In this episode of 'Never Too Early,' Lauren Ipsen, Talent Partner at Decibel, hosts Sally Carson, an experienced design leader with a background at LinkedIn and Duo Security. Together, they explore the top five questions founders have about building their design organizations from scratch. Key topics include the timing and type of first design hires, the roles of product and brand design, introducing user research, and the benefits of hiring generalists versus specialists. Sally also shares her personal experiences and offers practical advice for effectively growing a design team in a startup environment.
00:00 Introduction to Never Too Early
00:19 Meet Sally Carson: Design Leader Extraordinaire
02:05 Diving into Design: Top Questions Answered
02:22 Question One: How should founders think about their first design hire? Sally and Lauren talk about when the right time to invest in design is and what investing in design looks like in the early days.
06:01 Question Two: How important is seniority for your first design hire? What’s the right level? Lauren talks about her own experience hiring designers and how she struggled to find designers for a startup that successfully balanced strategy and execution. Sally also talks through why it might make sense to avoid marquee names like Meta and Google early on.
09:09 Question Three: Sally discusses how she personally feels that it’s important to invest in product design first, especially before finding PMF. Pouring fire on the brand component and the marketing funnel should come after.
11:02 Question 4: When is the right time to invest in user research? Sally talks about how user research has really moved away from the academic connotation it came with 15 years ago and has become far more pragmatic today. She talks about how the right person in UX can be great to hire sooner rather than later.
14:49 Question 5: Should founders be hiring Specialists early on or Generalists? Sally talks about why she feels it makes sense to introduce specialization later in a company’s growth cycle.
16:59 Sally’s Final Advice for Founders
18:51 Closing Remarks and Contact Information
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Transcript
LAUREN IPSEN: Welcome to Never Too Early, a YouTube series focused on unconventional talent insights for founders. I'm Lauren Ipsen, Talent Partner at Decibel. In each episode, we'll cover the top five commonly asked questions that we get from founders building their organizations for the very first time. It's never too early to learn from the best.
I'm super excited to introduce my guest today, Sally Carson. Sally has led design at LinkedIn and Duo Security. She built duo's product design function from scratch and has led numerous teams through hypergrowth to exit. Sally has also been a founder and is the most qualified person I know to answer the top five commonly asked questions that we get from founders building their design organizations for the very first time. Well, first and foremost, Sally, welcome to the show.
SALLY CARSON: Thanks for having me. I'm excited to chat.
LAUREN IPSEN: Thank you so much for joining. I really appreciate it. So I just went over your incredibly impressive professional background, but it would be amazing if you could share something fun about you on a personal front for the listeners.
SALLY CARSON: Sure. I have, just in the last six months, gotten into bouldering, indoor rock climbing, and that's been a fun thing to have. I'm, people who have known me for a while know I'm a big-time bicycle nerd. I'm a retired New York City bike messenger. I've done long distance bike touring across Thailand and the US. So it's very fun to have a new sport that I'm intensely excited about.
And I'm a newbie. I think it's so healthy to have something new that you're not good at. It's like literally and figuratively flexing new muscles for me. So it's just been so fun, really fun to have a new sport.
LAUREN IPSEN: I'll give it a whirl. I'll come join you.
SALLY CARSON: Let's go climb. It's so fun. I'm always happy to climb with other folks. It's very social. Yeah.
LAUREN IPSEN: I've tried once or twice, and yeah, I always think that it always looks easier than it ends up being, right?
SALLY CARSON: I'll make it look hard.
LAUREN IPSEN: Okay. Okay.
SALLY CARSON: Does that help? I'll be like, can't do it. And then you'll be like— LAUREN IPSEN: You and I together will make it look realistic.
SALLY CARSON: Real difficult. Yeah.
LAUREN IPSEN: Cool. Awesome. That's a fun one. Okay.
So today you and I are going to cover all things design, and we're specifically going to focus on the five most commonly asked questions that I get from founders building their design works for the very first time.
So we're going to jump into it, if it sounds like a good plan to you. SALLY CARSON: That sounds great.
LAUREN IPSEN: First and foremost, question number one. How should founders think about their first design hire, and when is the right time to start thinking about that?
SALLY CARSON: Yeah, that's great. And I'll be speaking in generalizations. I'm assuming these are VC-backed startup founders. I think, if we're thinking about hiring a full-time person, there's a lot of considerations, right? I'm a former VC-backed founder. So I have raised money. I have made hires with VC money.
So you need to think about runway and burn rate and all these things. And how technical is your product? You know, how much of that investment needs to go into data science or engineering? So I think that when you're iterating towards product-market fit, to some degree, you can get away with working with contract designers sometimes, if it's the right person.
And I would encourage folks to make sure, if that's the case, make sure you're working with a designer who, their subspecialty is startup, like zero to one, because that is like a particular unique specialization within the broader term of product design.
When you're ready to make your first design hire, I think you should focus on product design first in those early stages because you're bringing a first product to market. You're trying to iterate towards MVP. You're trying to iterate towards product-market fit. So really hiring beyond that specialization of zero to one startup designer, you really do want to hire a generalist, someone that can help you with user research. Someone strong in prototyping because that'll actually help save on ENG cost. So someone who can help with concept validation without having to fully code something is helpful.
There's a lot of smoke and mirrors that designers can do with highly complex functional prototypes in order to put them in front of target customers and see how they're resonating or not. So very much looking at these things through that lean startup, lean UX kind of lens of, like, what's the minimum we can do in order to test our hypotheses early on and kind of derisk some of our assumptions.
So that product design generalist that's skilled in some amount of just kind of guerrilla user research, prototyping, iterating towards, you know, vetting concepts is very helpful in the early stage.
I would say don't go straight into hiring your head of design executive person quite yet. It's a little early for that. So focus on the IC, and hopefully someone who's like, I would say senior level IC, because you do want some professional maturity.
You know, if you're hiring a junior designer, it's like, one way that's helpful to think about it is as a designer is moving through their career and progressing from junior to mid-level to senior, generally speaking, they're moving also from kind of surface level polish towards something that's more strategic. And the more senior a designer starts to become and the more that they're incorporating user research, the more they actually start to look sometimes like product managers.
So if you're able to get that sweet spot of a skilled, experienced, professionally mature senior IC designer, because of the concept validation prototyping they're doing, hopefully they'll reduce your ENG costs, and you'll get more out of your engineers where you need them.
And, in theory, you might be able to even augment your product team with that skilled designer, if they're able to bring some of that user research, the things like competitive analysis and concept validation, things that can really help take some of the burden off the product manager's plate. And hopefully be a very close, trusted partner and peer to your head of product, who might at this point be a CEO, if you're a very early stage startup founder.
LAUREN IPSEN: Yeah, totally. Something that I've found in hiring product designers myself is something that you just kind of spoke to a little bit, which is, there's a really fine balance on the seniority side of things, where you can, as a startup, get the exact type of combination of strategy and execution that you're looking for.
And I have found that I've struggled sometimes, because I've hired folks that were maybe a notch to senior from bigger organizations, like a Meta or like a Google, and they're very used to maybe working on one component of one feature of a product.
SALLY CARSON: Mm-hmm. That's right.
LAUREN IPSEN: And perfecting it.
SALLY CARSON: Yes.
LAUREN IPSEN: And so, when you're in the early days of iterating, and changing things constantly, and pushing things that are far from perfect, it can be a really difficult challenge for them.
SALLY CARSON: Yeah, that’s right.
LAUREN IPSEN: Yeah. I don't want to overgeneralize it, but I guess how would you recommend that our founders vet for the right level and the right type of person?
SALLY CARSON: Don't get tempted by the marquee names like Meta or Google because the environment can be so profoundly different. However, there's some caveats there. Sometimes there's a little incubator team within a larger org that feels more startup-y, right? Or if you sort of found product-market fit, and now it's about just growing the business, maybe at the early stages, finding someone who had been on a growth team, which, within a larger-scale enterprise, could be interesting.
And what I like about that specific specialization early on is those designers tend to have the muscle of being very metrics-informed. So the Build, Measure, Learn cycle that we want to see in early stage startups, ‘cause it's all about testing hypotheses, derisking assumptions. It's very experimental. Growth designers have that fluency. They have that language. They have that approach, as opposed to maybe the archetype you're describing is the designer who, they might get three quarters to work on one initiative, really polish it, they're really into fit and finish.
And if that's the archetype you end up accidentally hiring because their portfolio probably looks very polished and their marquee names are very impressive, you might find that designer is capable of shipping really high quality work, but they're chronically frustrated with the environment, right? Because everything, all their work's getting thrown out. They're trying to collect portfolio pieces for themselves. They have nothing to show, nothing to show for the time they spent at your company.
And this is why I encourage startup founders to hire that designer that is self-purported to be zero to one. So that's even something you might see in their LinkedIn headline, or if you kind of look at their experience, you've seen this. There's some designers that—there's that archetype that just loves that stage, that, like, how do we iterate towards MVP? How do we iterate towards product-market fit? That's really where they've grown their depth and breadth of experience. And it lights them up, that type of dynamic and that type of work. They really, really like it.
LAUREN IPSEN: Yeah, cool. Switching gears a little bit. Talk to me about the role of product-market fit in the decision-making process, on whether to invest in product design or brand design first.
SALLY CARSON: Yeah, that's great. I would encourage—I kind of hinted at this earlier. I would encourage startup founders to invest in product design first. And the reason being, it's like, we don't want to pour too much fuel into the marketing machine until the product is actually resonating with our target customer.
So early, early days, we are iterating collectively and collaboratively cross-functionally. We're iterating towards that product-market fit and seeing what resonates. And there's going to be a lot of pivoting along the way. That's sort of inevitable.
And once it's resonating and you have product-market fit, then—then it's like you're kind of pouring the gasoline on the marketing machine to try to fill the funnel and get more leads and all of these things. Then this is the moment where the brand is becoming more important.
I think if you invest in brand too—I think it's tempting, honestly, for founders to invest in brand. And I think I even made that mistake myself as a founder, despite the fact that I was a designer, because it's kind of fun. You know, you're like, we need a logo and a cute name and a website.
And there's some amount of that that you need, but really investing it and perfecting it—if you've done pretty significant pivots along the way towards product-market fit, the way you ultimately position it in market could change quite a lot as well. You might even find that it's resonating with an entirely different audience than you initially suspected. And that's going to have ramifications for the brand, right?
So I would hate to see founders invest prematurely in brands before they found product- market fit. I think if they have to choose one or the other, product design is the more worthwhile investment. That's time or money well-spent. And it's going to be necessary as you're continuing to iterate.
LAUREN IPSEN: So when is the right time, then, to integrate more user research into the development process?
SALLY CARSON: Yeah.
LAUREN IPSEN: And how can it really benefit the portfolio—or the company more generally?
SALLY CARSON: Yeah. You know, at Duo, I invested in user research very early. I want to say my second hire—first, I hired a product designer. And they brought me on maybe, like, series B. They brought me on as a head of design to build out the org specifically, as we were just about to start entering hypergrowth.
So maybe Duo was about a hundred people. And over the next few years, we'd go to a thousand. And first I hired a product designer, more junior. And I think the next hire, if I'm remembering correctly, was a user researcher. And the reason I did that was because so much of the product we were building had to do with just people's fundamental relationship with technology.
It's a two-factor authentication app. So it's a B2B and a B2B2C. So we're designing for the consumer experience, but we're also designing for the enterprise. And in order to—and, you know, it's like, there's this compliance piece. Like, are people actually using 2FA? Are they just dumbly mashing the accept button in a way that's kind of scary? And if so, why?
So understanding all of the behaviors around password management, passwords, anything around just security hygiene, I don't like the term, but general hygiene around your behaviors with security. We wanted to understand that at the consumer level, because that was going to inform all these product decisions that we were making. And I personally had this belief that if you make that end user successful, that in turn makes that IT manager successful, that admin.
So there was early rationale there. I suspect it's the case that a lot of startup founders don't have that same rationale. A lot of folks now are building purely B2B. There's not a B2B2C type of play. So it might be less critical in the very early stages.
However, just like, if you're able to hire a designer that's more senior and they are helping to augment and support your product team, the same can be true for user research. So if you're finding that maybe your product team is underwater, and—but you're not quite at the point where you're ready to hire another product manager, it can be very helpful to have a user researcher there because they can take a lot off of those product manager plates and partner really closely with them.
I would say, I think, generally speaking, second hire for the design team, I probably wouldn't advise that. Depending on your ratios and how many engineers you have and things like that, I would want to keep the engineer to design ratio healthy before introducing user research.
But you can work with contract user researchers as well and get a lot of that, get a lot of bang for your buck out of that. I think it's incredibly helpful because—and I advise founders too, sometimes user researchers get a bad rap for being—slowing the process down, being overly academic.
I think user research has improved over the years because of that feedback that they've gotten from their cross-functional partners. And, generally, they understand now that what we're looking for is actionable insights, you know? And so the faster that we can be embedded in a cross-functional way, work together quickly, build product.
And the goal of user research is, like, what decisions will we make? What strategic decisions will we make as a result of what we've learned? As opposed to, you know, 15 or 20 years ago, user research had the reputation of, the goal of user research is the 30-page report at the end that maybe no one is going to read.
So I think user research is much more pragmatic now about the speed of the product development process. But again, that's something you could vet people for, is kind of understanding how do they embed with that product development process.
LAUREN IPSEN: Yep. Okay. My final question for you, in the early days, for a startup, should they be hiring for specialists in their domain, or are generalists a better way to go?
SALLY CARSON: Yeah. I would encourage folks to introduce specialization later. I'm trying to think. Maybe at Duo, by the time we had a 15-person team, maybe that's the point at which we started introducing specialization, with the exception of—I think we had a UX engineer that I hired, that started to build on our design systems early on.
And that was to, I mean, one, just make sure that the product experience is really cohesive, and that it's cohesive with the brand experience. Two, to reduce the burden on front end dev. Ultimately, a successful design system is going to reduce your front end dev costs and reduce design costs as well. So there's some efficiency gain there if you start investing in design systems.
Aside from that, so we invested in user research early, design systems early. But I would say, depending on the nature of the startup, your first few hires just being very generalist product designers, I think is a decent way to go, particularly because many generalist product designers that are more senior, they will come with some amount of user research experience.
They might even—some designers, love building out design systems. So you might—there's a lot of things that you can kind of get naturally by way of hiring a generalist because they will have their own interest that they tend to gravitate towards. So some of them might like to do some user research, and that will come through in the interviewing.
Some of them will have a natural interest in design systems, but they don't want to pigeonhole themselves completely there. So they like to build an MVP of the design system, but then ultimately hand it off to that person who's more the long-term architect of the system. So there's still quite a lot that you can get done in terms of laying the foundation for a healthy design org in the future just by hiring generalists.
LAUREN IPSEN: Awesome. This has all been so helpful. I can't thank you enough. I think that our founders are going to find all of this incredibly insightful. Any parting pieces of advice, words of wisdom to our founders that are building design orgs for the first time? Learnings?
SALLY CARSON: I coach leaders, so I'm always encouraging folks to be super honest when you're making a hire. Let's say it's the first design hire, and you're hiring a senior IC. I would just be very honest about, this is not a head of design hire. You might be reporting directly to head of product or even to the CEO.
Be honest about where they will be in the org. Be honest about how that might look different in another six months or 18 months. So the plan might be, like, there's a lot of variables here. It depends on funding and things like that, but it's possible we will hire a head of design in another year and that will be your new boss.
I think just generally, for leaders, share what you know when you can. Be honest. Be honest about what you don't know. It really helps establish trust. And because our work is highly collaborative, relationships and trust is—that's the foundation for everything that we do. And so just being clear about, this is what we know, this is what we don't know; about how your role may or may not change in the future as the company continues to grow, I think that's healthy.
Because some senior ICs might say, I'm the founding designer. I'm ostensibly the head of design. But if you haven't had a clear communication about it, they're going to feel really discouraged when you hire that head of design over them.
LAUREN IPSEN: Totally. And the head of design that might come in at series B, series C, could very well be more of a people manager and someone that can help with systems and process way more than the founding designer, who is probably deep in Figma and hopefully thinking about more of the creative vision.
So it can be two very different roles also. SALLY CARSON: Yeah, that's right.
LAUREN IPSEN: Cool. Okay. Well, I want to thank you again for hopping on Never Too Early.
SALLY CARSON: Yeah. Thank you.
LAUREN IPSEN: This has been great, Sally. I appreciate you so much. And also, for what it's worth, Sally is an advisor to some of our portfolio companies and has done a tremendous job. So if you're looking for someone to bounce some ideas off of, or just want to get her take on all things design, can catch you on LinkedIn. Is that the best way to do it?
SALLY CARSON: That's the best way. Yeah, find me there.
LAUREN IPSEN: Awesome. Okay. Cool. Thank you so much for tuning in to Never Too Early. More to come soon.
SALLY CARSON: Thanks, Lauren.
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