kind of impossible. [10:55] But that's the goal. And so in order to do that, like those 40 people got to be talking to each other and they need to know who's working on what and they have to be collaborating and sharing and trying to sort of build on what one another is doing and not feel like they are like going off into their own silos and doing their own stuff because that's going to ship the org chart.

[11:12] And so I think I've heard about other companies where like, [11:15] As a designer, you are part of your product team, but you aren't really part of a design team. And I want you to feel like you're both part of a design team and a culture there and then also part of your product team and feel ownership in sort of like both places. [11:26] The idea of making the app feel like it's designed by one person, I think, is something that's so beautiful in theory. And yet there's a pretty wide gap between like that.

[11:35] mandate that you set for the team and actually getting to that point and the end product. So I'm curious, were there any other intentional... [11:42] processes or practices or anything else that you feel like you really intentionally instilled in the day-to-day, week-to-week practice of design at Wealthsimple to achieve that goal? [11:53] Everybody was sharing all this feedback. [11:55] And then [11:56] We had no... [11:58] alignment within the organization and a shared definition of like what quality was. So people were like, how do I figure out what to prioritize and like work on?

[12:06] And that's when we had to start defining quality and what it meant for us. And I will simple like what the bar was. [12:11] And a lot of that is done through like we literally like created a visual of like a Maslow's hierarchy of needs, like a triangle that had the layers of quality so that people know knew like what to tackle first and where to start. [12:25] And then like that shared language sort of permeates throughout the organization. And now people are... [12:30] It can just more easily align on what's important to fix first and sort of like where to begin.

Can we get really specific for a second? Like what's on this chart? So at like the bottom of this diagram... [12:41] is functionality. [12:43] So, [12:44] You have to make sure the thing like literally works first. [12:49] And so that's really like built into the spirit of how we do product development here. We really bias towards getting something in our own hands to start using it as quickly as possible. [12:59] And that means, like, we can't be debating in Pixels and Figma, which I know seemed, like, pretty archaic, given everyone's clodding everything.

Everyone has, like, their fleet of clod interns. We really, like, want to, I think, most often, like, bias towards building something so that we can just... [13:14] make sure it works, get a feel for, you know, the shape of things and how we want to scope the work. And then we need to make sure that it's reliable. You know, we're a financial services product and company. It's incredibly important that customers deeply trust and can rely on Wealthsimple when it comes to their money. And so reliability is incredibly important to us.

And so, like, those are the foundations that we need to get right. [13:36] The third layer being performance. So like we need to make sure that it's incredibly like fast and frictionless to use the product. [13:43] not lagging, not slow, not crashing. [13:45] And then it's like, how do we make the experience fucking great? But we only really can really dig into those details and make the experience excellent once those foundations are in place. [13:57] And if we do it the other way around, it can sort of be a waste of time.

Not everything is this linear. Like, it's not as if, like, we have checkboxes and, like, but. [14:04] This is just a framework and shared language for people to use on their teams when they are scoping the work together and figuring out what's important right now. [14:11] And I think that has really helped them. And like, it's not always perfect and, you know, far from it. Being able to say like, I don't think we should focus on this implementation detail yet because like, [14:21] We need to make it really reliable. Like that is a helpful tradeoff conversation to have.

[14:25] And before it was just like felt like we were like talking to a brick wall, you know, talking past each other and not actually trying to like work together to. [14:32] to build something really great. Especially in an org that I know you all prioritize, like the craft to place a great emphasis on that. It's really tempting to... [14:41] do those things out of order when it is celebrated. Like I'm assuming there is some level of celebration of craft internally. What makes Wealthsimple such a special place to work and be a designer is that we deeply, deeply care about design and the experience that our customers get.

Our brand, but also our product experience. The reason that we've grown so quickly is because... [15:01] We want our customers to feel like the care that we put into building our product is [15:07] And the attention we we put to the details is the same is the same care you put into managing your money. [15:13] And so like if you open our app and you see a bug and you feel like it's janky, then you're like, I don't trust these people with my money. That framing has like really helped the team, I think, level up and realize that like, oh, these like small UI bugs really do matter because...

[15:27] over time, they're paper cuts and they wear down that trust battery and people won't stay with Wealthsimple or they won't join us in the first place because they hear that our product is like kind of janky. We want you to feel confident and like we have your back. But also like, [15:42] There's moments where you can have fun. [15:43] You know, and like, you don't have to take life that seriously. Like there's moments to celebrate those moments where like, [15:49] I think joy can make such a big difference. [15:52] Like in our in our app on the home screen, you scroll all the way to the bottom.

[15:56] We have a 3D coin that you can spin and it's like a fidget spinner. All you can do is spin this coin and... [16:02] The number of people that are coming to our app to spin this coin, and it's like people talk about it on Reddit all the time. It's like their favorite thing is wild, but it's like a moment of levity. You know, you're like opening the app to check the markets, and they have been really... [16:16] wild lately and then you like scroll down and have this like little moment and fidget spinner.

It's like little moments like this, I think, not to jump ahead too much, like, but this is where design is going to continue to play an outsized role in delivering a really exceptional product. It's like, [16:30] We still need humans to like come up with these like really creative and exciting ideas, like deeply connect to the customer. [16:36] I'm glad that you're entering this conversation from the finance background and you can still add a fidget spinner. Yeah. If you were representing some prosumer tool, it would still be a great idea, but it wouldn't hit as hard as like, no, we literally are building the leading finance company in Canada and we have a fidget spinner and people love it.

So maybe we could talk about that. [16:58] bucket of opportunities. And you talked about the dog fooding, defining quality, really strengthening the foundation. My assumption is that does unlock a lot more space to find ways to elevate this experience and push the craft forward. So what does that look like in practice at What's Simple right now? [17:16] What has been really exciting about these AI tools and like mostly clawfoot, right? [17:22] I feel like it's what everyone's using at this point. I find it's like really helping designers on my team lean into their spite.

[17:28] I've been really enjoying hearing all these different design leaders, a few of which you've had on the podcast, talk about how they hire, what they look for, sort of like the makeup of their teams. A lot of that resonates with me and is sort of how we operate here, too. Maybe another lens on top of that is like this sort of Spike philosophy. [17:44] Where, you know, I believe that as a design leader, you have to really see people and understand what they bring to the team that no one else is going to bring to the team.

[17:53] And we call that a spike. So whenever we interview anybody, like within design or other teams, [17:59] And we're sort of calibrating, you know, should we hire this person? Where would they fit? [18:03] We ask what their spike is. And if you cannot name a spike this person has, then, like, we're not interested. Because every single person that we're recruiting to this team, back to my sports analogies, like, has got to bring something special that's going to help all of us level up. [18:16] And if they don't have that thing, then it's like, [18:18] I don't want to build a team of all the same people who are good at the same thing.

It's like not going to... [18:23] help us deliver the best product experience. My husband's a big baseball fan and the season has begun. You know, you need like a really great pitcher and a great hitter. And like, yes, sometimes very rare occasion, Shohei type baseball players are great at both. Those are like principal designers. But most of the time, like you want to recruit people, I think, who are like really good at hitting or really good at pitching. And then you have to make sure that you can [18:46] be a matchmaker and like find the right role and team for them.

And I think like that's where the magic really happens. I think it's like really dangerous to like identify a spike and then put somebody on a part of the product or a team where they can't actually lean into that thing. Not all teams are equal. Not all teams are working on the same stuff. Some are working on former like technical flows or experiences. Some are working on... [19:07] you know, like a growth team where it is like a lot more like brand focused, a lot of fun, a lot of quick experiments.

And so like you wouldn't want to put someone who's like, [19:16] really gets joy and energy from working on, like, deep technical problems, like, on a growth team to do growth experiments. Because they'd be like, I don't, this is, like, not my thing. And vice versa. And so there's, like, this matchmaking exercise that happens and is continuously happening within the team internally. [19:31] So I think it's like super, super important to like getting the most out of everybody. [19:36] And what's cool to come back to these AI tools is like, [19:39] What I'm seeing on my own team is that [19:42] People are using the tool to amplify their spike.

[19:45] And to like really go deep on the thing you're already really great at. [19:49] And so... [19:50] you know, naturally, like for the folks on my team who are more like design engineering profile, [19:55] They were already like fairly technical... [19:57] And maybe they were like, [19:59] an iOS developer before, or they just like are really comfortable building like React apps or something. They're biasing towards like prototyping really quickly and just sort of like leading into that. And they can build prototypes that maybe we could actually ship. Like the quality of them is quite good because they know how to like, [20:14] sort of, I think, like, review the code and make sure the quality is high enough, you know, versus folks who are, like, not as technical.

And that's, like, a big ask and leap for them, I think. Obviously, Claude can help, but, like, [20:23] Still, we're seeing this challenge of like product and design fluffing our poor engineers with PRs. And they're like, we don't have time to review them all and like have them are garbage. You know, this is another topic we can get to. But anyway, so like the more technical people being able to do even more. And then like the folks who are like more of the visionaries who are like really leaning into like the beginning of the design process, still using these prototyping tools to like visualize a lot of their ideas super early or to just like talk to Claude,

[20:53] better brief and things like that. So it's like really cool to see like the different points in the process in which people are using the tools. I don't know the answer. [21:01] Everyone on Twitter is trying to tell me what design is now or isn't and whatever. I think [21:07] I know other people have said this too, and I really agree, is like, [21:10] Everyone just has to be really curious and be digging in and trying stuff and seeing what works for them. But I'm, you know, we're not trying to be prescriptive about what tools you should be using when.

But I get really excited when people... [21:22] can use it to their advantage and like really show that like secret sauce they bring to their team or their project or whatever. And that's where like I can see them naturally wanting to use the tools and being really excited about them. [21:33] I want to put a pin into the PR process thing because I do want to touch on that for a second. But first... [21:39] Let's dig into the spike piece a little bit deeper, because something that I hear a lot is, you know, it's all about how.

[21:47] Claude, for instance, can enhance somebody who has a little bit of technical curiosity. And it's this progression from designers moving into code where it feels like that is kind of the dominant spike is like, how technical do you feel comfortable being? How much of your statement around spikiness is represented by that part or that quadrant or whatever? [22:07] And maybe do you have other examples for people who are listening? We're like, that's not my spike. Like, I didn't code before all of this happened. And like, yeah, I'm curious, but it's like, that's not my spike.

I have other different types of spikes. Do you see anything else or any other types of examples where you could point out and be like, yeah, that's what it looks like to lean into this moment with AI if you are not somebody who gravitates toward AI? [22:28] owning a bunch of the front end. I think you're sort of this combination of like, [22:32] You can lean into your existing spike or you can discover a new one. There's a designer on my team who leads our options trading experience. [22:40] And she's an options trader herself.

She's an incredible designer, I think, because she just so she so deeply understands the product and the customer. She can really lead that space. But I think she would tell you she's like. [22:51] My spike is not like I'm the best visual designer and the most creative. I'm never going to come up with like the most creative. Wow. Solution or whatever. [22:59] But I'm going to create a really great options trading experience. [23:02] And she had [23:04] a little bit more interest in the technical side of things. [23:07] But now she was just walking us through...

[23:09] The fact that she's basically building the entire front end on her own. [23:12] And like actually reviewing the code and making sure it's of high quality and through the process, like learning so much from that, which I know a lot of people are doing. [23:20] And now I'm like, okay, like she has a new spike, like she has a new skill that she is learning. That's really exciting. And it's sort of interesting to think about like, is that how we want designers spending their time right now? Like, [23:30] understanding code quality and spending all the time like fixing it and reviewing it so that it is production ready.

I don't I don't know. I kind of wish an engineer was just sitting with you and doing that, you know, whereas on the other end of things like designers who would identify their spike as being like very creative, very visual, wanting to spend a lot more time on crafting those details like the last mile. [23:51] They're like using AI to do very different things, like help me generate 3D assets, help me help me like prototype all these like nuanced little details. But it doesn't have to be production ready. It's just helping me like go broad and explore like another designer on my team who's building spend tracking features.

You know, we're working through this like data viz problem and historically, I. [24:13] he would feel like he has to design like one or three options in Figma and take all the time to like, you know, fiddle with the details and then like share it back to the team, be like, which data is his best? [24:23] And like with Claude, he's like building a dashboard of every possible database they could use and using mock data and then feeding in his real data. And he's able to like visualize and make decisions faster.

And so I don't know. Yeah, I think like. [24:35] Regardless of your spike, you can absolutely be using these tools. I don't think it's just for people who like are trying to build high quality front end or ship high quality front end code to production. What's really exciting within the team right now is you're trying to figure out the right team structure. [24:49] And both like size and like who is... [24:52] like the composition who's on this team, given the new tools and how the roles and the lines are blurring.

Like, I think that's really exciting. You know, we used to talk about like two pizza teams. [25:00] Like the size of your team, which doesn't even make sense. It's like we would have teams of like eight to 11. I'm like, they need more than two pizzas. Yeah, y'all haven't eaten as much in Canada. People are hungry. [25:10] It's like four pizza teams. But, you know, that was like the standard. And now we're talking about what it means to have a team of three. And maybe it's a design... [25:18] designer and two engineers maybe it's a designer and a product person engineer like I don't even know what the makeup of those like who are those three people [25:26] But I think it's really interesting to think about how we can have smaller teams who could sit together together.

[25:32] who can move faster with more conviction, who can really share the roles and responsibilities. [25:38] And... [25:39] and like, you know, deliver something they're really proud of. And it kind of comes back to this idea. This is like the reflection I was having is like, [25:45] I feel like the reason I've been able to grow and succeed here is the relationship I built with private engineering and how much I've been able to like learn about their craft and what they care about and how they do their work and how like the three of us can build a really great experience.

[25:58] And so we're just like now at a place where maybe that is just the structure of every team and we have more teams with smaller teams. Like, I don't know the answer yet, but it's like really exciting to think about that and what that would look like. And maybe like the other end of the spectrum might be that everyone becomes like a full stack person who does product and design and engineering. [26:18] That one makes me nervous a little bit because it's important that we have a leader on a team that has conviction and is like driving the work forward that like a team will always make everything better.

Like working with other people to challenge your assumptions or your way of thinking to contribute to those ideas like you just need that. And like I guess some people are saying that like Claude is that team now. Like I think you need humans. [26:39] Still, to do that work, I have seen people ask Claude to do the thinking for them. And it's like garbage in, garbage out. You still got to do all the thinking. [26:48] and the strategizing. And that's also been a really interesting reflection even having is like, [26:53] Speed has always been our advantage at Wealthsimple.

And we always bias to like moving super quickly and, [27:00] But it's, [27:01] With these AI tools, it's like people are skipping the thinking and skipping the design altogether, which is kind of dangerous. You have to go slow to go fast. That's still true. You have to spend time in the beginning thinking about what you want to build, [27:14] having conviction in that, you know, like developing a strong point of view, [27:18] making sure you have conviction and then like spending all of your time, of course, like writing the prompt or the empty file or whatever it is.

[27:24] But you can't just ask Claude to come up with your product strategy for you and then go ship it or whatever. Which is kind of what you see sometimes. Someone on my team uses the phrase slop drop. [27:33] Where like... [27:34] somebody like asks Claude to write a PRD for them and they just like send it to you and you're like, I know you did not think about anything here, you know? I've been thinking about that a lot myself too, because I'm spending way more time in code. Like I basically am always using Claude as the [27:52] when I need to explore things.

Even going back to your original point, like with the spikiness, for instance, quickly. [27:57] tangent is like, I'm bad at graphic design. I won't even say that it's not a spike. Like I'm actually bad at it. It's not who I am as a designer. Like I'm a little bit more like product focused, technical. So all of a sudden the coding world for me is kind of almost just turned me into a, you know, product minded front end engineer in some ways. But when it comes to making a website and, you know, little graphics, actually I was texting Tiago and be like, dude, what do I do here?

I'm like, that's not, that's not me. That's not, [28:24] I don't know how to make a graphic to represent an idea that isn't, you know, in my nice little CSX box. So I'll then have Claude with absolutely no thought whatsoever up front, just be like, can you just dump a bunch of ideas? [28:37] And then I'll look at them like, oh, 4B is interesting. Let's do five more like that. And I don't touch a single pixel and I'll get like a graphic design that I want. And it helps me as somebody who was maybe previously a 3 out of 10 get to like a 6 or a 7 out of 10, which is great.

[28:52] From the product standpoint, though, for myself and probably a lot of people listening, we are kind of still figuring out what is the deep thinking process? [28:59] part of the process up front because so much of, [29:02] the deep thinking traditionally happened because it took time and there was friction to do things and, [29:08] You had to go through all of the steps and your brain is naturally processing through that where now it's like, [29:13] I have a feature idea. [29:14] and I can spit that thing out and send an engineer [29:18] a very sloppy PR in like 90 minutes.

And how do we preserve what makes designers really good critical thinkers in that process? I don't know. It's not even a question. I definitely don't have [29:33] at least for myself, I'm really playing with right now. When everybody can build anything, [29:39] it becomes super clear who has great judgment and who doesn't. And that's why I think everyone has sort of, [29:45] started to talk about this idea of like judgment and taste and, [29:49] being everyone's spike, I guess, and like skillset that they need to lean into and make sure you just like, yeah, really use your strong judgment and intuition, which has always been a big part of how we build product here.

We think speed is incredibly important. And [30:02] a lot of building product is just intuition and judgment and like, [30:06] Taking bets and getting... [30:08] your product at the hands of customers quickly to see how they react and the feedback they give you. We need to like find more people at WellSimple. I think we have created a team and a culture where like that judgment is really strong. [30:18] But a lot of that is also like about culture and how you help people understand the business and the customer and what's really important and understand the shared definition of quality so that if they do want to go run and build something on their own, they like know what the boundaries are and what the bar is.

Sort of interesting. There's one question that I can't stop asking myself. What if companies apply to talk to you rather than the other way around? And that question is the foundation for the all new Dive Talent Network. And it's working. [30:48] Right now, I'm helping many of the most exciting startups that I know to hire the designers and builders who listen to this show. So if you're curious what might be out there and maybe you want to get on my list or maybe you're even looking for your next design hire, head to

club slash talent to join today. Let's talk about craft for a second. We've touched on it. [31:18] at Wealthsimple and is looking for ways to reverse engineer it in their own org or in their own individual practice. I guess I'm kind of curious, like when you think about what has led to [31:28] your ability to consistently crank out really well-crafted product experiences, how much of it is [31:33] just hiring the right people and trusting them to do it. [31:36] versus more intentional ways of working, processes, quality checks, like anything else you all are doing in business.

[31:43] the practice of design at Wealthsimple in order to consistently hit that bar. I would say it's a combination of a few of those things. The most important one being you've got to hire really talented people and trust them to do a great job, get out of their way. [31:57] and let them [31:58] run, you know, and that's the experience I've had with Tiago. [32:02] like Tiago joined our team with, say, at the end of last year, we've seen such a big jump in the quality of our product experience because we found a great leader who can help [32:13] I think, execute on that vision that he has, but also, like, [32:16] work with our team to coach other people and get them there.

And I think it's really important that you build a team where you have those like really exceptional craft leaders who can help [32:26] bring everybody else. [32:28] along and raise the bar for everybody. [32:30] That has been the biggest unlock for me personally and what I've seen on our team. [32:34] You have to make those big investments in people. [32:36] I think also like when you bring on that talent, it's sort of like infectious. The way they show up, the stuff they care about, the things they're sharing is inspiration. It's like created this culture that feels like there's a lot of energy behind it and everybody is sharing what they're inspired by.

I think back to... [32:53] a few years ago and it felt like we were missing that magic within the design team like people weren't [32:59] inspired. They weren't sharing things with one another. They weren't talking to one another and like [33:03] really like celebrating one another's work. And I think you just like over time have to really build that culture and, you know, [33:10] It's not one person. It's all of the leaders really encouraging it, but bringing in the right type of people. I always come back to this [33:18] Again, it's like the sports staff, like you have to put so much [33:21] time and energy into building the right team and making sure that you have great chemistry and that you have a sort of like diverse skill set and experience levels too.

And it's an art and a science, I think. But I feel really proud of the team we've built, but it's taken us years to get here, right? Like it's not, you can't do it overnight. You know, when you see it and you feel it and you see, you know, the results in the product. Having said that, you know, there's more than Tiago on my team. There's so many talented designers. Like I want every person on the team [33:52] And so we have a number of different designers again who are like really great at different things.

So what's interesting with Tiango, this analogy was shared by another principal on the team that we all laughed at and loved. [34:02] is like Tiago's spike is absolutely like the finishing touch, the magic. [34:08] that he adds to every single experience. It's like you just know when Tiago has worked on it. The analogy that [34:14] a team member used is like when you're in a kitchen and working on the line, the person who is plating the food with the tweezers, [34:21] And adding, like, the final flower petal or whatever to make sure it looks exceptional before it goes out.

Like, that is Tiago, you know? Like, that is what he is so, so great at. And so... [34:31] How do we set Tiago up for success where like he can really focus on doing that work and he doesn't have to worry about maybe other stuff that other designers would work on or whatever. Like that's another example of like how do we play to the spike? And yeah, he's just so exceptional at that part of the craft. And then we have another principal, Justin, who is like the visionary. And so if you come to him and you're like, I want to build something that's like early days, something ambitious you want to build.

You don't know what the experience should be. And you go to Justin and you're like, let's get the team excited. Show, not tell. [35:01] some ideas for what this would be. And like, [35:03] 24 hours later, he's going to like blow you away with all these ideas and share them with you. Those are very different strengths. [35:09] And so to come back to your original question, too, of like, how do you think about building a team and really like fostering, I think, a culture of like creativity and wanting everyone to be an A player and like do their best work.

It's also realizing that like not everyone has to be a generalist. And like the way you organize your team doesn't have to be every designers embedded on a product team and they work on their thing and like they have to do it all. Like it's sort of how we operated for a long time. [35:34] But I think having a player coach model, not just with like you and your manager, but like you and other ICs on the team. Can one designer work on a project and then Tiago comes in at the end to really help them like make the details really excellent before we ship it?

[35:48] and like finesse, you know, and add like really exciting motion and have fun with a couple of the details like that sort of model, too, can work. I think there's like no one right way of doing it. But I try and give my team freedom to try stuff like whatever is going to work for you and your team. Like you can you can experiment and see what model is going to be the most successful. And again, especially with these new like AI tools and ways of working like. [36:11] All that's thrown out the window, you know, like Tiago works on a team with two engineers and no product person because they don't need one.

Why not? Why would we add a product person like we don't? [36:20] We don't need you on the team. That's okay. But you want a different project where you'd be more helpful. Not every team has to have the same composition of people and skill sets, which I think has been a big unlock for me and how I think about designing the org. It's probably inspirational for people listening, too, because... [36:35] A sentiment that has popped up multiple times on this show is... [36:38] you know, power to the generalist kind of thing, especially in the AI area.

We want generalist, we want generalist. Like, [36:43] Actually, your take on we want people that really, really spy from one thing. I do think it's maybe a minority take in a way that is refreshing. Okay. And... [36:51] I like having it because... [36:53] Sometimes I almost feel bad for people who are earlier in their career. It's like, well, we want generalists who can own everything end to end. And oh, yeah, you need to be able to code and do products. And like, we're all going to wear all of the hats and you have to be able to wear all of them to get your next job.

My opinion of this is always sort of evolving and changing. But it sort of feels like when you're coming up in your career as a designer, you have to start as a generalist. It's like people used to say to me, like, you should go work at a bunch of different companies, different agencies or different product companies to like understand what you like. [37:20] Like the same... [37:20] the same idea like you should start as a generalist so you can identify the spike like what is the thing you're going to bring to the team that nobody else can bring that you're so exceptional at [37:30] that like you get energy from and can really lean into.

And like, I really believe everyone has a spike, you know, you just might have to like discover what it is. And maybe it changes over time too. Maybe you got like two spikes. I don't know. Like, I think you said you're like a product minded engineer or whatever. Like that's a spike. Part of it is like admitting what you're not good at. [37:46] Admit the saying that you're like, [37:48] I'm never going to be the best, as you said, graphic designer, but I'm really good at product strategy. And I'm like really excited about digging into marketing.

[37:57] front end or really like code now and being able to build stuff on my own. That is what sets people apart in my mind to where I've seen people really succeed. [38:04] Obviously, nothing is black and white and super simple. So I would imagine there's probably this situation where maybe you as the hiring manager [38:12] are trying to make sense of who to bring on where somebody has... [38:17] a really interesting spike in set of skills, but... [38:21] limited domain expertise. [38:24] Whereas you might have another person on the flip side that is like that options trader.

It's like, I know this stuff. I have so many thoughts. I've made all the mistakes already for years. [38:34] How do you reconcile those two types of designers when you're trying to decide who to bring on the team? That's such a good question. And we talk about this constantly. I think we've learned over time where we need the subject matter expertise and where that outweighs the. [38:48] Like the craft stuff. [38:49] sort of thing. So actually, options is a good example. Like we learned... [38:53] Over time, we had a couple other people working on it.

We're like, we need an options trader building this experience. That's how we're going to move quickly and how we're going to build something really great. [39:01] It's a really tough space to sort of like on onboard onto if you're not an active trader. [39:06] And [39:07] You don't like immediately sort of get it. Then there's so many other parts of the product where I actually think you don't have to join the team. Like actually crypto. Like we are hiring folks to work on the crypto product and just from experience. And like, I don't actually think a designer has to like be a DJing crypto trader or whatever to go build a great crypto experience.

It's just what I've seen and observed. [39:30] And so I think we're really thoughtful about like weighing those sort of pros and cons, identifying what we need at that time for that team. [39:37] But there's absolutely no one right answer to that question. It's just definitely based on [39:43] the product, [39:44] the existing team, who are the players on that team already? And what do you feel like is missing and that you need? But, you know, it's like, this is very simple, but sometimes I've seen some leaders on my team build their team and have players that are all good at the same stuff.

So it's like, [39:57] You hire a team of five designers and they're all like really good, like systems thinkers and are like very technical. But like as a result, the UX design is very boring. [40:08] And because like they're just not like those visual designers who are going to like think creatively and about like, you know, I don't know. They just like are missing the creativity sometimes and that extra fallish. [40:17] And so immediately I can say, like, you're missing this skill set on your team. And so you need to think about how you're going to balance it.

It's just like constant conversation and back and forth and. [40:25] We're always hiring and teams are changing and whatever. I'm a believer in small teams. Like, I want to keep my team as small as possible. And that's because... [40:34] I just have seen that smaller teams are more effective. Having said that, my design team is now like 35 people, which feels massive to me. And so coming back to this idea that we want the app to feel like it was designed by one hand, I think it is super important that [40:48] people are aware of what's going on and like communication just becomes increasingly important.

So, you know, in order to like move quickly and not slow down by bureaucracy or other teams or needing to get buy in or needing to share everything like, [41:02] You just have to proactively communicate really well. And so we have a couple rituals in place within the team, within the design team. [41:09] where people are just regularly sharing what they're working on. So like every other week, a domain, we have four domains within the org. Banking is one domain, for example. [41:18] They will come and as a team present the latest work to the rest of the design leadership group, which is principal engineers and directors.

[41:26] And, [41:26] It's, [41:27] purely for visibility and to like talk about the stuff they're working on. [41:32] because... [41:33] We're in such close quarters. We're all designing like the same house. You know, we're all just like sometimes in different rooms. [41:39] And I don't want it to feel like we're all confined to our own rooms and designing in those rooms. And then like everyone comes out and they're like, oh, God, we have different aesthetics in all these rooms, like all these are interior designers, you know, like we have to make sure we're like seeing the opportunities to connect the ecosystem, make the experience better.

Sometimes you're working on sort of like the same things, but different. And just like having that visibility, I think, has really, really helped. [42:01] And I'm sure people would be thinking, like, can you do that async? Like, why do you have to get together and talk about it in person? It's like, because you still have to talk about stuff. [42:08] But like, yes, we can do this all on Slack, but I'm a big believer that like you still got to get in a room and talk things through with one another and have a conversation.

And so every other week, each domain comes and presents that work. And it's an opportunity for all the other leaders to. [42:22] be in the know of like what people are doing and, [42:24] you know, often we'll talk about the craft and we'll talk about patterns that are emerging and like, oh, what do we want to do about X, Y, Z? Or like, oh, I love what you're doing here. I'm [42:33] cross-pollination is so important. And then also like, [42:36] Every designer like knows every other leader on the team too.

[42:39] Like, I just generally feel like my design team... [42:42] Though 35 people now, like we all really know each other. And I think that is so, so important, especially because we're remote. We also get people together in person because I think the only way to like really feel like you're part of a team. [42:54] and be productive. It's like really know people and spend time with them. Like sometimes I have on sites and people are like, what's the point of the onset? I'm like to just spend time together. Don't overthink it.

Like, [43:04] Get in a room together for a couple of days and just like build together and get to know another talk and share ideas and. [43:10] It's always productive. It is never not productive. There's like an anticipation around it too. Like I've only worked remote for a very long time now. And so... [43:18] I typically will be on a team where maybe you have like a quarterly offsite or in a past role we had like twice a year, we have the entire company and then oscillating quarters. We would have just a product team, for instance.

And like kind of everybody gets hyped. You know, you're like you want to bring your best. You want to like tap into the creativity and you. [43:37] I feel like the expectations are always higher for like what we're going to [43:40] accomplish or think about or the conversations that we're going to have in those weeks. And so a lot of my favorite design ideas that I've had have come from off sites. [43:49] Just because the vibe is different, you know, you're just you're coming into it from a different posture. Yeah.

And like going back to this point I made earlier about the thing that helped me grow. [43:58] the most and really quickly was building a relationship with my product and engineering peers. Like my boss, Brett, a few years ago, he started hosting these onsites where he would bring the entire sort of like product leadership team together. [44:10] together [44:11] And we would have these onsites together and we would go to dinner together. And like over the years... [44:16] All of the important conversations are happening at dinner. We've covered a lot of ground, but I want to make sure that we're getting everything here because over the last few years, you honestly have kind of been forming your design leadership philosophy from scratch, right?

So if we imagine it almost as a book that you are depositing little insights or learnings into, are there chapters that we haven't talked about yet that you think are indicative of who you are as a design leader and some of the things that you've learned on this ascent? [44:45] One thing that I do keep coming back to that Brett has instilled in me is you have to hire people that you would want to work for. [44:52] When I like think deeply about the people on my team, I actually want to think about like what I want to report to this person.

You should be able to hire really strong talent and feel like you can trust them to go do the work and do it really well. And we don't have that trust. It's because you like don't have the confidence and they're just like not strong enough. And so... [45:09] It is all about like building this really strong team underneath, I think, to be successful. That was a big unlock for me that took longer than I wanted it to. [45:18] But it's also like it's something I see every day. I think like reflecting on that is really important.

What are the signals that you would look for even in like a portfolio presentation or a conversation with a candidate that would get you to the point where. [45:31] you would have that level of conviction where you would want to actually make them an offer. Maybe we can even reflect on the last few designers you've hired. What were the specific [45:39] points in time where you're like, yep, you're a yes now. Hiring is really challenging. And we're sort of constantly adapting our hiring process to make sure we can get the right signals when we're interviewing people.

So, you know, we have a portfolio interview, which every company does. [45:53] And you show up, you do a button-up presentation, you got a script, you're like ready to go and feel reversed, and you can share the work. [46:00] But what we have found over time is that it's, [46:04] Really helpful to get people off script and see how they react and how they think on their feet. [46:09] And that's going to give you a much more accurate idea of like, what is it like to actually work with this person day to day?

And so we introduced a new interview that's an app review where we ask you to. [46:21] open an app on your phone. We don't tell you what it is ahead of time and do like a live crit of the app. [46:25] Fun. We've been choosing Spotify. I can say that now because I think we're going to change it. This interview has been so incredibly helpful because it has gone... [46:33] Like in every direction you can imagine, like we were we had a point where we were like, what is success for this interview?

And like took us a while to figure out what we were even looking for because every person treats it so differently. It's so open ended. [46:45] But I think the most successful versions of that interview have been people who are like diving in and are so enthusiastic and like have so many ideas and are really opinionated and they can sort of like. [46:58] go high level and then go into the weeds and sort of comment on those. And they're talking about the things they love and the things they don't love.

[47:04] And it's it's tough. Like I it's an intimidating interview and some people I think get like flustered and stuck and I totally relate to that. But the most successful versions of it have been people who are like taking a beat to be like, OK, I want to like do a tour on this app. I want to talk about all the things that I'm like reacting to and seeing and like what's resonating with me. And I think just like really getting a feel for like how people think has been really helpful to us.

Ultimately, like we want people with like really strong opinions. [47:29] I don't want anyone on my team who doesn't have a strong opinion, who can gain conviction and idea and like move it forward. Like everyone is a leader and that's like a leadership quality. We look for it in everybody, regardless of what level you're at or what role you're in. The other thing I love. [47:42] that people do in the interview process and that I find is always a positive signal. [47:46] is when you're having a conversation with them, whether it's like a hiring manager interview, [47:51] Or even in the middle of a portfolio review, some people have done this.

When somebody asks a question and they want to go deeper on a project, [47:58] We've seen people say like, [48:00] I'll just open the Figma and show you. They like open their Figma and they're just like walking around and they're Figma or not walking around, but you know, they're like showing you the Figma file and digging into stuff. [48:09] There's something about the like rawness of that, you know, it's like not scripted. And they're just like, let me just show you like what my work actually looks like. [48:16] And all the different things that I sort of explored or whatever that like gets us closer to what it would actually be like to work with you.

And I love when those moments happen. [48:25] Because, yeah, I just want to get to know the person, too, in the process. Is the deck still the right launching point? Like, if somebody came up. [48:31] If somebody started the conversation and they just open up the Figma, still positive or now is it messy? Yeah, yeah. Okay, that's my thought. Just making sure. I think presentations are absolutely required because we want you to have structure to how you walk through the work. Storytelling is so important and making sure, you know, succinctly like walk us through your journey and what you've been working on.

But there's just these like off the cuff moments that I appreciate. Like I appreciate honesty and just getting a feel for like what does it look like? [49:01] look like. I'm not like, you know, over indexing on that, but it does feel like it's consistently a good signal, I find. [49:08] I had a hiring manager that I worked with and that was his entire approach was basically to get someone, like you said, off script and then have them be able to talk effectively at, [49:17] minute details behind the decision. Like you had to have part of the evaluation happen at the microscopic level.

[49:24] And it was with that pairing of storytelling that those are the two ends of the spectrum that he was evaluating. [49:29] So I get the microscopic level. [49:31] Maybe really quickly, can we touch on the storytelling piece and just imagine that somebody is listening and they have a portfolio presentation tomorrow? [49:39] And they're looking for little tactics or something that maybe you've seen as a hiring manager. It's like, wow, that was good. That actually stood out from the sea of portfolio presentations that I'm sitting in front of. I think what makes portfolio reviews and presentations so challenging is,

[49:56] is finding the right [49:58] altitude to present the work at and like [50:00] balancing the like, how do I tell the bigger picture or how do I give them a sense of the bigger picture, but also show them the details. [50:07] And I find often folks miss out on showing the details, but [50:11] When we're assessing your craft, like, that's what we're assessing. And so... [50:16] I actually find that a lot of folks are really great at the storytelling part. Like, [50:20] here's my journey at this company. Here's the problems we've been solving.

Here are the steps in my process. Here's the results. Here's what we learned and how it performed, whatever. But that's why I get excited about people pulling up Figma because it's like, I want you to show me, can you like share your phone screen with us and walk through like the thing you shipped in fraud and like talk about what you love about it, what you don't love about it. You know, so often what we design in Figma is not actually what makes it a production. Like talk about that and that sort [50:50] this like moment and why you spend so much time on it.

A lot of people actually like show static stigma stuff in their presentation, which I feel like is unacceptable at this stage run. [51:00] It's like, we got to see prototypes. You want it. I want to see how this feels. [51:04] how you made trade-offs and decisions. It's funny to me, actually, that nobody... [51:08] or I haven't seen anybody actually like open the products they've been working on in production and talk about like the thing that they designed and built. [51:17] Kind of strange, eh? I don't know if I've ever seen that either.

Yeah, but it's like, why not? Like, this is the thing you literally signed and built with your team. There's no better flex than showing something and clicking through it, and it's good. Like, this is a live demo of the thing that I built. I think that would be huge. You know, we don't have infinite amount of time in these reviews, but