Henry Modisett - Inside Perplexity's design culture

Someone asked me recently, "If I had to join a design team, where would I want to work?" And the answer was pretty easy

to work?" And the answer was pretty easy for me. It's perplexity.

for me. It's perplexity.

>> You have to have a strategic understanding of why design matters. You

can't just say that it does. What's your

theory as to why design matters? Cuz you

can't just be like, "Oh, we need a crack designer," you know, obviously. But if

you said, "We can beat our competition cuz design will help us do that and we're like fully committed to using design as a weapon in 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, what exactly makes their design culture so special and what are the things that they're doing to attract the top tier of talent?

>> 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.

>> Welcome to Dive Club. My name is Rid and this is where designers never stop learning. This week's episode is with

learning. This week's episode is with Henry Modiset, who's [music] the VP of design at Perplexity. And on top of doing a deep dive into their design culture, we're also going to get a

little behind the scenes of Henry's journey as a design leader because a lot has changed since the last time that we talked. One of the hardest parts about

talked. One of the hardest parts about rapid growth, which is like an incredible gift, [music] you know, both growth in terms of company and amount of users and things like that, uh, one of

the hardest parts is kind of like knowing to what extent you need to change who you are. There's a way that you work. There's a set of values you

you work. There's a set of values you have to hold. There's a lot of trade-offs you have to make that get you through that period. And then there's a point where like you've got something going, you know, you're you've got PMF,

you've got network effects, you've got exponential growth, whatever. You're

also something that people rely on for their job to make important decisions.

And maybe those values that got you to that point are like actually worth revisiting. When you're early on in your

revisiting. When you're early on in your startup, you really need to make like a lot of trade-offs around, you know, velocity, quality, like you know, you want to just ship and learn, like the

whole move fast, break things, whatever.

When you get bigger, you you need to be careful because you're not trying to gain a user, you're trying to keep a user. Well, you're trying to do both at

user. Well, you're trying to do both at the same time. you do need to like start to work differently and think differently and have different processes, maybe even hire different types of people. And it's really hard to like know when you've shifted into that

new world, especially if it's happened really fast. The amount of change that

really fast. The amount of change that we've experienced in the last year is new to me. We've gone from being a startup to like a real choice in the

world, uh, an important app that people use every day. And that's that's profound. And and so that that's like

profound. And and so that that's like the main thing that I've been like trying to reflect on I guess lately and you know in the last year is like well who were we what what do we need to change about you know how we talk about

ourselves, how we do the work, what processes we follow. Real quick message and then we can jump back into it. Fun

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to start building. Okay, now on to the episode. We'll get into the size of the

episode. We'll get into 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

other people. Where do some of the biggest deltas exist? like can we go one level deeper? What are the biggest

level deeper? What are the biggest changes that you see when you kind of reflect on these two points in time?

>> One, we're doing a lot more every day.

And the second is we have to reconcile the fact that we're doing a lot more every day. the doing more is is allowing

every day. the doing more is is allowing us to do more specialized things, you know, on our uh creative studio side of of the house where we have people doing like motion design and video production

and um 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 inhouse 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,

parallelization. I mean, fortunately, there's there's this 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 ask for. There's very little collision, you

for. There's very little collision, you know, from a product perspective between the features. If you've worked on like a

the features. If you've worked on like a feed or 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 users 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

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

like that. But you know the consequence of 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 uh 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. I want to go a lot deeper into what this era of growing up looks like. I think I'm going to put a

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?

>> We have uh I would say like three suborgs of the design team. There's we

call it our creative studio. They're

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 in countries all over the world. So, they're quite busy. We also

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 uh or Laldo. The the second org, which is the smallest one, is our operations side hops. That team just kind of keeps keeps everything running

and functional. It's uh very meta uh but

and functional. It's uh very meta uh but very important. So that that's how we

very important. So that that's how we are able to do all of that creative work and do it on time, do it in a coordinated way. Uh it also lets us run

coordinated way. Uh it also lets us run our merch store, Perplexity Supply. So

that's run by the ops team. The third

suborg is product design. I would kind of cut it between like three different products. One is perplexity the consumer

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

imagine. There's actually a lot to do a lot to go 0ero to one 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

really collides. So there's just a lot of things kind of firing in parallel.

When you talk about the surface area like that, you start to realize that the number 31 is actually pretty small.

[laughter] 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

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. And 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

shake out. Can you just go back and unpack some of your initial team building strategy? There's maybe like

building strategy? 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

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

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 there are people in

agility? But also there are people in the world that have designed products that that have uh 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

that is like very different than zero to one. We really try to like bring in a

one. 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

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

better videos. Let's bring in somebody knows how to do that. that ends up being a pretty straightforward consideration.

Product is a bit of a challenge in 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-eterministic product experience or is going to get it quickly and try to

match that person with the problems we have. then you know a lot of our more

have. then 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

the scaling of that and matching the skills every moment where we've decided to hire somebody that's like a consideration 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 if that makes sense. We definitely start very much

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 that helps like kind of

grow on. So that 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, uh the trade-offs that we make, the way we think about design. There's that stuff. There's the

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 cuz it's quite different than working in a in in a really large company. A common thing, not even just

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

interview process. Like are you are you do you want to be in this position?

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? So at at the beginning of the

scaled? So at 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 um in capability. Um

you know hiring for my weaknesses. I

mean, one thing I learned in 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 cuz it kind of does in some ways make it easier

to do like staffing. If you kind of think if you think of everybody as having the same abilities, maybe just at a different level, it makes staffing easier. But I I wanted to take the

easier. But I I wanted to take the opposite approach cuz I just felt like we could do more and have a more interesting outcome um from like a you know, the the collaboration would be more interesting if 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 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

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

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 mocking stuff up.

Like whatever. We'll throw it away.

Okay. You got some feedback. Whatever.

you know, there's just like a a kind of confidence in the ambiguity that I think that people that have done that founding designer role, they just like carry with them. But like I said before, we don't

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 that really do think very differently about how to build a company. 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 by an intern that's starting soon. So, what did you see in

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?

>> So, when I was at Kora, we we pretty much only hired new grads and had a lot of interns. Um, and it's those are the

of interns. Um, 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

anything. And so, you're really trying to figure out what kind of person they are. The thing that I look for the most

are. The thing that I look for the most is do they have examples of invention or or self-learning? cuz it's pretty easy

or self-learning? cuz 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 reason 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. I love finding those people and 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 experience it's like a dream scenario because there's just so much to learn and 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 and a job worth

having and a job worth enjoying to be able to find the right person and and 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 for. It happened to me and I feel

work for. It happened to me and I feel like morally obligated to to be able to give that to to other people. So,

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

>> I do spend uh a lot of time just like browsing looking for people. I always

want to like keep an eye out. Um I've

been mostly mostly Twitter still. I

mean, I 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 [ __ ] around, it still is Twitter. I found this person's

website and just I I thought it was like a nice looking portfolio. Um 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 I always forget like when internships happen you every college works differently. So hey do you want to

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 is 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 that get it and are embracing it.

It's pretty cool. So, I think there's like a lot of raising stars right now.

We'll have to find those people.

>> I have the same experience browsing Twitter. It feels like every eighth post

Twitter. It feels like every eighth post is some 19-year-old. I'm just like, "In 6 months, you're going to be so much better than me." 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 mockup was way longer than and let alone like a prototype.

Like whereas today you could 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.

Let's clear that 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

listening. Maybe it's a founder, maybe it's a first designer and they're facing a little 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? I mean, it's 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. Um,

and I 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

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

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

company. What is a startup at the beginning? It's just a thing that you

beginning? It's just a thing that you made up. You know, maybe you bought a

made up. You know, maybe you bought a domain, maybe you raised money, hopefully you 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 are really are

upside. most people are really are qualified and if they are qualified they they know that they are at the same time it's just like a 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 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? Cuz you can't just be like, oh,

matters? Cuz you can't just be like, oh, we need a crack 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 in the market through marketing, through

product. We're going to beat them this

product. We're going to beat them this way. That's going to be exciting value

way. That's going to be exciting value prop to somebody. So there's 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

matters. You can't just say that it does. there's that cold start prompt to

does. there's that cold start prompt to get that founding designer and to build a team beyond that. I think that message like will resonate with like 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

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

designer? I think it's more interesting that I gave it credit now that I'm older. But but also like they they did

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

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

harder. We're going to go the extra mile when it comes to design. we're signaling

that design matters here. Um, obviously

Apple does this too and and it really works. And so I think it's like it's

works. And so I think it's like it's like a very basic thing to emulate, you know, just like push a little bit harder, like show the world that you care a little bit more than everyone else. You're willing to whatever it is,

else. You're willing to whatever it is, like spend a little bit extra time, spend a little bit more money, whatever, because that that has a snowball effect because you have a message on why design will help you win. You're you're able to

signal that like you're actually doing what you said you would do. Hey, really

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>> 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 >> and the first thing I do is I click through the website

>> and you make a 4se secondond knee-jerk reaction based off of the quality of the website. You know, that's just like

website. You know, that's just like human nature. And so,

human nature. And so, >> yeah, >> gosh, if you don't have a designer, >> pay a good designer.

>> Totally. I think that's just like a basic trick. You have to think about

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

successful? I want to hear why design matters because it's going to come out in the wash eventually if if it doesn't.

And I also just want to, you know, show prove it. Like if if you think design

prove it. Like if 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, you you like I've seen companies tweet out like their design system website and then you go to the product and it's bad and and it doesn't make me want to join the company. This is not a knock against

company. This is not a knock against anybody. It's really a knock against

anybody. It's really a knock against like, you know, organizational paralysis that that I know exists at a lot of the companies. A lot of products are poorly

companies. A lot of products are poorly designed, but it is nothing to do with the design team, if that makes sense.

It's really something else. It's

organizational, you know, the way the organizations work. It's 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 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

cuz it's not putting ornaments on the tree. It's product strategy, it's brand

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-m. It's funny how many times

decision-m. 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

they want. That will help every product be better with more confidence and and decisiveness. And then if you've got

decisiveness. And then if you've got someone that can make nice UI, then you're fine. There's like getting

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,

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

consumer products. We care about building an answer engine that that helps you, you know, find reliable information. We're we're kind of

information. We're we're kind of serious, you know, we're we're kind of uh 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

of person. That's intentional. If you

can do that very very clearly like as a startup, you're going to start to find like a cohesive culture. I think

>> I want to switch and talk about you for a little bit because I know you had, you know, background as a manager at Kora, so it's not like your first time having people report to you, but this is a

totally different set of challenges and opportunities dealing with one, this kind of scale, but also two, just the total blank slate of a design 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?

>> 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 CAP counselor and she was a

teacher. I realized like in retrospect

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

everybody moving. when a parent came in and was frustrated about something, she was from uh Georgia and she would always just say like kill them 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 cuz 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 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 Propsy now.

His name is Champuri.

>> Cool. 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

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. If you can

better. You have no idea how. If 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 Kora, I had

two bosses. One, um, her name is Rebecca

two bosses. One, um, her name is Rebecca Cox. I think she's a legend. She showed

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

process stuff. When I was at Google, we did like, you know, the art school thing. You make mocks in Photoshop and

thing. You make mocks in Photoshop and you print it out and you put it on the 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 going to 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 I and I and that that works for me, you know. I I 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 is 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. Are there ways that that

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

>> 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

make software. Using a static image tool to to make software doesn't make any sense. First principles. We do have like

sense. First principles. We do have like a strong bias towards prototypes and a lot of design team codes and things like that. The other thing is just this

that. The other thing is just this perspective that you have to be obsessed with like how things work more than what they look like. That is very Kora as

like a product design mindset.

Consequences. A lot of Corora 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

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

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. You got to 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 buttons and animations and picking colors and whatever getting into like

actually building an interactive thing that that that led to behavior. Kora

like really was more like urban planning which was an 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 like two million users. So a lot of just that has influenced me not only

like how we had to 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

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, you know, an

doesn't matter. It's just, you know, an adaption to the problems that we're working on. At Perplexity, like we

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 Corora. And being able to like identify like which one's which is really valuable. That's something I've

really valuable. 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.

>> 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

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

making decisions. He was tuning us all into that because it like it 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 u 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 about 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

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, they it is like a completely different working environment. Both are valuable

working environment. Both are valuable and and we try to have both happening at Perplexity. But the diversity of people

Perplexity. But the diversity of people that I've been exposed to and their way of thinking about design has served me very well. Something I associate with

very well. 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, if you're scaling at a rate and 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

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?

>> Something I believe is that, you know, to be a good designer, it needs to be hard. You need to make a lot of

hard. You need to make a lot of decisions and you need to own those decisions. I really want everyone on the

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

need it. Because the alternative, I think, is like using everyone as as like a tool for my brain. Like, if I go in and start directing everybody all the time, 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 I care a lot about

building like a selfunctioning 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

>> [clears throat] >> uh just like biases everyone to like keep moving. So it's hard it's hard to

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 um because of like what's happening but I want I want

the team to be you know like a machine that that that just operates um without my intervention. It reminds me of

my intervention. 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 and no matter

what. As a result, it's not like you can

what. As a result, it's not like 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

assuming. So, how does a designer grow that muscle? and maybe using I don't

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. It's tough

because like you know it 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 cuz you could if if you're

constantly moving constantly 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.

the time. We can't.

>> 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

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 like maybe launched three more things in the in the meantime. I think some some work can be

meantime. I think some some work can be measured. We we do AB test things when

measured. We we do AB test things when we can uh when we think it's going to help. There's a lot of things we just

help. There's a lot of things we just make make decisions on and and it's just better to be decisive. There's a there's a kind of cultural value of the company around decisiveness and clarity.

>> Yeah, let's dig into the culture a little bit. You used the phrase growing

little bit. You used the phrase growing up earlier, so I'm kind of want to unpack what fits into that bucket for you. My assumption is that there's a lot

you. My assumption is that there's a lot of fluidity in terms of how you all operate. You've brought in people who

operate. You've brought in people who are experienced who are given this level of autonomy. On the flip side though,

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 operates at perplexity? 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

feedback. I know the consequences of that. So why don't we try something else

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 have to look for any way to compete. I think therefore like you know

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, a different way to think and way to unlock

a little bit more from everybody. Uh and

and so that's kind of like my that's always been my mindset going into building building this team is like we got to find our edge, you know, we got to find any advantage we can cuz the design team has to help make this

company successful. And people love

company successful. And people love that, right? They want to hear that.

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

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'm pretty experimental

you know? So, 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. Are there

specific operational edges that have emerged? I do think our embrace of like

emerged? I do think our embrace of like fully organic grit and feedback has helped us like move very quickly. I

think just in general embracing agility and velocity as like the most important values for the design team. That's like

a unique thing to say. That's more

important than anything else cuz 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 followup on that. I think just that mindset has

that. I think just that mindset has helped us like keep the company going at the pace that it needs to go cuz a lot of companies I think are slowed down by the design team. I don't want to have that on my list. So that's like a big

thing. There are certain things we do

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 to try to make sure that things are working well.

>> 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 at Perplexity get feedback? So there are people that maybe

feedback? So there are people that maybe have a lot of context where you're working on um and people with less one I I ask everyone to just think when do you need feedback when is it actually useful to you because sometimes feedback is

extremely important you know 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 that's clear to you but you've got It's 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

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 a 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 2 hours. It it really just depends on what

hours. It it really just depends on what 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.

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

>> 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.

>> 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 you when you think about

headed. And you 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? I mean, the the big

team successfully? I mean, the 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

careful. Like we don't want to break stuff. We want to make sure that we're

stuff. We want to make sure that we're following good engineering practices, following good design system practices, not creating too many rules of the design system, but creating just enough that people can be decisive. There's a

lot of challenges that come with scale and and you can totally see why companies have like evolved the way that they do. Like I said, I I've definitely

they do. Like I said, I I've definitely been trying to reflect as often as possible like, do I need to change my values? Am I a startup designer? Cuz

values? Am I a startup designer? Cuz

that's all I really know. Can I lead a 50 person design team? You know, cuz 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?

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

wonderful thing. The quote is like if it's it's like pressure is a privilege and champions adjust, you know? It's

like a there's a I think it's Billy 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 un 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 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 a

m 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.

>> Yeah. 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.

When I've hired 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

happen next. They have a plan and there's like a confidence. There's

something about that. And and I always felt that 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 know what's going to happen next. It's like I'm, you know, you can't

next. It's 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, right? And so, um, I try to do

humility, right? And so, um, I try to do that by consulting everybody.

>> Do you feel like you know something about the universe? Of

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

[snorts] 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.

[music] Thanks for having me. 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 [music] my stack. Framer is

how I build websites. Genway is how I do research. Granola is how I take notes

research. Granola is how I take notes during crit. Jitter is how I animate my

during crit. Jitter is how I animate my designs. Lovable is how I build my ideas

designs. Lovable is how I build my ideas in code. Mobin is how I find design

in code. Mobin is how I find design inspiration. Paper is how I design like

inspiration. Paper is how I design like a creative. And Raycast is my shortcut

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.comclub/partners.