Tome's Henri Liriani | Hiring Startup Design Teams

Hi everyone. Welcome to Grey Matter, the podcast from Greylock, where we share stories from company builders and business leaders. I'm Heather Mack, head of editorial at Greylock. When many of us think about the foundational roles in a technology startup, job titles like engineer, product manager, or sales come to mind. But in recent years, design has become a much more integral and critical part of startups. And at increasingly earlier stages. Past generations of startups could get away with focusing purely on the technical aspects of their product in the initial stages and bring in design teams later. But today's startups are living in the age following an explosion of consumer apps and the subsequent push for consumerization of enterprise software, which has resulted in a heavy focus on the end user experience. Good design is now a critical part of a company's success. So how can startups bake design into the core of their product? And how should they approach building a design team? Here today to answer those questions are my colleague Katie Amaya, who's part of the talent team at Greylock, and Henry Liriani, who is the co founder and chief product officer of Storytelling platform Tome. Katie. Henry, thanks so much for being here today.

Thanks Heather.

Thanks Heather.

So Henry, you're among the few founders we know with a design background, so I think it will be helpful to our listeners to start off with some context about how the role has evolved over time. So you started off your career at a few design firms, you were a co founder at a music sharing startup and then you spent six years at Meta in product design before you co founded Tone, which we'll talk about in more detail shortly. From your perspective, how does design fit in the overall aim of a company's product and how has that changed?

Years ago there was often this like UI design or UX design split and that that was sort of a byproduct of how long it took to do each part. Back then, given the tools we had access to, you had someone wireframing, you know, all the steps in a workflow and you had someone visualizing all of that UI in like some like almost photorealistic graphical style like wood or metal or plastic. Now given how sort of the style that we use has evolved, the tools that we use to generate these designs have evolved. One person can do all of that like much more efficiently. And it turns out that having all of that thinking under sort of one roof produces better product outcomes too, because you can really closely coordinate product decisions and workflows with how something looks and how it works. And the truth is that those things aren't really that separate.

So tell us exactly what Tome's offering is. How does it work?

Tome is a visual storytelling tool for work. It uses live data, a system of drag and drop tiles, and now AI to help you weave a compelling narrative together. A Tome can be as visually interesting and impactful as a high fidelity video, but also as easy to build as a document. A lot of people use it for presentations, and since we've launched recently, we've seen people use it for other things as well, like websites or portfolios or quick idea sharing. I feel we could have only built a product like this by leaning really heavily on the systems thinking and interaction design skills of our product design team.

How does design really play into the core of a company's product offering?

If a product has a touch point with an end user, then there's a way to be intentional about how that experience ends up working. And I think design at its core is just the definition of that process. So like thinking through, even if the only touch point is a website, just thinking through, you know, the mental state someone is in when they get to that website and what they, you know, might want to, might want to see to compel them into the next step and organizing the information they encounter and process and kind of walking them through that. And if your product is something that's like really engaging or requires a lot of interaction, that's, that's even more surface area for someone to think through, really intentionally. So when we think about what is a designer doing, you know, to fit into a company's core product offering, it's, it's just kind of bringing a bunch of considerations into an intentional thought process of how someone experiences and interacts with the company and its product.

That's really helpful context. Now I want to get to Katie. You work with a wide range of startups in the Greylock portfolio and you help them find and recruit some of their earliest employees. And I know lately you've been getting a lot of questions from founders about the design role they figured out. It's really clear that they need to think about it at the initial stages, but a lot of them are still not really prepared to go about hiring this role. So how do you help them understand how to begin the search?

So a lot of it is just educating. Very few founders are like Henry and have design experience and they aren't really prepared for how hard it can be to find that first designer. As we just heard, it's not nice to have afterthought anymore. But a crucial part of how Customers interact with your company. And we all know that a bad UI design can deliver misunderstandings. It can also bring a sense of confusion and frustration to the customer. And so it's really important for founders to remember that the first designer is usually the only voice for design at this stage. If they don't uphold the quality of design, no one else will. And then there's the timing of it all. One thing that comes up is founders aren't always aware of how critical it is to get someone in early. And when people wait too long to bring in a designer, they're setting themselves up for a very painful recruiting process. At the most basic level, very few designers will want to join a company that doesn't already have some sort of design function in place because they'll have to spend most of their energy trying to convince people of the importance of the design and why it should matter, rather than doing great work that advances the mission. And that's a really frustrating place for anyone to be. And then you get into this classic hiring mess, you start getting desperate. You think about hiring someone who isn't a good fit, maybe you bring in someone who's too early in their career. And so one thing that could be interesting to explore and something that I do recommend to the founders, you know, when we kick off the search and while they're looking for that perfect candidate, is to think about leveraging a design consultant, you know, someone that can come in and really help bridge the gap between design and the product teams from the very beginning.

Right. And as you're talking, I'm thinking, you know, what does this person actually look like? What does their skillset look like? What are their primary skills?

I mean, I think even starting with a consultant is better than nothing. Just from the perspective that someone is there again, thinking kind of intentionally about like, you know, what systems need to be put into place and what are like sort of the core problems here. And so, you know, someone can at least start to put together the beginnings of a design system or the beginnings of like a mental model for how to build out the product. And you can find ways to systematize those things. And you want someone who can come in whether they're, you're not consultant or an actual first full time hire and think through that that way and lay that foundation. In addition to the like, you know, very apt point that you made, Katie, about most designers wanting to spend more of their time exploring and pushing the mission through their work rather than advocating for their ability to contribute at all. I think another component of that is that someone has kind of come in with a starting point that can really kind of extend out into different directions. Just as an example with Tome, we spent a lot of time on this sort of horizontal layer of the product that created lots of space for people to come in and vertically work on individual features. And I think early on that kind of pattern might seem really familiar from an engineering perspective, but it's not often thought about too much in the same light in the context of design. But it totally applies too. And thinking more a little bit about how we want this person to be shaped, I can't emphasize that systems thinking component enough because you're making so many different decisions that you need this rhyme or reason sort of continuing through all of them. And to be able to recognize the patterns of decisions you're making and try to orient them towards being better ones is sort of what the systems thinker can bring to the table. On top of that, of course, everyone at this stage has to be pretty scrappy, has to be okay with building things and then tearing them down overnight. I think the sort of newer thing in the past, I don't know, five, 10 years in this field has been the importance of prototyping and being able to put living, breathing experiences into people's hands so that you can viscerally feel how an experience, you know, would kind of come out to an end user. So I think those are like really kind of important ingredients. And then maybe the last like sort of soft point here would be someone with enough kind of independence or confidence in themselves to be able to disagree with you. Especially if you're a founder, right? You bring in someone that is there to, you know, kind of lay this foundation of design thinking and help you translate your vision into a visual kind of graspable thing. You're going to want that person to have, you know, a lot of agency and a lot of room to play with for themselves and you want to kind of let them disagree with you as well.

And as far as when you're evaluating someone's portfolio, how is this demonstrated?

We kind of think about this across a few primary skills, just like visual design, like color type, layout, interaction design, animating and interpolating between states, and problem solving, which is having like a human problem in mind that's pretty relatable that you've scoped out and being able to stay close to that as you come up with solutions. We like to look at those hard skills and you can kind of pretty easily see the visual interaction design stuff come out of the top layer of a presentation or a portfolio that someone might send you. You know, as you're evaluating that depending on your kind of level of familiarity as an individual, you might like, compare it to other experiences that you've felt really great using. Maybe if you really enjoy how it feels to interact with apps on your phone and you kind of play with or look at the designs that this person is sharing on their portfolio, you might think about how you feel in reaction to that. I think that that often can be a reasonable substitute for really understanding what the depths of their execution skills look like.

I would just add to that. And this is true of any role at any company in its early stages. An early designer needs to have humility. They have to have the ability to collaborate and take constructive feedback on their design work and that should be something you can really suss out in interviews. And also they need to have an autonomy and ownership mindset and have self confidence in their design skills and they should be able to communicate this to product teams. So in the past they may have relied on their manager to convince people that their design is impact, but now they need to be the one doing the convincing.

And I think especially at these early stages, you know, you might find characters out there that really spike in one area and are world class at that. But I think what you might be looking for in a startup context is someone that is again, scrappy and also well rounded. I mean, you really will benefit from this person being able to speak the same language as engineering and for them to be able to lead their own endeavors to fruition. Just as an example, at tome, we went quite a While without a PM, almost like 18 months into our product roadmap and even now we only have 1pm and 4 full time product designers. The designers are often able to fully articulate the end state of the product they want to build through an interactive prototype and then spec out in detail how engineering should think about building it and then that becomes really tight collaboration. So I mean, for us, you know, our designers ability to interface really closely and productively with engineering has been, you know, an irreplaceable component of our process. It's worth calling out just because I think so much of the time designers and engineers are kind of like kind of sitting quite far apart. And there's this phenomenon you hear about sometimes where, you know, there's a spec being thrown over the fence and then someone kind of takes it and builds it and then there's this inefficient feedback loop of it being not quite what the designer may have wanted, and then there's a back and forth that happens and you don't really have time for that in a startup. I think you want to just kind of be in the smallest feedback loops possible between all the people building.

Yeah, absolutely. And I want to hear more about how you were able to build up the design team with the product teams at tome. But let's back up a little bit and Katie, talk about how you, you actually help these founders think about recruiting. I mean, they're very early stage people. Each role that they're looking for is different. But having that system in place to even begin their search, how do you advise them there?

So when I start working with hiring partners, I always advise them not to wait too long to start recruiting for a designer. If you know you need someone eight months from now, start looking today because it can take several months to land that higher and you can run the risk of slowing down on product launches. Definitely tap your own network, whether that's people you used to work with, advisors and even leverage your investor network. And one thing I'm always happy to do with our founders is become like structured talent hunts because I often find that we know more people than we realize by simply going through first connections. And then the best way to start the process is with the same approach you would use for any role you're trying to recruit for. Starting with what are the strengths of your team now and what do you need to hire for? And so the first thing you'll want to do is just identify the role of a designer on your team. You know, are you looking for an end to end designer, but someone who has a strength in one particular area, you know, is domain knowledge critical to the success of the role? You'll want to think about what strengths would make them successful at your company. So for instance, is someone who can come up with a general design strategy and then execute important for your team? Or maybe you have someone who's strong in this area and you mainly need someone who can take the team's vision and put it into a hi fi product mockup. So these are all things you'll want to think through and then find a thoughtful way to interview them to identify those strengths.

Right. And once they figure out what they're looking for, then comes the really hard part of finding these people and then evaluating them. And maybe this would be helpful if Henry, you could tell us how you went about this at tome. What did it look like as you were building up the team as far.

As like, you Know, breaking this down into sort of sourcing and evaluating for sourcing, it really makes sense to look at other companies if you're kind of doing it from scratch, looking at other companies that are building things that you think are similar to what you might need, you know. So for example, if you're building like something that's very interactive and very, I don't know, communication heavy, you might look at like, you know, popular consumer apps. You might look at, you know, products that have kind of required the sort of craftsmanship or, or thinking that, that you see as an end user in them already. And like, look at companies like that and just see, you know, if anything's kind of going on, if folks are in the middle of a transition. And one thing that I kind of learned that was pretty counterintuitive, at least to me, was that we're kind of like a, like a tool for work, right? And there aren't a lot of people that are, you know, working already at a tool for work company that want to join your slightly different tool for work company. But there are, are, let's say like in the consumer product world working on like social, for example, but do want to find a way to like, apply what they've learned to a different context. And so the interesting key there was like finding folks that have a skill or something to bring to the table that will really help you in your mission. But there's like so much also for them to grow and kind of bite into that's unknown about what you're doing. That kind of helped us like find folks that could really learn and kind of bring something new to the table rather than only finding folks and cycling through a lot of the same people in the same industries. You know, tome is a heavily visual and interaction design dependent product because at the end of the day, what you're getting as an end user is something that is largely designed for you. And the process of putting a tome together is so kind of interaction heavy that the ability to think through all the different states, you know, that you might encounter and how that all feels while you're both thinking and populating content in the canvas. I think all of that really puts a heavy strain on those hard skills that I mentioned around visual design, interaction design and systems thinking. So when we put our team together initially I was just doing a lot of the design work myself, but the quality bar, given the breadth of the surface area was quite low. I would say what was happening as we brought on each individual incremental designers that they could kind of Take a piece or, you know, a large area even and really develop that far more deeply just because they could focus on it and they could think about, you know, how to improve like the most important parts of it over time. We kind of built a team that had different strengths. I think about them kind of like a basketball team, almost like they're playing different positions and they, you know, all can cover a lot of the same bases, but do their individual sort of special strength in a uniquely great way. So we have someone on the team that's like super specialized in interaction design and like prototypes, their own like live code versions of the product even to kind of visualize like where we want to go and give people links to that. And I just don't think we'd be anywhere close to where we are as a product if they weren't kind of off exploring these like, kind of alternate realities for the product and then sharing it every week with the broader engineering team and giving people links to these sort of interactive repos that they've built to kind of show us what the product could be if we built what they were thinking.

Do you ever get inspiration for the product from interesting use cases that you didn't anticipate?

Yeah, totally. And interestingly enough, like a lot of the use cases that we're seeing emerge right now are coming from like the product design community too. You know, a lot of like interviewing for a company, you know, folks kind of lean on tome for, because you can really quickly put something together and it doesn't feel like you've invested a ton of one off energy for this conversation with a potential employer that might want to see a permutation of your portfolio. And yeah, I mean, we kind of use our own team and like the community around us and folks using us as like a sounding board to try these ideas with. And whenever it feels like the product has become kind of good enough to like meet the personal bar for like a designer on our team sharing their work or for someone in the community doing the same, it feels like a kind of milestone in the right direction. It feels like we're able to kind of let someone do their best work in an area and that in turn, like, you know, the feedback we get from that really comes back and shapes the product.

Great. You're talking about all the things that you're doing right. So let's talk a little bit about maybe things that people might do wrong. Like aside from waiting too long, which you said, like, what are some other mistakes that you've seen teams make during the candidate search process.

It's hard to imagine a world where you can start a design practice at a company without someone that is really close to the founders and really experienced themselves. And I think that you can kind of handle that a bunch of different ways. But at the end of the day, you need to be able to develop this deep relationship with this person, which is probably why the timeliness of it matters so much. It'll probably be hard to develop that relationship, you know, 50 people in, you know, compared to much earlier on. And then, you know, you have like someone that is kind of positioned as a translator almost between say the founders or the founding team and anyone new brought on to work on the design that can like turn that intent into actionable sort of language and have a say in how it continues to evolve from there. And like we talked about before, I think they really have to have their own principles that you believe are going to lead your product in the right direction for your mission. And that's, that's, I think what this ends up coming down to. A lot of the time you probably won't be able to find that person for cheap for just being honest here. I think that you probably need to, you know, really carve out some space in like your option pool or whatever your, you know, however you're handling this for that person to come in and really set the bar for them to have this impact in the first place. And I think you might be surprised in some cases at how great of a long term relationship that can set you up for.

And have you ever heard of candidates deciding not to go with a company just because of the way in which they were being interviewed or the initial projects that they gave them.

There was this whole take, homework, conversation and it's a really tricky one because you don't really get that much incremental signal out of a take home assignment. And you do sort of create this investment and if that person is great, they probably have more options. And imagine if they had like that number of options times that number of, you know, take home assignments, right. They're probably not going to be able to even put their best foot forward there. So yeah, I think there's a lot about your interview process that signals to a design candidate, like how you're going to do everything as a company once you, once you actually join. Right. Like how thoughtful is this group of people? How far ahead and how like kind of systemic are they and evaluating sort of qualities consistently and you know, what do they ask of people, what kind of relationships do they set up with employees? Are they sort of like a. Do they have a good balance of give and take, or are they like mostly give or mostly take kind of thing? So I think all of those can come through in an interaction like that. And maybe your goal as a, as an interviewer is to tailor your process to, to give you the kind of person that you want, which might vary depending on what you're doing.

Building on that a little bit more, this question's for both of you. It's ultra competitive right now to land founding designers and what are like some of the main selling points that founders can use to leverage their offering to their first designer? Especially, you know, if they're very early stage. It's not proven, you know, everyone's already often concerned about working with a startup in the first place.

Another component of what you might be looking for in this person and a way to pull the right person in is finding like a fit with your problem statement. And like, if you are, let's say, you know, exploring, you know, something like tome, I'll just use that as an example. It's like if you're talking to someone whose eyes light up and they get really excited when they think about, you know, helping people express ideas or like helping people visualize something, and they think about, like, all the stuff that they might enjoy building, like, you know, interactive tools or kind of like modular systems or whatever they think is kind of on the path to that. You're definitely going to want to find someone who's kind of excited to come in at this ground floor and for that type of character. That is a selling point. You know, the fact that, like, no design work has been done and the fact that they'll be able to work with, you know, you as a founder to kind of establish all of this, and that almost ends up being the kind of like raison d' etre for this type of person, right? Is that they get to be the one that establishes this foundation and they can take that experience with them forever wherever they go. They can easily sort of point to this example of their impact in something that hopefully a lot of people are using at the end of the day. So I think a lot of that can be really personally gratifying. And I think with a lot of crafts like product design, many of the, like, best people doing this are doing it because they just get a kick out of building something and enjoying it or enjoying how other people use it. So giving someone that opportunity and really trusting them with it, I think is, is kind of the sell of the work itself.

I mean, those are really good points, Henry. And the only thing I would add to this is make a competitive offer. You want to look at the market data and anchor to a percentage so there's consistency across your teams. But you should also be prepared to go above and beyond for extraordinary talent. The goal with your early team is find and hire A plus talent. They need to be legit. And when you're lucky enough to find them, make sure you give them an offer that's good a exciting putting yourself.

In the candidate's shoes. And Katie, this is a question for you. What kind of questions should they be asking? What should they be thinking about when they're evaluating the company as someone that they would want to work with?

Yeah, this is a really good question, Heather. Honestly, I probably talk about this several times a week to folks that I'm speaking with. They ask this question often. But obviously you'll want to make sure the mission speaks to you. You know, and I always advise talent that they need to make sure they're taking intelligent risks. Sometimes going to an an early stage startup can feel like an irrational thing to do. And so, you know, how do we kind of eliminate the risks? And a few questions that they should be asking themselves is, you know, is the company solving a problem customers care about and do they have a differentiated approach? You know, are people willing to pay money for this? Also, who are the founders and what are they about? What are their backgrounds and track records and do they have strong moral codes? You'll want to research their investors and board members and figure out what their track records are, is their valuation in alignment with their progress and stage? I think that's a really big one right now. And then lastly, the founding team will set the culture for the rest of the company. So I always tell folks, make sure they, they meet as many of the founding team members as possible and make sure they have good values that really resonate with them.

Just to build on that through the interview process and through whatever other touch points you can gather this from. I mean, I think kind of modeling out what you think this company or their leaders, like sort of decision making formulas are is a pretty interesting approach because you're going to be like living through that decision making formula all the time, right? Whether it's like a relationship with like new information and like how that gets handled or like a dependence on quantitative analysis or qualitative analysis and where the biases might be there, you know, often, you know, at this really early stage you're gonna have really imperfect information that you have to make product decisions with. And that makes the kind of formula really important because, you know, you don't have this, like, really clear story painted for you by lots and lots of evidence. And you have to kind of rely on your best guess and your best interpretation of the signals you do have. So figuring out how the founders and the founding team behave with limited information can pretty much dictate how your experience will feel as you're in the trenches building with them. I just want to kind of highlight a point that Katie made earlier around. What are your signs to sort of run for the hills as a designer when you're initially talking to these companies? And I do find that for whatever reason, it ends up being pretty binary in that, you know, either this company has a really successful sort of experience hiring and building a design function, or it's like, really struggling to kind of break through that. And I think that that, like, kind of perception of time spent advocating for the things that matter is definitely a big component. And I think that just the company having figured out, like, what it wants designed to do with that company is another big component too, for us. We've decided we want design to be at the beginning of, like, every sort of product thought process. And we do like an hour critique every day that sort of manifests that. Even if that sounds like a lot. When I share that with candidates, they kind of get excited. They're like, oh, like, you know, design is sort of figured out maybe at this company, like, there's a way for us to play. And that's. That might be preferable to most people than coming somewhere and nobody really having a clear idea of what you doing your job well looks like. And for that to sort of be on you to define and explain to.

Everyone what about anything that would like they would be okay for other roles but wouldn't work for a design role, such as hiring someone who's in another country with a huge time difference or any sort of things like a language barrier or just any other things that we might not think about if it was someone like an engineer or a sales team.

I can talk about the time difference because this comes up often, in my opinion. I'm somewhat against this unless the, you know, the designer or, you know, the person has done this before and has had success. It just. That time difference can be really hard for teams. Even, you know, if you're fast prototyping or trying to iterate on different things. Sometimes you're waiting a day to hear back from folks, and it can just slow things down. Down.

Yeah. I just think your proximity, you know, whether it's, like, physically or mentally to this initial person is really important, you know, So I think being able to speak the same language somehow and ideally be in the same room for lots and lots of time upfront is so key. It might even be more key for what you're doing than spending that time with engineering or other functions that are really close. Because you're taking that kind of, like, first step from an abstract desire to build something into, like, figuring out what it would look like or how it would manifest in an actual, like, product environment. And that process is so abstract that you want as much time to be able to, like, interact with each other as possible. So I would definitely recommend, you know, finding a way to be in the same room together if possible. If not, just, like, having lots of time on Zoom or whatever you might do to solve it.

Yeah, makes sense for us.

We really wanted design to be both motivated to, like, dream up whatever the, like, kind of best future product realities they can think of were, and to be empowered to kind of, like, go and make them real and also as a result of that, to kind of hold them accountable to making them real. So that kind of creates this, like, incentive loop of, like, well, you know, I should only really prototype and draw the things that I can actually realistically explain to someone who could build them. And I think that as a result, kind of brought design engineering a lot closer together. And what we see now at tome is that, you know, designers will often prototype things and next to kind of code level quality, and then, you know, sit next to an engineer and actually make that happen with almost no gap in terms of expectations of what, you know, the end up, end product ends up being, and, you know, the kind of dirty work or the legwork required to get there is like a, you know, a table with lots of, you know, workflows spelled out in it and, like, milestone planning and like, test planning. And a lot of that stuff isn't a usual part of, you know, a designer's, like, role or responsibility. But I found it to be a pretty compelling sell for people that are looking for an opportunity to really shape a product experience and not kind of be a part of an assembly line process where everyone has sort of a predetermined contribution to a process and everyone's sort of subject to the outcomes of that process. And instead, you know, these people can be sort of the lead actors in some way to kind of make their vision a reality.

That's great because as a result of all that hard work and back and forth, you've created this product that is so easy for someone like me to just pick up and articulate any thoughts or ideas I have with visual storytelling tools without him to think about the things that I wouldn't know how to do otherwise.

Thank you. The team would be really excited to hear that.

Awesome. Yeah. I encourage anybody, any listeners who have not experienced the magic of Tome to check out the website Tome app. Yeah. Excellent storytelling presentation tool for work made by all these brilliant designers and product managers. Well, Henry, Katie, talking with you both has made it. I've learned a ton. I learned a lot about how important design is and how integral it is to the early teams and how crucial it is for a company to get it right at the early stages. So thank you so much for joining me on Gray Matter today.

Thanks, Heather.

Yeah, thanks Heather.

That concludes this episode of Gray Matter. If you like what you hear, please subscribe wherever you get your podcasts and please be sure to leave a five star review and any feedback you may have. You can also find all content on our website, greylock.com, and you can follow us on Twitter reylockvc. I'm Heather Mack. Thanks for listening.