Rid (2:52)

Real quick message and then we can jump back into it. Fun fact for you. I'm right on the cusp of the top 1% of granola users. So when I say I cannot get enough of this product, I mean it.

Interviewer (3:02)

I.

Rid (3:03)

It is that good. But after seeing their end of year crunched report, I have even more respect for this product. I never have a conversation about design without grunting Granola. And somehow it perfectly organizes all of it for me, whether it's chatting with guests for Dive Club or doing user research or keeping track of tasks for In Flight. And then Crunched gave me this beautiful synopsis of all of the key themes and even some funny moments from the past year. It's just a good product. So if somehow you're not already using Granola, head to Dive Club Granola to spin it up for your next meeting. Another week, another huge lovable release. They now have connectors with products like perplexity, 11 labs, firecrawl, and even Miro. So you can build apps that pull live data from anywhere on the web or maybe even talk to you. And it's as simple as writing a prompt like, read this page out loud when users tap play. I mean, connectors totally blow the roof off of what you can create with natural language. And you can start today, just head to Dive Club Lovable to start building.

Interviewer (4:12)

Okay, now onto the episode. What have been the size of the team when you kind of put up these two states in time where you have like the small team, you, a couple other people. Last time I talked to you, I think it was just you fee and like Maybe two other people. Where do some of the biggest deltas exist? Like, can they go one level deeper? What are the biggest changes that you see when you kind of reflect on these two points in time?

Henry Modisette (4:38)

One, we're doing a lot more every day and the second is we have to reconcile with the fact that we're doing a lot more every day. The doing more is, is allowing us to do more specialized things, you know, on our creative studio side of, of the house, where we have people doing like motion design and video production and things that maybe were just moonlighted in the past by one person, there's sort of like a increase in depth of the work and specificity of the work and we've pretty much done everything in house. On, on the brand side of things, it just like it lets us figure out who we are and, and, and evolve it and experiment and go fast. On the product side, there's just a lot of parallelization. I mean, fortunately there's business. Wonderful property of a search product where users show up and they tell you what they want and you just have to show them what they asked for. There's very little collision, you know, from a product perspective between the features. If you've worked on like a feed or something like that, it's all collision all the time. You know, there's a lot of competing goals, competing metrics, UI that needs to balance for the user's side of things. It needs to feel balanced from the internal side of things. It's like 100 teams battling it out, you know, so we don't have that problem, which, which is really nice to be honest. We can ship our org chart in a way that really doesn't cause an issue. It's been fun to see how much we can ship every week and how much is getting worked on and things like that. But, you know, the consequence, all that is like, there's a lot of process stuff that we need to think about, like how do we collaborate and how do we get feedback and how do we ensure consistency and a lot of stuff that was like in people's heads, whether it's the design system or the state of the code or whatever now probably needs to be written down and communicated and how do we do that in like a modern way and not just sort of fall back on like what other companies do.

Interviewer (6:22)

I want to go a lot deeper into what this era of growing up looks like. I think I'm going to put a pin in that for a second and I'd actually like to learn a little bit about this process of going from just you to now 31 people. And maybe before we get into the details and the strategy behind it, can you just give some rapid fire context around who all is included in that group of 31 and how do you think about the org structure?

Henry Modisette (6:45)

We have I would say like 3 sub orgs of the design team. There's, we call it our creative Studio. They're doing like brand design, marketing, like whatever, anything you see that's not the product. In that team they're doing like graphic design, web design, motion design, video production, we're marketing our new features, we're doing brand marketing, we're doing advertising in countries all over the world. So they're quite busy. We also collaborate with celebrities for our some of our marketing stuff. So like you may see something with like Lewis Hamilton or Leon Aldo. The second org, which is the smallest one is our operations sign Ops. That team just kind of keeps, keeps everything running and functional. It's very meta but very important. So that that's how we were able to do all of that creative work and do it on time, do it in a coordinated way. It also lets us run our merch store, Perplexity Supply. So that's run by the Ops team. The third sub org is Product Design. I would kind of cut it between like three different products. One is Perplexity the consumer side, one is Perplexity the enterprise side. And then the other is Comment, which is our browser. And all of those exist on like every platform that you can imagine. There's actually a lot to do, a lot to go 0 to 1 on still. But then there's like a lot to maintain and nurture. Anything that may be working, we need to make sure that we keep our foot on the gas. So it ends up being like, like I said, and none of this stuff really collides. So there's just a lot of things kind of firing in parallel.

Interviewer (8:13)

When you talk about the surface area like that, you start to realize that the number 31 is actually pretty small. But from a hiring standpoint, it's an impressive feat, right, to build a team not only of that size, but the quality that you've been able to reach is impressive. And I think everyone listening would agree that Perplexity is very much so cemented in kind of this top tier of design talent. It's a place that people want to work. So I'd like to try to reverse engineer that success a little bit if we can. So maybe we can kind of go back to the beginning when you're Thinking about the types of people you want to surround yourselves with, how the org could potentially shake out. Can you just go back and unpack some of your initial team building strategy?

Henry Modisette (8:55)

There's maybe like two, two parts of it. One is thinking about what skills that I know you would need to build a brand and to build a product. And then the other is just really being kind of thoughtful and consistent about what type of personality or what type of person, what archetype we need to get through this startup era. And you know, now there's like a, I would say we are in another era of like, okay, we're, we're a lot bigger than we used to be. How do we keep our agility? But also are people in the world that have designed products that, that have, you know, millions and millions of users and that's actually important knowledge to be able to bring into a team. You know, how do you make sure that, that everything works well and scales well and works in every culture in the world and things like that. There, there. That is like very different than 0 to 1. We really try to like bring in a mixture of people that have different expertise in that sense. On the skills side, the creative studio is pretty straightforward. We know we need to make things, so let's bring in people that know how to make that stuff. It helps to just be able to make something in house. It's like, okay, well we want to make better videos, let's bring in somebody else. How to do that? That ends up being a pretty straightforward consideration. Product is a bit of a challenge in finding the right skills because I want to bring in people that can kind of work on anything and do it quickly. I would say it's hard to find that type of person and it's hard to find someone who has just like, just the right amount of knowledge about AI or working on like a non deterministic product experience or is going to get it quick and trying to match that person with the problems we have. And you know, a lot of our more complex product surface areas like really benefit from someone who's a little bit more technical and maybe they're even writing code too. So the scaling of that and matching the skills. Every moment where we've decided to hire somebody that's like a consideration. It's like, okay, what are we really missing right now? The first calculation ever made was like it was just me and I wanted to hire a brand designer because I didn't do that very well, you know, so kind of like in every moment it's like okay, what do we wish we could do that we can't do today? Let's add a person that can do that. And you know, you can pretty much keep doing that forever. It's very rare that we are just like bringing someone in and not really knowing what they would do, if that makes sense. We definitely start very much from like a, how do we want to grow? Like, if you think of the design team as like a combination of capabilities and knowledge, like, what is the little point that's missing right now that we could grow on? So that helps like kind of make every new person feel like a really incremental addition to the team. I think the last part, I guess is just there's an archetype that I look for and a lot of it is just trying to match somebody to this company. The values that we have on product development and software creation, the trade offs that we make, the way we think about design, there's that stuff, there's the fact that we are a startup, we're scrappy, and you know, we, we, we go fast. And I definitely look for people that, that really want to work in that environment because it's quite different than working in a, in a, in a really large company. A common thing, not even just in design, but we are the underdog and some people want to work at a company like that and some don't. And we try to be really honest about that. Does that stress you out or does that fire you up? It's pretty binary and it's important to get that figured out. Like in the interview process, like, are you, are you, do you want to be in this position?

Interviewer (12:11)

Something you mentioned to me earlier was how you've directly hired every single person. You've been very hands on in this hiring process. So when you think about the interviews, like these conversations that you're having with people, what are some of the specific signals that you've been looking for and how has that evolved as the company has scaled?

Henry Modisette (12:32)

So at the beginning of the company, I was very intentionally trying to, like I said, like, find skills that I don't have because it just increases the output of the team in capability, you know, hiring for my weaknesses. I mean, one thing I learned on previous design teams I've been on, I felt like we always hired the same type of person, both in their skill set and, you know, the things that they could make because it kind of does in some ways make it easier to do, like staffing. If you kind of think, you think of everybody as having the same abilities, maybe Just at a different level. It makes staffing easier. But I wanted to take the opposite approach because I just felt like we could do more and have a more interesting outcome from like a, you know, the collaboration would be more interesting if everyone was actually completely different. And it's been nice because there's actually like naturally a lot of, you know, respect in the team for each other because everyone is so different in their background. You know, there's some people that come from big companies, some from like founding designers, some from agencies, some never even worked in tech before and now they are. We have a designer from NASA. I like having different types of people because there's just different perspectives on how to do things and people's eyes spot different things and think about process differently, whatever. And I really like working with designers that like, were founding designers at some point because I just think they get it. They don't mind the chaos of a startup. They don't mind the, you know, the lack of definition. What are we doing, why there's no prd? Like, there's just ideas. Let's just buy a transaction and start locking stuff up. Like, whatever, we'll throw it away. Okay, you got some feedback, Whatever. You know, there's just like a kind of confidence in the ambiguity that I think that people that have done that finding designer role, they just like, carry with them. But like I said before, we don't always need that. And now that we're bigger, it's like fun to add different types of people that really do think very differently about how to build a company.

Interviewer (14:22)

Speaking of the different types of designers, it reminds me of something that you mentioned the last time we talked where you said that you brought on a design intern that's starting soon. So what did you see in that person that made you want to take a bet on them? Especially given the fact that they don't have this breadth of experience.

Henry Modisette (14:38)

So when I was at Quora, we, we pretty much only hired new grads and had a lot of interns. And it's. Those are the most fun interviews to do because obviously interns don't know how to do anything. And so you're really trying to figure out what kind of person they are. The thing that I look for the most is do they have examples of invention or self learning? Because it's pretty easy to find someone who did their homework. But I want to find someone who didn't do their homework and did something else instead. Something that they weren't asked to do. Like, especially if you're interviewing students that's the most interesting student to find is someone who somehow for some broke the norm and went and like made an app on the weekend or something like that. They didn't get asked to do it. It wasn't like an assignment. So I love finding those people. And you only just need one little indication. Then you can take a bet on them. Sometimes, you know, you get kind of two versions of that person. They know they're a rising star and it goes to their head eventually that's like not a good fit. And then there are others that I think, like, kind of never let go of that, like, hunger and you know, kind of humble attitude. Like, okay, I have so much to learn. And for that person getting to join a team full of people who have, you know, 10 plus years of. It's like a dream scenario because there's just so much to learn and they, they absorb it. So I've gotten to see that a lot. I think like, hiring is a great gift that you can give a good job. Like, we all have to do work and to build a team and a job worth having and a job worth enjoying. To be able to find the right person and invite them to join, it's an incredible thing. And I think that's even more amplified for an intern because, like, it can change the trajectory of their career. Obviously, like, you're setting it right off the bat if you have, you know, a company that's exciting to work. It happened to me and I feel like morally obligated to, to be able to give that to other people.

Interviewer (16:20)

So was there a specific indication that you saw in this person?

Henry Modisette (16:23)

I do spend a lot of time just like browsing, looking for people. I always want to, like, keep an eye out. Where are you looking at people? I would say mostly, mostly Twitter. Still. I mean, I end up on, I don't know, I end up on portfolio sites for like a bunch of different reasons. Like people send me links and whatever. But in terms of me just like blindly peeking around, it still is Twitter. I found this person's website and just, I thought it was like a nice looking portfolio. And then I went and looked in and saw that she was still an intern or still in college. And that was like, that was exciting to me. I'm like, okay, I should just like reach out and see if there's any chance. I don't know, I always forget, like when internships happen. You know, every college works differently. So, hey, do you want to. Would you ever be interested in talking about. As simple as that. And I Guess what I saw was, you know, it's rare to find people that, especially early in the career that are good at multiple things. Like, I'm excited to find someone who seems really strong in one area. Could be like product thinking or visual design, or they can be very technical. Sometimes you find someone who somehow got good at multiple things. And I actually think young designers now are like so embracing the new tools that they have that they're like all getting good at a lot of things really quickly. Ultimately it's just reps, reps with feedback. And if you can get feedback, you can get really good really quickly. People are accelerating through their learning and their talent, like the ones that get it and are embracing it. It's pretty cool. So I think there's like a lot of rising stars right now. We'll have to find those people.

Interviewer (17:52)

I have the same experience browsing Twitter. It feels like every eighth post is some 19 year old where I'm just like, in six months you're going to be so much better than me.

Henry Modisette (18:00)

I just think about how when I was 19 using Photoshop, my days were slower. You know, like to go from idea to having a mock up was way longer than and let alone like a prototype. Like, whereas today you can have an idea and have a prototype and then you get feedback on that prototype and you can learn, you can adapt or whatever. So you're able to learn faster than before, just naturally because like the loops are quicker.

Interviewer (18:25)

What's credit Perplexity is quite a magnet for talent right now, but I kind of want to step outside of that and talk hypothetically to somebody who's listening. Maybe it's a founder, maybe it's a first designer and they're facing a little bit, bit of a cold start problem. They don't have this momentum. How should they think about different strategies for laying the foundation for a design team that would at least give them the potential to reach the level that you're at.

Henry Modisette (18:49)

I mean, it's definitely a hard problem. You know, there's a lot of startups out there and I've actually been asked this a lot and I feel like I have kind of like a generic answer, but it just requires a lot of taste, like throughout the process. But my simple perspective on this is it's important for a lot of reasons when you make a startup to stand out. The best way to stand out is to invest in, in your brand and your product. Because especially at the beginning of a company, what is a startup at the beginning? It's just a thing that you made up, you know, maybe you bought a domain, maybe you raised money, hopefully you've got a name. But it's like it is a thing that's in your head. You know, you have no users, you have no money, you have no revenue. And then when you're hiring, you're asking people to make a very important decision. I don't care, like, how big you are. People think that switching jobs is a big deal and it's like a bigger deal when you're joining a startup. I think people overthink about risk and they try to think like investors, like, what's the upside? Most people really are qualified and if they are qualified, they, they know that they aren't. At the same time, it's just like, you know, it's a gamble and you never know what's going to happen. But you're asking people to make this decision and you want to make them feel good about that decision. Right. And so a lot of, I think building a startup is just putting your mind on that other person's perspective, like, what do they want to feel? If you have no designers, I think the most important message you can convey if you're trying to find a founding designer is like, why is design going to help the company win? What's your theory as to why design matters? Because you can't just be like, oh, we need a craft designer, you know, obviously. But if you said, like, we can beat our competition because design will help us do that and we're like, fully committed to like using design as a weapon in the market through marketing, through product, we're going to beat them this way. That's going to be exciting value prop to somebody. So there's like a deep understanding that to some extent you have to have a strategic understanding of like, why design matters. You can't just say that it does. There's that cold start problem. To get that founding designer and to build a team beyond that, I think that message, like, will resonate with a lot of people, like, if you can keep refining it. But people also react to these very superficial things. I think when I was younger, I thought it was silly. I remember when Dropbox was considered a cool design place to work. And I remember at the time being like, it doesn't seem like a very interesting product. Why is everyone so excited to work there as a designer? I think it's more interesting that I gave it credit now that I'm older, but, but also like they, they did this really powerful thing which was just investing so heavily in their brand. And that that signaled to users that this thing was going to be more secure and robust and stable. Right. There's like a quality signaling that's happening, but it also was like tremendously effective for recruiting. Right. Because you're signaling that we're going to go and work a little bit harder. We're going to go the extra mile when it comes to design. We're signaling that design matters here. Obviously Apple does this too and it really works. And so I think it's like a very basic thing to emulate. Just push a little bit harder, show the world that you care a little bit more than everyone else. You're willing to, whatever it is, spend a little bit extra time, spend a little bit more money, whatever. Because that, that has the snowball effect. Because you have a message on why design will help you win, you're able to signal that like you're actually doing what you said you would do.

Rid (22:05)

Hey, really quickly let me tell you about the all new Dive Talent Network. I've hand assembled over a hundred of the most talented designers and builders that I know so I can recommend them to my favorite companies. So if you're listening to this and you're open to new opportunity opportunities, the Talent Network is anonymous and super low pressure. It's just an easy way to see what's out there without having to post on social media. So if you're interested in joining or maybe you're looking for your next hire, head to Dive Club Talent.

Interviewer (22:35)

Even just a personal anecdote. I have a lot of startups reach out to me to tap into the Talent Network and everybody's looking for founding designer.

Henry Modisette (22:45)

Yeah.

Interviewer (22:45)

And the first thing I do is I click through the website and you make a four second knee jerk reaction based off of the quality of the website. You know, that's just like human nature. And so yeah, gosh, if you don't have a designer, pay a good designer, totally.

Henry Modisette (22:58)

I think that's just like a basic trick. You have to think about that person's perspective. Like, do I want to join a company that's just going to diminish me when I get there or do I want to join a company that's going to help me be the best version of myself and also help me make the company successful. I want to hear why design matters because it's going to come out in the wash eventually if it doesn't. And I also just want to, you know, show, prove it. Like if you think design matters and you're trying to bootstrap a team, I think it really makes a difference if you pay a freelancer to like, make something really nice and then be like, boom, we're hiring designers. Like, check it out. We care. We know how to do it. We know how to like, ship good design. Because I think ultimately, no matter whether you're hiring your first Designer or your 50th, if the product is beautiful, people will want to join the company. Yeah, you can't fake it. You know, like, I've seen companies tweet out, like their design system website, and then you go to the product and it's bad. And it doesn't make me want to join the company. This is not a knock against anybody. It's really a knock against, like, you know, organizational paralysis that I know exist at a lot of the companies. A lot of products are poorly designed, but it has nothing to do with the design team, if that makes sense. It's really something else. It's organizational, you know, the way that organizations work. It's the way that the code is set up, like, whatever. There's a lot of reasons why a product may be not very nice. There are so many designers and so many startups. Something's wrong if everyone's like, not finding a match, you know, And I think a lot of that is just like, you know, telling the right story and founders understanding like, what even design is, because it's not putting ornaments on the tree, it's product strategy, it's brand strategy, it's company strategy. And, and it's the expression of that stuff and, and the expression of like, good product decision making. It's funny how many times I've been in not a crit, but like, I'm helping someone solve a problem and I'm just like, this is not a UI problem, this is a product problem. They need to make up their mind, like, what feature they want that will help every product be better with more confidence and decisiveness. And then if you've got someone that can make nice ui, then you're fine. There's like getting, getting the company to internalize, like the idea of what design is and how it's going to help the company win. That's like the first step. The second step is like signaling that publicly through execution. Could be marketing, site could be the product. Hopefully it's both. Could be investment in brand. I think like, the third step really has to be investment in brand because I really think, like, especially at the beginning of a company, people are not joining the company, they're joining the brand. That's just how like the World works. I mean, people. People are making a decision about who they think they are. If you tell a clear story with your brand, you're providing a narrative that, like, is going to resonate with people. You know, the story of perplexity is we make consumer products, we care about building an answer engine that. That helps you find, you know, find reliable information where we're kind of serious, you know, we're. We're kind of very thoughtful. There are these things that, like, are kind of coming out of the brand that attract a certain type of person that's intentional. If you can do that very, very clearly, like, as a startup, you're gonna start to find, like, a cohesive culture.

Interviewer (25:59)

I think I wanna switch and talk about you for a little bit because I know you had, you know, background as a manager at Quora, so it's not like your first time having people report to you, but this is a totally different set of. And opportunities dealing with, one, this kind of scale, but also two, just the total blank slate of a design work that you get to mold and shape according to whatever the heck you want to do. So before we get into some of the tactical things, who inspires you as a leader? Like, where did you look to figure out what type of leader that you wanted to become?

Henry Modisette (26:32)

I would say I've been fortunate enough in my life to only have good bosses, which I don't think anyone else I've ever met can say. My first boss ever, I was a camp counselor and she was a teacher. I realized, like, in retrospect, how much of an impact that had on me because it was like, me and her in charge of, like, 30 kids dealing with parents too, which is kind of a. A pretty intense type of customer to have. They're kind of scary and they care a lot. Her leadership style was just this sort of, like, quiet confidence, you know, like a real teacher. Just able to command a room with confidence and command the energy of a room with confidence. And she could, like, light everybody up and get everybody moving. When a parent came in and was frustrated about something, she was from Georgia and she would always just say, like, kill him with kindness or whatever. You know, she was just like, smile and whatever. Even though they were being really awful to her, I've always been inspired by that. Just pure, like, leadership. Me watching someone do that every day because I don't know, like, what her life was like and what her, you know, how. What her day, you know, did she have. Was she tired that day? It doesn't matter, right? She's Got to keep all these kids safe and excited. Within my design career, I, again, just, like, kept having good bosses. I had a few people when I was. When I was doing, like, internships, I had a few people who really kind of pushed me on craft. One of them actually works at Perplexity now. His name's Champouri.

Interviewer (27:53)

Oh, cool.

Henry Modisette (27:54)

I didn't know that he was my intern mentor. Now he's on my team, and I'm just, like, so happy to get to work with him again. There are people that. That just showed me how to push, if that makes sense. Like, when you're young, you want to. You want to be better. You have no idea how you can see the difference between your work and great work, then you're going to be fine. As long as you listen. If you can't see the difference, then you're never going to get there. When I was at Quora, I had two bosses. One, her name's Rebecca Cox. I think she's a legend. She showed me you can really think completely differently than everyone else in terms of how to do product design, how to do process stuff. When I was at Google, we did, like, you know, the art school thing. You make mocks in Photoshop and you print it out and you put it on a board and everyone, like, gives feedback. You know, with Rebecca, she would ask us to code everything, build a prototype, send me a link, and I'm gonna use it. That, like, you know, immediately just clicked for me. Like, I'm like, wait a second. Yeah, this. We're making software. It's interactive. It's got states and flows. And she just, like, always had this kind of punk rock mentality. A little bit of, like, you know, everyone else is wrong. You don't. You see that? And that works for me. You know, I like that you don't have to do what everyone else is doing. I think that's, like, the most important thing. And actually, in fact, if you do the opposite, even arbitrarily, like, that might be your advantage. And that's something that I definitely carry through as leader. It's just a reminder everyone else might be wrong. Let's consider that at least that's exciting for a lot of people, to be honest, that the notion that, like, maybe there's another way.

Interviewer (29:30)

Are there ways that that punk rock mentality has rubbed off on you and ultimately shaped the practice of design at Perplexity?

Henry Modisette (29:38)

Yeah, for sure. I mean, I. I do think, like, she was 100% right on, like, how to make software using a static image. Tool to, to make software doesn't make any sense. First principles. You do have like a strong bias towards prototypes and a lot of design team codes and things like that. The other thing is just, just perspective that you have to be obs like how things work more than what they look like. That is very Quora as like a product design mindset consequences. A lot of Quora stuff didn't look very good, but like it was so thoughtfully constructed. You know, we, we built some amazing systems. We learned a lot about like product building, like real product building. I mean that's what building a social network is. It's. A social network is only defined by how it works. If you look at Twitter, like tweet length completely changes how people behave. And even with the same character limit, you know, you have different information density per character in different languages and then you get different behavior. When Twitter had its character length limit, the English usage was behaviorally totally different than Japanese just because the characters had different information in them. That's what a social network is. And you got it. You got to just make a ton of decisions, how does it work? And so anyways, I think like having that be drilled into me, like which is so different than design is nice, but buttons and animations and picking colors and whatever, getting into like actually building an interactive thing that, that, that led to behavior. Quora like really was more like urban planning, which was an amazing, amazing thing to, you know, to get to build a social network. Actually, like most designers have not gotten to do that. You know, there's not that many social networks that have ever gotten up to a million users. So a lot of just that has influenced me not only like how we had to work, work, but just the mindset of like, we need to completely adapt the way that we're working to the problem that we're solving. There is not like a design process that is a universal concept. There's problems and you know, there are people who figure out how the software works and they need to follow whatever process is going to help them do that. And I just love that the idea that the way that we were working made sense, but the way that like Apple was working also made sense. And it doesn't matter, it's just, just, you know, an adaption to the problems that we're working on at Perplexity. Like we actually are solving so many different types of problems and kind of need to put on different approaches. Some stuff we're doing is much more Apple, some of it's much more Quora. And being able to, like, identify, like, which one's which is really valuable.

Interviewer (32:07)

That's something I've been thinking a lot about recently, is as a designer. Obviously there's creativity in the output and whenever you are making. But more so than any point in my career, I'm finding so many opportunities for creativity in the process. And even stepping back and thinking about how do I want to attack this problem. There are way more options at my disposal than I've ever felt before. And being creative about which path I want to take is really energizing. And I feel like it's just exponentially increased even in the last year.

Henry Modisette (32:38)

The final leader that I worked under at Quora was David Cole, and he was just getting us all to think about game design as, like, actually the most useful reference. There's this framework called mechanics, dynamics and Aesthetics that is like a game design framework for making decisions. He was tuning us all into that because it, like, really felt much more useful as a way to think about building a social network. And that was exciting just being exposed to, like. It's like, oh, there's like a whole other room over here where we get to think about design completely differently. You know, we've been doing it enough to know that picking colors and fonts and buttons, it was just not helping, like, make the social network better. You know, that that stuff really is just the interactive layer, and it's not even one that you want to innovate on very much because, like, people just need to click stuff and read stuff. My broad message from that experience was just I got exposed to just people who are really, truly thinking differently and good at teaching the rest of the team to think differently. And that's just like a very different environment to be in than, I think, a lot of design teams, maybe, where there's like a director who's just like, pushing everyone to, like, line up their boxes, fix the spacing, you know, it is like a completely different working environment. Both are valuable, and we try to have both happening at perplexity. But the diversity of people that I've been exposed to and their way of thinking about design has served me very well.

Interviewer (33:59)

Something I associate with you is being a leader who is prone to just keeping hands in the clay, and you're a maker at heart. And that being said, you're scaling at a rate and seeing this expanding surface area and a full product suite, it's impossible, right, to have your hands in the clay at all times. So there's an allocation decision that I'm sure that you're kind of wrestling with a little bit. So can you talk a bit about how do you think about where to invest your time and where does it make sense to really get into the details?

Henry Modisette (34:31)

Something I believe is that, you know, to be a good designer it needs to be hard. You need to make a lot of decisions and you need to own those decisions. I really want everyone on the team to just have to deal with that because it's going to make them better. I want everyone to have like a lot of ownership, a lot of accountability, therefore a lot of trust from me and from the company to figure it out. Because if you have to make a lot of hard decisions every day, you're going to become a better designer. It is the best thing for the org for me to just throw everyone in the deep end, but give them a way to ask for a backup if they need it. Because the alternative I think is like using everyone as like a tool for my brain. Like if I go in and start directing everybody all the time, that that probably doesn't scale well, but it also like does. It prevents growth, I think from everyone else. A lot of people on the team are much better than me at a lot of different things and so I want to let them be the best versions of themselves. So the way that I think about all of this is like I want a lot of parallel work happening where it's happening in a very independent way and you know, I should be able to like not exist and it should all still be working. I care a lot about building having like a self functioning team and a culture more than me being like required for anything to work. Now this is hard to do, but it's got so much more upside than, than one where I'm like manually pushing everybody all the time. I try to make sure that like everyone isn't feeling like they're like completely abandoned or anything. But yeah, most of my job is just trying to set everybody up for success and just floating around, making sure that they have what they need and encouraging them to just keep going. You know, there's like a confidence that I bring that just like biases everyone to like keep moving. So it's hard, it's hard to like, you know, there naturally there are people that just like I don't interact with as much as others because of like what's happening. But I want, I want the team to be you know, like a machine that just operates without my intervention.

Interviewer (36:28)

It reminds me of something else that you said to me earlier where you talked about how when you're Working at a company that is scaling, the graph pretty much just keeps going up and to the right no matter what. As a result, it's not that you can run these really accurate experiments because the graph is never really going down at the end of the day unless you're looking at a super micro level. So in order to be decisive, you can't really just rely on what the data says. You kind of got to go with your gut, I'm assuming. So how does a designer grow that muscle? And maybe using, I don't know, the intern as a hypothetical, like what are some of the ways that you would either invest in that person or hope to see them grow in their not only ability to be decisive, but to hopefully make primarily correct decisions.

Henry Modisette (37:14)

It's tough because like, you know, it's ultimately it is quite subjective. Right. Is you know what is correct? Is it because is it people use the product more or is it that like you never heard any negative feedback from anybody? It's really tough because there's so many trade offs and I think the most important thing is like just never getting stuck, never stalling, like because you could, if you're constantly moving, constantly just, just making the best decision you can, the best trade offs you can, you can always revisit something next week. Never losing the, the muscles around, around shipping and being decisive. I think it's fine to be wrong. And I've been doing this enough to know like that we just don't know all the time. We can't.

Interviewer (37:54)

Yeah.

Henry Modisette (37:55)

And I think what makes a good designer is someone who is able to like, you know, survey the possibility space quickly and just make a decision that balances like the trade offs and keep going. That ends up being much more valuable to the organization than someone who goes back into the drawing board and explores 50 more ideas. It's unlikely that you're going to end up somewhere like that much better. And instead maybe you could have maybe launched three more things in the meantime. I think some work can be measured. We do ab test things when we can, when we think it's going to help. There's a lot of things we just make decisions on and it's just better to be decisive. There's a kind of cultural value of the company around decisiveness and clarity.

Interviewer (38:36)

Let's dig into the culture a little bit. You used the phrase growing up earlier, so I kind of want to unpack what fits into that bucket for you. My assumption is that there's a lot of fluidity in terms of how you all operate. You've brought in people who are experienced, who are given this level of autonomy. On the flip side though, are there certain behaviors or methods of collaboration that you really, really push for that do kind of form this level of structure in terms of how design oper at perplexity?

Henry Modisette (39:08)

I don't want to just fall into like the habits that other companies have. Maybe they're right, but we know the consequences of those. You know, like, we know the consequences of like structured Wednesday design crits. It means you wait till Wednesday to get feedback. It means that, you know, there's a performative nature to giving that feedback. I know the consequences of that. So why don't we try something else and let's like, I would rather find out, you know, the consequences of some other model and maybe we find something that works in the middle. This is like the most competitive software market ever and we had to look for any way to compete. I think therefore, like, you know, every, every kind of normal thing should be like challenged because maybe you find like a different way to work, different way to think and way to unlock a little bit more from everybody. And, and so that's kind of like my, that's always been my mindset going into building, building this team is like, we gotta find our edge, you know, we gotta find any advantage we can because the design team has to help make this company successful. And people love that, right? They want to hear that. They're, they're excited to switch it up to try different things. I mean, everybody knows what doesn't work about the like, average process at other companies. So let's try different things. I kind of have this mindset of like, let's just keep it as organic as possible and just like see what emerges, you know, So I, I'm pretty experimental with it and, and it's cool to see what works, what doesn't work, what breaks. And then we try to formalize things that do seem like they're working.

Interviewer (40:34)

Are there specific operational edges that have emerged?

Henry Modisette (40:37)

I do think our embrace of like fully organic crit and feedback has helped us like move very quickly. I think just in general, embracing agility and velocity as like, like the most important values for the design team. That's like a unique thing to say. That's more important than anything else because that makes people uncomfortable. What about quality? I would rather, you know, you can flip it, right? Like, let's just, let's just say like the most important thing is to go fast and therefore how do we maintain quality as like a follow up on that? I think Just that mindset has helped us, like, keep the company going at the pace that it needs to go. Because a lot of companies, I think, are slowed down by the design team.

Rid (41:17)

Team.

Henry Modisette (41:17)

I don't want to have that on my list. So that's like, a big thing. There are certain things we do like, you know, more embracing, very technical designers to just, like, go and, you know, change the product when it needs to get changed, you know, so there's a lot of, like, lack of process. That's been an advantage, but it can be a disadvantage too, because it leads to like, potentially just, like, messiness, projects that. That should be collaborating, better design system problems, things like that. It's like kind of a constant puzzle, always just trying to make sure that. That things are working well.

Interviewer (41:45)

You talked about the importance and also the fluidity of feedback a few different times. But can you shine a light on what does it actually look like in practice? Like, how do designers have perplexity, get feedback?

Henry Modisette (41:56)

So there are people that maybe have a lot of context at what you're working on and people with less. 1. I ask everyone to just think, when do you need feedback? When is it actually useful to you? Because sometimes feedback is extremely important at the beginning, at the end, not often in the middle. And sometimes it's not important at all. And, you know, so if you're, if you're always thinking, like, I'm responsible for this thing, I'm responsible for the success, the quality. I'm out here on my own, I have to figure this out. But that's clear to you. But you've got, like, plenty of phones to ring if you, if you want, you know, you can call for help or feedback, whatever, at any moment. Then people just, they. They use it accordingly, you know, so there's a lot of, like, is anyone around right now to jam on this? You know, like, there's just that kind of messaging, happens in person, happens on online. It's just there's this sort of daily, organic, like, depending on the state of the project, people collaborating, and it could go on for 20 minutes, it could go on for two hours. It really just depends on what's going on. It's kind of as simple as that, I think. But it only works when people feel like it's their decision.

Interviewer (43:01)

Yeah, I like that. Everything kind of always keeps coming back to ownership and being decisive.

Henry Modisette (43:05)

Everything has to be consistent, right? Like, I can't just be, like, telling people what to do all the time, but then. Then I have to tell them to get feedback. I need people to know that, like, that's the tool they're supposed to use themselves.

Interviewer (43:16)

Before I let you go, I want to zoom out and kind of reflect on the future of the design team and where this is all headed. And when you think about those potential future outcomes, are there versions of the future design team that you're actively trying to avoid and what are you doing to navigate the team successfully?

Henry Modisette (43:35)

I mean, the big thing is like, I want the product to be great always, you know, and I, and I want it to be evolving quickly, always. That gets harder and harder as you become bigger, you know, like design team, company, whatever. Because we have to be careful. Like, we don't want to break stuff. We want to make sure that we're following good engineering practices, following good design systems practices, not creating too many roles with the design system, but creating just enough that people can be decisive. There's a lot of challenges that come with scale and you can totally see why companies have evolved the way that they do. And like I said, I've definitely been trying to reflect as often as possible. Like, do I need to change my values? Am I a startup designer? Because that's all I really know. Can I lead a 50 person design team? Because there's a point where I don't even, I don't have anything to reference. I'm listening to my team on like, what they think they need and trying to construct it for them. But I like that challenge and I think I can figure it out. If other people can, why not me?

Interviewer (44:34)

I love that mentality. If other people can, why not me?

Henry Modisette (44:37)

There's like a really good sports phrase, pressure is a privilege that's been in my head lately. If I'm in this position, that's a gift to be in this spot, right? And like, the fact that it's hard is, is actually a wonderful thing. The quote is like, if it's. It's like pressures are privilege and champions adjust. You know, it's like there's a. I think it's Billie Jean, she's a tennis player. I love that. If you're going to have that pressure, like, you might as well make the most of it. It's hard to know, like, you know, when you're in uncharted territory. Personally, not many people can give good advice, but you can at least like get their perspective on like what they did in the past. And then you can kind of create a composite of what you should do. The thing is, like, there's a lot of organizations in the world to learn from, you know, whether it's like companies or like, I don't know, the way movie studio works, like, the way that the military is set up. Like, I don't know, there's so many examples of how humans are organized, so plenty to learn from.

Interviewer (45:30)

You're making me realize there's kind of this spectrum where on one end you kind of figure out what shape you want this to take and you make it happen. And on the other, you are a little bit more reactive and maybe placing a greater emphasis on just having a pulse on what's the team asking for, what behaviors are naturally emerging. And as a leader, maybe you actually feel like you kind of have to be intentional about where you want to fit on that spectrum.

Henry Modisette (45:54)

When I hide a good leader, it feels like they know something about the universe that I don't know. And it may be like, all in my head, but it's fun to work for somebody where it just feels like they know something, like they know what to do, they know what's going to happen next. They have a plan, and there's like a confidence. There's something about that. And I always felt that like. Like from the people that I worked for in the past. And I want to convey that, you know, like, so you can't go up and be like, I don't know what I'm going to. I don't know what's going to happen next. Like, I'm, you know, you can't show that. But I think it's also important to be like, you know, to show humility.

Rid (46:27)

Right.

Henry Modisette (46:28)

And so I try to do that by consulting everybody.

Interviewer (46:31)

Do you feel like you know something about the universe?

Henry Modisette (46:33)

Of course I do. So I'm going to hold, you know.

Interviewer (46:37)

Well, I appreciate you coming on and kind of giving us an update on all of the things that are happening, the pace at which it's happening, how you're growing as a leader, even the state of the design team. I think a lot of people listening to this look up to everything that you all are doing, and I appreciate you sharing it with us today.

Henry Modisette (46:54)

Thanks for having me.

Rid (46:55)

Before I let you go, I want to take just one minute to run you through my favorite products. Because I'm constantly asked, what's in my stack. Framer is how I build websites. Genway is how I do research. Granola is how I take notes during crit. Jitter is how I animate my designs. Lovable is how I build my ideas in code. Mobin is how I find design inspiration. Paper is how I design like a creative. And Raycast is my shortcut every step of the way. Now, I've hand selected these companies so that I can do these episodes full time. So by far, the number one way to support the show is to check them out. You can find the full list at Dive Club Partners.