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- [00:00]
A
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, a while simple. It'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.
- [00:21]
B
Welcome to Dive Club. My name is Rid, and this is where designers never stop learning. Today's episode is with Polly Darcy, who, over a few short years, went from an IC at Wealthsimple all the way to head of Design and eventually VP of Design. So we're gonna 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.
- [00:49]
A
I joined Wellsimple 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're only five, so we were a super small team. We were still like a sort of a centralized team within the company, 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 showed up to work and you were working on a different part of the product because the product was 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 a team, and that's sort of like, where I get most of my energy and what I really enjoy doing. And so I moved into this manager role, and I was managing, I think, like three people, and I was just sort of learning the ropes, but super green, super new to management, and, you know, still had no idea what I was 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 incredible opportunity. He was like, you know, I. I really see something in you, and I think that you should lead this design team. I was like, what? Are you sure? 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 gonna start. Looking back, I think something I really admire about Brett and what he's taught me is, like, when you see potential in people on your team, you need to give them opportunities and support them and help them grow. Every time you give somebody an opportunity, it's a bet, like, 50% of the time those bets are going to play out and work really well, and 50% of the time, they might not. 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, you know, I also want to give them an opportunity to grow and take on something new and challenging. And that's what Brett gave me and. And sort of, like, started my trajectory here. 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, and it just, like, hit me in that moment as I was going through this sort of challenging time of figuring out, like, my new role of 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 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 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. And so it's something I tell 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 was not very good. You know, we were growing, but the quality of our product was, was nowhere where it needed to be. Like, you would open the app and there would be bugs and it was really janky 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 if you, as someone who is a sort of maker and owner at the company building this product, do not want to use it with your own money, it's not good enough. You either have to like come to us and tell us why it's not good enough and, but also you have to bias towards action and like take the steps to make it really great. And you know, like, if you're not going to use it, why anybody else? And so that's when this like first sort of era began. And the first big shift we had to make in the culture was all around dogfooding and getting everybody who is building or selling the product. Because at Wealth Symbol 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. 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 you like putting their own money in the app. The beauty of our product is like you can open any account, it's free, you can put in a dollar, you can put a 10 bucks. And I just wanted people to like explore the product, use it, open every new account, test every new feature so they really understood what our customers were experiencing and then share your feedback and like push through what you think should be better. Because you know, it's one thing to like test something in staging and it's another thing to actually like use a product with your own money because you just, you like are 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 sort of philosophy and culture where like every new hire I host an onboarding session with them where I like do a live walkthrough and tour of our app and then we talk about how you dog food. And as a result, 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 just feedback about how to make something better or a feature that was missing or something that didn't make sense.
- [06:28]
B
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, totally reshaping the way that I think about my design process. And in the time that it would take me to make two manual iterations, I can see a design 10, 20 different ways on the canvas, and I 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 and 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 is truly taken my design process to the next level. I cannot recommend it enough. Just head to Dive Club Slash Paper to start designing today. All right, Framer just released two killer AI features that I have to tell you about. The first is Wireframer. You can chat with AI to skip the blank canvas and spark all kinds of ideas. There's no easier way to spin up a responsive page with structure and starter content that's ready to edit. The second feature is Workshop. It's a way to create advanced components using natural language so you can spin up all types of new visual effects, no coding required. It's just another reason why I recommend Framer to absolutely everyone. And you can start using these features today. Just head to Dive Club 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. It's like, there's a reason there's a lot of, like, design and dev tool teams that are so well crafted. It's because, like, yeah, you have to use the product every day. So instilling that in the culture, it makes total sense. I'm kind of curious, like, were there other opportunities that you saw in the very beginning or even just ways that, you know, 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.
- [08:52]
A
I think the most challenging part of my career so far has been that, like, step I had to take from being a manager of like three people to leading a design team and then, you know, being responsible for executing and really like, shifting the culture to make sure we were building the most talented team in the world and also like, delivering a product that was really exceptional. And I think the only way I got through that period of feeling some like, self doubt or uncertainty about what to do was 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. But the thing that has helped me grow the fastest and the most is sort of like, had a come to Jesus moment about who my first team was. Like, 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 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. And those are the people who I'm the closest with now and who really helped me because they were able to just sit me down and be like, you're not seeing 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 and making decisions together and we butt heads all the time. But I think having those people to give you feedback, to bounce ideas off of is so incredibly important. It, like, comes back to this idea of a team. We have different types of teams and different altitudes. It will simple, like, I want it to feel like every designer who joins my team is part of a design team and you have sort of like a culture and a relationship with those people. Because ultimately the goal is that I want the app to feel like it was designed by one hand and not 40. That is incredibly hard to do. It's kind of impossible. But that's the goal. And so in order to do that, like those 40 people gotta 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 how you ship the org chart. And so I think I've heard about other companies where like 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]
B
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 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 processes or practices or anything else that you feel like you really intentionally instilled in the day to day, week to week practice ofdesign@willsimple to achieve that goal?
- [11:53]
A
Everybody was sharing all this feedback and then we had no 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? And that's when we had to start defining quality and what it meant for us and at will. Simple like what the bar was. 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 knew like what to tackle first and where to start. And then like that shared language sort of permeates throughout the organization and now people are, you can just like more easily align on what's important to fix first and sort of like where to begin.
- [12:35]
B
Can we get really specific for a second, like what's on this chart?
- [12:38]
A
So at like the bottom of this diagram is functionality. So you have to make sure the thing like literally works first. 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. And that means like we can't be debating in pixels and figma, which already I know seemed like pretty archaic given everyone's clotting everything. Everyone has like their fleet of Claude interns. We really like want to, I think most often like bias towards building something so that we could just 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, the third layer being performance. So like we need to make sure that it's incredibly like fast and frictionless to use the product. Not lagging, not slow, not crashing. 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. And if we do it the other way around, it can sort of be a waste of time. Not everything is as linear. Like it's not as if like we have checkboxes and like, but 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. 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 we need to make it really reliable. Like that is a helpful trade off conversation to have. And before it was just like felt like we were, you know, like talking to a brick wall, you know, talking past each other and not actually trying to like work together to, to build something really great, especially in an org
- [14:35]
B
that I know you all prioritize like the craft to place a great emphasis on that. It's really tempting to do those things out of order when it is celebrated. Like, I'm assuming there is some level of celebration of craft internally.
- [14:48]
A
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 we want our customers to feel like the care that we put into building our product and the attention we we put to the details is the same, is the same care we put into managing your money. 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 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, there's moments where you can have fun, you know, and, like, you don't have to take life that seriously. Like, there's moments to celebrate. There's moments where, like, I think joy can make such a big difference. Like in our. In our app, on the home screen, you scroll all the way to the bottom. We have a 3D coin that you can spin, and it's like a fidget spinner. All you can do is spin this coin. 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 as, like, their favorite thing is wild, but it's like the moment of levity. You know, you're like, opening the app to check the markets, and they have been really wild lately. And then you, like, scroll down and have this, like, little moment in 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, we still need humans to, like, come up with these, like, really creative and exciting ideas, like, deeply connect to the customer.
- [16:37]
B
I'm glad that you're entering this conversation from the, like, finance background. And you can still add a fidget spinner. Yeah, if you were, like, 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 bucket of opportunities. And, you know, you talked about the. The dog feuding, 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 wealth simple right now?
- [17:17]
A
What has been really exciting about these AI tools and, like, mostly clothes, I feel like, is what everyone's Using at this point, I find it's like really helping designers on my team lean into their spite. 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 where, you know, I believe that as a design leader, you have to, like, really see people and, and understand what they bring to the team that no one else is going to bring to the team. And we call that a spike. So whenever we interview anybody, like within design or other teams, and we're sort of calibrating, you know, like, should we hire this person? Where would they fit? We ask what their spike is? And if you cannot name a spike this person has, and 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. And if they don't have that thing, then it's like, I don't, 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 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 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, 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, 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 that I think is like, super, super important to, like, getting the most out of everybody. And what's cool to come back to these AI tools is, like, what I'm seeing on my own team is that people are using the tool to amplify their spike and to, like, really go deep on the thing they're already really great at. And so, you know, naturally, like, for the folks on my team who are more like, design engineering profile, they were already, like, fairly technical and maybe they were like 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, leaning 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, 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 clocking out. But, like, 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, like, visualize a lot of their ideas super early or to just, like, talk to Claude, talk to ChatGPT, to, like, process their thoughts and, like, write a 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 to, you know, everyone, everyone on Twitter is like, trying to tell me what design is now or isn't and whatever. And it's like, I think I know other people have said this too, and I really agree is like, 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 you. What tools you should be using when. But I get really excited when people 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.
- [21:34]
B
I want to put a pin into the PR process thing because I do want to touch on that for a second. But first, 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 Claude, for instance, can enhance somebody that 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? And maybe do you have other examples for people who are listening, who are 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, you know, owning a bunch of the front end, I think
- [22:31]
A
you're sort of this combination of, like, 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, and she's an options trader herself. She's an incredible designer, I think, because she just. So she so deeply understands a product and the customer, she can really lead that space. But I think she would tell you she's like, my spike is not like, I'm the best visual designer and the most. I'm never going to come up with, like, the most creative wow solution or whatever, but I'm going to create a really great options trading experience. And she had a little bit more interest in the technical side of things, but now she was just walking us through the fact that she's basically building the entire front end on her own 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. 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 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 and like the last mile, 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 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 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? 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, 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 we're trying to figure out the right team structure and both like size and like, who is 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, like the size of your team, which doesn't even make sense. It's like we would have teams of like 8 to 11. I'm like, they need more than two pizzas. I think.
- [25:07]
B
Yeah, y' all aren't eating as much in Canada.
- [25:09]
A
People are hungry. Yeah, 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 designer and two engineers. Maybe it's a designer and a product person and engineer. Like, I don't even know what the makeup of those like, who are those three people. But I think it's really interesting to think about how we can have smaller teams who could sit together, who can move faster, with more conviction, who can really share the roles and responsibilities and, 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, I feel like the reason I've been able to grow and succeed here is the relationship I built with product engineering and how much I've been able to learn about their craft and what they care about and how they do their work and how the three of us can build a really great experience. And so we're just now at a place where maybe that is just the structure of every team and we have more teams, but smaller teams. I don't know the answer yet, but it's really exciting to think about that and what that would look like. And maybe the other end of the spectrum might be that everyone becomes like a full stack person who does product and design and engineering. 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 like, 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 human 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 gotta do all the thinking and the strategizing. And that's also been a really interesting reflection you've been having. Is like, speed has always been our advantage at Wealthsimple and we always bias to like moving super quickly. But it's with these AI tools, it's like people are skipping to think and like skipping the design altogether, which is kind of dangerous. You know, you have to go slow to go fast. That's still true. Like, you have to spend time in the beginning thinking 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 then like spending all of your time, of course, like writing the prompt or the MD file or whatever it is. But like, you can't just like ask Claude to come up with your product strategy for you and then like go ship it or whatever, you know, which is like kind of what you see. Sometimes someone on my team uses the phrase slop drop, but where like 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.
- [27:41]
B
You know, I've been thinking about that a lot myself too, because I'm spending way more time in code. Like I, I basically am always using Claude as the dominant interface and then I will use the canvas through Claude when I need to explore things. Even go back to your original point, like with the spikiness for instance. Quick tangent is like, I'm bad at graphic design. I won't even say that. It's, it's not a spike. Like I'm actually bad at it. It's not who I am as a designer. Like I' 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 Thiago and be like, dude, what do I do here? I'm like, that's not, that's not me. That's not. 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? 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 from the product standpoint though for myself and probably a lot of people listening. Like we are kind of still figuring out like what is the deep thinking part of the process up front? Because so much of the deep thinking traditionally happened because it took time and there was friction to do things and you had to go through all of the steps and your brain is naturally processing through that. Where now it's like I have a feature idea and I can spit that thing out and send an engineer 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. I. It's not even a question. I definitely don't have the answer, but I think it's something that at least for myself, I'm, I'm really playing with right now.
- [29:36]
A
When everybody can build anything, it becomes super clear who has great judgment and who doesn't. And that's why I think everyone has sort of started to talk about this idea of like judgment and taste being everyone's spike, I guess and like skill set 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 a lot of building product is just intuition and judgment and like taking bets and getting your product into the hands of customers quickly to see how they react and the feedback they give you. We need to like find more people at Wealthsimple. I think we have created a team and a culture where like that, that judgment is really strong. 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.
- [30:34]
B
There's one question that I can't stop asking myself. What if companies applied to talk to you rather than the other way around? And that question is the foundation for the all new Dive Talent Network. And it's working. Like right now I'm helping many of the most exciting startups that I know to hire the designers and builders who listen to this show. So if you're curious what might be out there and maybe you want to get on my list, or maybe you're even looking for your next design hire head to Dive Club Talent to join today. Let's talk about craft for a second. We've touched on it. I kind of want to go a little bit deeper and maybe speak to the person listening who's very familiar with the bar that you all have set 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 your ability to consistently crank out really well crafted product experiences, how much of it is just hiring the right people and trusting them to do it versus more intentional ways of working processes, quality checks, like anything else you all are doing in the practice of design at Wealthsimple in order to consistently hit
- [31:47]
A
that bar, I would say it's a combination of a few of those things. The most important one being you got to hire really talented people and trust them to do a great job, get out of their way and let them run, you know, and that's the experience I've had with Thiago. Like, Thiago joined our team with Faye 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, I think, execute on that vision that he has, but also, like, 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 bring everybody else along and raise the bar for everybody. That has been the biggest unlock for me personally and what I've seen on our team. You have to make those big investments in people. I think also, like, when you. 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 a few years ago when it felt like we were missing that magic within the design team. Like, people weren't inspired. They weren't sharing things with one another, they weren't talking to one another, and, like, really, like, celebrating one another's work. And I think you just, like, over time, have to really build that culture. And it's not one person, it's all of the leaders really, like, encouraging it, but, like, bringing in the right type of people. Like, I always come back to this. Again, it's like the sports stuff. Like, you have to put so much 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 many 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 result 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 to feel like they're the A player, too. And so we have a number of different designers, again, who are, like, really great at different things. So what's interesting with Tiago this analogy was shared by another principal on the team that we all laughed at and loved. Is like, Thiago's spike is absolutely, like, the finishing touch, the magic that he adds to every single experience. It's like, you just know when Thiago has worked on it. The analogy that 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 and adding, like, the final flower petal or whatever to make sure it looks exceptional before it goes out, like, that is Thiago, you know, like, that is what he is so, so great at. And so how do we set Thiago 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. Like, can we mock up some ideas for what this would be? And, like, 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. 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 designer is 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. 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, 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 all that's thrown out the window, you know, like Tiago works on a team with two engineers and no product person because, like they don't need one. Why not? Why would we add a product person? Like, we don't, we don't need you on the team. That's okay. But would 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, for me and how I think about like designing the Org.
- [36:33]
B
It's probably inspirational for people listening too because a sentiment that has popped up multiple times on this show is, you know, power to the generalist kind of thing, especially in the AI area. We want generalists. We want generalists. Like 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 and I like having it because 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.
- [37:05]
A
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 at different agencies or different product companies to like understand what you like. Like the same, 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 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. Admit the thing that you're like, 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, you know, front end or what I like code now and being able to build stuff on my own. That is what sets people apart in my mind. And where I've seen people really succeed,
- [38:05]
B
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 are trying to make sense of who to bring on, where, you know, somebody has a really interesting spike instead of skills but limited domain expertise. 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. How do you reconcile those two types of designers when you're trying to decide who to bring on the team?
- [38:39]
A
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 like the craft sort of thing. So actually options is a good example. Like we learned 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. It's a really tough space to sort of like on onboard onto. If you're not an active trader and 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, have 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 DJ and crypto trader or whatever to go build a great crypto experience. It's just what I've seen and observed. And so I think we're really thoughtful about like weighing those sort of pros and cons and identifying what we need at that time for that team. But there's absolutely no one like right answer to that question. It's just definitely based on the product. The like the existing team who, who like who are the players in 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 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 UXE design is very boring. 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 polish. 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 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 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 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 slowed down by bureaucracy or other teams or needing to get buy in or needing to share everything, like, you just have to like proactively communicate really well. And so we have like a couple rituals in place within the team, within the design team, 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. They will come and as a team present the latest work to the rest of like the design leadership group, which is principal engineers and directors. And it's purely for visibility and to like talk about the stuff they're working on. Because 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. 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 different 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, the same things, but Different. And just like having that visibility, I think has really, really helped. And I'm sure people are 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, this is love to talk about stuff, like, yes, we could do this all in 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 be in the know of like, what people are doing. And 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 xyz? Or like, oh, I love what you're doing here. I'm going to bring that back to my team. And that like, cross pollination is so important. And then also, like every designer, like, knows every other leader on the team too. Like, I just generally feel like my design team 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 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 onsite? I'm like, to just spend time together. Don't overthink it. Like, get in a room together for a couple days and just like build together and get to know another, talk and like share ideas. And it's always productive. It is never not productive.
- [43:13]
B
There's like an anticipation around it too. Like, I've only worked remote for a very long time now and so I typically will be on a team where maybe you have like a quarterly off site or in a past role. We had like twice here. We have the entire company and then oscillating quarters. We would have just the product team, for instance.
- [43:30]
A
Yeah.
- [43:30]
B
And like kind of everybody gets hyped. You know, you're like, you, you want to bring your best, you, you want to like tap into the creativity. And I feel like the expectations are always higher for like what we're going to 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 just because the vibe's different. You know, you're just. You're coming into it from a different posture.
- [43:54]
A
Yeah. And, like, going back to this point I made earlier about the thing that helped me grow the most and really quickly was building a relationship with my product engineering peers, like my. My boss, Brett. A few years ago, he started hosting these on sites where he would bring the entire sort of, like, product leadership team together, and we would have these on sites together, and we would go to dinner together. And, like, over the years, all of the important conversations are happening at dinner.
- [44:19]
B
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, like, 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?
- [44:46]
A
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. 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 when you 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 it is all about, like, building this really strong team underneath you. I think to be successful, that was a big unlock for me. That took longer than I wanted it to. But it's also, like, it's something I see every day. I think, like, reflecting on that is really important.
- [45:23]
B
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 you would have that level of conviction where you would want to actually make them an offer? Maybe we could even reflect on, you know, the last few designers you've hired. Like, what were the specific points in time where you're like, yep, you're a yes. Now?
- [45:42]
A
Hiring is really challenging, and we are 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, and you show up, you have your button up presentation, you got a script, you're like ready to go and feel rehearsed and you can share the work. But what we have found over time is that it's really helpful to get people off script and see how they react and how they think on their feet. 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 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.
- [46:26]
B
Fun.
- [46:26]
A
We've been choosing Spotify. I can say that now. I think we're going to change it. This interview has been so incredibly helpful because it has gone like in every direction you can imagine. Like we were, we had a point where we were like, what even is success through 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. 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 they're really opinionated and they can sort of like 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. And it's, it's tough. Like I, 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, okay, I want to like do a tour of 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. Like, 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 in everybody, regardless of what level you're at or what role you're in. The other thing I love that people do in the interview process and that I find is always a positive signal is when you're having a conversation with them, whether it's like a hiring Manager interview 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. We've seen people say, like, I'll just open the figma and show you. They like open their figma and they're just like walking around in their figma or not walking around. But, you know, they're like showing you the FIGMA file and digging into stuff. 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 and, 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 because, yeah, I just like, want to get to know the person too in, in the process.
- [48:28]
B
And is the deck still the right launching point? Like if somebody came up, if, if somebody started the conversation and they just open up the figma, still positive or now is it messy?
- [48:37]
A
Yeah.
- [48:38]
B
Okay, that's my thought. Just making, just making sure.
- [48:40]
A
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, what does it look like? A peek behind the curtain, you know, like, what is your FIGMA file actually look like? Not like, you know, over indexing on that, but it does feel like it's consistently a good signal.
- [49:08]
B
I find 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 minute details behind the decision. Like he had to have part of the evaluation happen at the microscopic level. And it was with that pairing of storytelling that like, those are the two ends of the spectrum that he was evaluating. So I get the microscopic level maybe really quickly. Can we touch on the storytelling piece and just imagine that somebody is listening and they have a portfolio presentation tomorrow and they're looking for little tactics or something that maybe you've seen as a hiring manager where it's like, wow, that was good. Like, that actually stood out from the sea of portfolio presentations that I'm sitting in front of.
- [49:52]
A
I think what makes portfolio reviews and presentations so challenging is finding the right Altitude to present the work at and like 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? And I find often folks miss out on showing the details. But when we're assessing your craft, like that's what we're assessing. And so I actually find that a lot of folks are really great at the storytelling part. Like 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, formed or 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 to production. Like talk about that and that sort of process. Dig into the details and talk about how you designed this interaction, this like moment and why you spend so much time on it. A lot of people actually like show static FIGMA stuff in their presentation, which I feel like is unacceptable. This, this, this the stage we're at, it's like we got to see prototypes, we want it. I want to see how this feels and you know, how you made trade offs in decision. It's funny to me actually that nobody 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 design and built. Kind of strange, eh?
- [51:18]
B
I don't know if I've ever seen that either.
- [51:20]
A
Yeah, but it's like, why not like this is the thing you literally designed and built with your team.
- [51:25]
B
There's no better flex than like showing something and clicking through it. And it's good.
- [51:28]
A
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 folks often stop at the like. And then we shipped it and this is how it performed. What happened then? Like did you keep iterating on it and making it better? Like you know, what did you learn five months down the road? Maybe some folks don't have the opportunity to keep working on the same project or whatever, but so much of what we do at Wealthsimple is iterating and keeping like building on an experience. You learn so much over time, and it evolves so much over time. And we love internally talking about the evolution of our products and seeing where they started from and, like, how great they got and how shitty they were at the beginning. You know, I find folks aren't usually talking about that evolution. It's just like a linear, like, and then we shift this thing, and there's a lot of tension that lies in the, like, iteration and. And a lot of learning and, like, fun stuff that comes out of that too. It's not just like, you design something from 0 to 1, you know, and
- [52:23]
B
it's not representative of even how teams are working as much anymore. You know, like, the. The. The giant process at the beginning is kind of fading towards the quick ship, be decisive, and then iterate obsessively.
- [52:33]
A
Yeah, Yeah, I think. I think people feel pressured to come up to, actually. I mean, I see this less now. It's like five years ago, but, you know, people would show up to an interview and be like, here's the double diamond. Like, when has anyone ever follow the double duck? You know, like, be honest with me. Like, how are you actually working? There's something performative about that, and I would rather people just be honest about, like, this is how we work at the place I'm at. It's not necessarily, like, what I believe to be the only way to work, but, like, this is how we're building and shipping and what I'm learning throughout the process. Like, I think some people expect or think there's, like, one way to do design, and they have to show that they know that one way, you know?
- [53:08]
B
Okay, final parting question before I let you go here. And again, I kind of just want to speak to a very specific listener who, I don't know, maybe they did just get a promotion or maybe they got a new role, or maybe they're working on a project that's stretching them and they're feeling a level of imposter syndrome that is slightly foreign and not really sure how to feel about that and what to do with it. You know, listening to your story, I'm sure that there were moments in time where you just felt like, whoa, like, I am in front of my skis right now, and I'm curious if you have any parting thoughts for that listener before I let you go.
- [53:41]
A
I have imposter syndrome every day still, and I think that means that I am constantly challenged and growing and taking on new things. And I think if you don't feel that, then you're probably stuck and you're not doing enough to grow and you need to be more ambitious and challenge yourself. 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, a while symbol, it'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. But also, like, ask for help. Like, I find so many people think they have to solve these problems on their own. And I know that some roles, it can feel isolating, like, maybe you don't know who to go to. But again, like, I have felt leaning on my product and engineering counterparts to ask them for feedback and help has unlocked so much for me. You need to find people who can be real with you and are actually going to tell you, like, what you need to change and do better because that's the only way you know you're going to get better. And that I feel very lucky that I found those people. But you got to seek those people out and build those relationships and then I think it's really rewarding and. And you will do the same for them, too.
- [54:48]
B
Polly, I'm sure this podcast has been super helpful for a lot of people, so really, really appreciate you coming on and sharing a little bit about your experience. Just all of the ups and downs, what you're learning, and then also just adapting to this moment in time. It's been a fantastic conversation and I'm just appreciative that you came on. So thank you.
- [55:04]
A
You, thank you so much. Thanks for having me.