Extraordinary designers

How to hire the rarest breed of founding designers.

Hey there. This is a special essay edition of AI-First Designer to help designers transition into successful modern builders. Members get access to proven strategies, frameworks, and playbooks.

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For those who care about making wonderful things for each other and elevating human experiences through design. Or will, one day.

Felix Lee, CEO at ADPList

Dear readers,

This essay took me six months to reflect on and write.

But I think it’s worth it, very close to heart - what I wish someone had told me earlier, both as a founder and a designer.

Read on.

After startups raise their first round, one of their first hire is usually a founding designer. It turns out this is also one of the hardest to get right, and it has consequences if founders get it wrong. In a world where software is commoditized, good taste will be the differentiator, and much of taste comes from the first designer you hire.

If you don’t hire your first designer well, you will not have a great outcome in product when you’re ready to grow. There is probably no way any good startups can run long without a good designer in 2025 onward. It’s easy to delude yourself that a founder has the best taste, but that doesn’t often scale.

In this essay, you’ll get deep insight into:

1. When to hire

2. What you’re looking for

3. How to evaluate portfolios

4. How to interview designers

5. Bad design hires

6. Common mistakes working with designers

Here are honest, hard-won lessons on hiring founding designers:

*When to hire

Earlier than you think, but later than most designers tell you. The common wisdom I argue against is “get a designer before PMF.” This is wrong. The uncommon wisdom is “you don’t need design at all, look at Craigslist.” This is also wrong in 2025, but less wrong than you’d expect.

Is there a right time? Yes, it falls between having early traction and the experience itself becoming the bottleneck to growth. In a case like: strong retention, but weak onboarding, is churning out many leads. The best way to think of it is: when you have users who want to do a thing in your product, and what you’ve built is preventing them from succeeding at scale.

But don’t be tempted to hire just because the interface looks ugly or users complain about accessibility (unless you’re in this market).

If you’re pre-PMF and spending time on design hiring, you’re wasting precious time. If you’re not a designer, my advice is to take help from designer friends, but don’t make it a formal hire yet. Most founding teams waste time hiring a designer at 3 months when they should be hiring one at 6 months.

The forcing function should be: “We understand what users need to accomplish, we have evidence they want to accomplish it in our product, and our current design makes this harder than it should be in measurable ways.” If you can’t articulate this, you’re too early.

One exception: if your product is fundamentally a design product (design tool, creative software, consumer social), you need design as a first hire. You already know this. If you’re reading this section, wondering if you’re the exception, you’re not.

*What you’re looking for

This is probably the biggest question my founder friends ask me.

You’re looking for someone who thinks like a product person but crafts the details like a designer. This is way rarer than you think.

The profile you want is: opinionated about problems, highly in tune with users (intuition and data), high craft, high product sense, and thinks about business. A fair warning, often most good designers miss the last part. Your first designer needs to have the confidence to ignore just product visuals, but the judgment to know what’s MVP and what’s premature optimization.

Here’s the parallel to software engineer: you wouldn’t hire a Google SRE to be your first infra hire. They’re great at operating mature systems at a massive scale, but they’ll over-engineer everything and move too slowly. You want someone who’s built 0-1 before, probably at a startup, definitely not someone whose entire career has been at FAANG.

“The most common error of a smart engineer is to optimize a thing that should not exist.” - Elon Musk. I’d argue the same for designers.

Red flags that founders miss: someone who talks a lot about process, design systems, research operations, or team rituals. That’s all important at scale. Right now, you need someone who can look at a problem, prototype a solution in a day, test it with 5 users, and ship the winner by the end of the week. Process people are hire #3 or #4, not hire #1.

Green flags you should look for: They ask about your metrics. They want to understand your business model before they look at your product. They’ve shipped products that real people use, even if those products are dead now. They have strong opinions about design patterns, but change their mind when shown data. They can vibe code, at least a little, to prototype.

The best designers I’ve seen are people who share the same trait as great product managers. They understand business context, they prioritize ruthlessly, and they have taste. The worst founding designers are people who want to make beautiful things and think user research means asking their friends (yes, this really happens…).

You want someone who says, “I looked at your signup flow and 60% of users drop off at step 3, here’s why,” not “I have some ideas to make the homepage more engaging.”

*Generalist vs specialist

You will need a generalist.

Your first designer needs to do product design, visual design, basic user research, write copy, make the icons, vibe code a little, and probably build the design system later. They need to own the entire experience from positioning to pixels. If they can’t do all of this at a baseline level of competence, they’re not your first design hire.

Most importantly, they must be good enough at all of it as a foundation to be dangerous enough. The classic example of this was when I branded and designed Gotrade (YC S19) “Robinhood of Southeast Asia” entirely as the first designer. Another good friend, Hannah Ahn, did the same for Superpower (raised $34M).

The specialist trap is appealing to startups because it mirrors how you think about engineers. You hire a backend engineer, then a frontend engineer. But engineering tasks are more separable than design tasks. A designer who only does “product design” but can’t make things look good is like a backend engineer who writes great algorithms but doesn’t understand databases.

It’s not actually a complete skill set and certainly not what you want in a startup.

Here’s the test: ask candidates what they can’t do. If they say, “I’m not great at visual design” or “I prefer to work with a researcher,” they’re a specialist. If they say, “I haven’t done much motion design, but I can learn it,” or “I’m not an illustrator, but I can create a visual system,” they’re a generalist. You want the second type.

The one specialist you might hire first is a product designer who’s exceptional at thinking through complex interaction problems and decent at visual design. They should be embarrassed to ship something ugly, but willing to do it anyway.

Do not hire a visual designer first. Do not hire a UX researcher first. Do not hire someone who “focuses on strategy.” These are critical skills, but they’re supporting skills for a team of 3-10 designers, not the founding skill set.

Also: be suspicious of designers who describe themselves as “full-stack designers.” This is usually someone who learned Webflow, not someone who can design a complex SaaS application. Generalist means breadth of design skills, not that they can also write production code.

*How to evaluate portfolios

This is where founders panic because they think they can’t evaluate design. Most founders can; they’re just asking the wrong questions.

First, ignore aesthetics entirely - that’s your bare requirement. If you don’t like the aesthetics, just move on. But what you’re evaluating is thinking, not styling.

Here’s the framework: look at each project and ask yourself, “What problem were they solving, how do I know if they solved it, and what were the results?” If you can’t answer this from the portfolio, they’re not showing their thinking. Good portfolios tell you the problem, the constraints, the solution, and the outcome. If it’s just pretty screenshots with paragraphs about their “design process,” skip to the next candidate.

Look for someone who shows their work. Can you see the evolution from bad idea to good idea? Do they show the things they tried that didn’t work? Do they explain why they made specific decisions? They should be able to articulate these if they owned it clearly.

Specific things to look for:

Evidence of product thinking. Do they mention business metrics? Do they talk about technical constraints? Do they explain why they didn’t pursue certain directions?

They look at details. Pick one project and zoom in on the details. How do they handle empty states? What happens when an error occurs? These are tells. Anyone can design the happy path. Great designers obsess over the edge cases.

They have range. They should have solved different types of problems—not just mobile apps, not just web apps, not just dashboards. If everything looks the same, they have one solution they apply to every problem.

Real products that shipped. Be skeptical of everything that’s a concept or a case study for a company they didn’t work at. You want to see things that actual users have used. It’s fine if the product failed, but it should have been real.

Here’s the part founders get wrong: you think you should look for portfolios that match your aesthetic. This is like hiring an engineer because they use the same code editor as you. What matters is whether they can think through complex problems with good principles and make good tradeoffs under constraints. The visual style then comes next.

If you’re looking at a portfolio and thinking, “I don’t know if this is good,” ask yourself: “Can I understand why they made these decisions? Do the decisions seem rational given the problem they described?” Most of the time, you’ll realize you can evaluate this just fine.

*How to interview

Please don’t ask them to redesign your product in the interview; they have no context, and it will unlikely yield any exceptional results – it selects for the wrong skills and designers hate it, too.

Here’s what actually works:

The portfolio deep-dive. Pick one project and go extremely deep. “Walk me through how you decided to solve this problem. What were the alternatives? Why did you reject them? How did you know this was working? If you could do it again, what would you change?” Spend 30-45 minutes on a single project. You’re evaluating their ability to think systematically, make tradeoffs, and learn from outcomes.

You’re not judging whether their solution is the one you would have built. You’re judging whether they can articulate their reasoning, whether they considered alternatives, and whether they understand tradeoffs.

The constraints question. “Tell me about a time you had to ship something that wasn’t as good as you wanted because of constraints. What did you cut and why?” This tells you everything. Bad designers blame constraints. Good designers work within them and know exactly what tradeoff they made.

The metrics question (critical). “How do you know if your design is successful?” If they talk about user satisfaction or qualitative feedback, that’s a yellow flag. If they talk about specific metrics (conversion rates, retention, or revenue growth), that’s a green flag. You want a designer who thinks in growth outcomes in the early days.

I further elaborate on what the most important metrics early design hires should measure. You can read the full thread here.

The product question. “Spend 10 minutes using our product and tell me the three biggest problems you see.” This isn’t about whether they identify the same problems you know about. It’s about whether they can quickly build a mental model of what you’re trying to do and identify gaps between intent and execution. Good designers will ask clarifying questions about your users and your business model. Bad designers will tell you your visuals are wrong.

The technical question. “What’s the most technically complex project you’ve worked on? What made it complex? How did you work with engineering?” You’re looking for someone who understands technical constraints and doesn’t treat engineering as an implementation detail. If they can’t articulate what was technically hard about any of their projects, they probably don’t think about technical constraints at all.

I can confidently say that all great designers who worked in startups have had some form of technical constraints; it’s important to understand how they dealt with it.

The taste/judgement question. “What’s a popular product with great design? What’s a popular product with terrible design? Why?” This tells you about their taste and their ability to separate business success from design quality.

Do not ask brain teasers. Do not ask them to critique your favorite app. Do not ask them what kind of tree they would be. These tell you nothing.

The final question you should always ask: “Why do you want to work on this problem?” Their answer should focus on the problem space and mission, not on your company. The best designers are problem-driven. They want to work on climate or dev tools because they care about that domain. If they just want to work at a startup, any startup, they’re probably not going to stick around.

*Bad design hires

While I write about who you’d want to hire, here’s also a list of bad first designer hires you’d want to look out for generally.

Hiring someone from big tech because they worked on a product you admire. This is the most expensive mistake founders make. That designer at Meta who worked on Instagram they were one of 40 designers on that product. They implemented someone else’s vision within an established system. They’ve never had to build 0-1. They’ll expect a level of process, support, and resources you don’t have.

A rule of thumb is to hire someone who’s been the first or second designer at a startup before.

Caring too much about visual. Your product doesn’t need to look like Linear. Linear looks like Linear because they’ve spent years on polish and hired world-class visual designers. Your product needs to be clear, usable, and solve the problem to deliver outsize value. Pretty comes later. If a candidate’s portfolio is all style and no substance, they’re optimizing for the wrong thing at your stage.

Slow speed to production. Lots of designers are great at thinking and terrible at fast, high-quality execution. Ask them: “What’s your typical timeline from ideation to complete design handoff?” If they say anything longer than 2 weeks for most projects, they’re too slow for you. Early-stage startups need people who can iterate in days.

Hiring someone who needs a lot of direction. Your first designer needs to be extremely self-directed because you don’t know how to direct them. If they’re asking you what to work on next or waiting for you to review things, you’ve hired wrongly; fire them fast. You need someone who will come to Monday’s standup and say, “I identified these three problems, here’s what I’m prioritizing and why.”

The inverse trap. “Design is subjective so I can’t evaluate it.” Design is never subjective, art is. Good design measurably improves outcomes. It reduces support burden. It increases conversion. It makes complex things simple. Design is about solving problems under constraints and doing it elegantly.

Hiring too early and hiring too late. You’ll hire too early because other founders/X told you to. You’ll hire too late because you don’t think it’s important. The right time is when your interface is measurably preventing growth. Not when it’s ugly. When it’s preventing users from doing what they need to do.

*Common mistakes to avoid

Not involving them in product decisions. The biggest mistake post-hire: treating your designer as a contractor who makes things look good. Your first designer should be in every product conversation, every user interview, every roadmap discussion. They should have opinions about what you build, not just how it looks. If you find yourself saying “just design what I specced,” likely, you’ve hired the wrong person or you’re using them wrong.

Expecting them to understand your business without explanation. You need to teach them everything you know about your users, your market, your business model, your technical constraints. The best designers ask questions constantly. If they’re not asking questions, they’re either genius (even geniuses ask questions) or they’re just executing without thinking. It’s usually the latter.

A final note on compensation: don’t lowball your first designer. The market rate for a senior product designer at a startup is $140-200k base plus meaningful equity (0.5-1.5% at seed stage). If you’re paying less than this, you’re hiring someone who couldn’t get a market-rate offer. There are exceptions, but they’re rare. Design talent is as expensive as engineering talent. Budget accordingly.

The best first design hires I’ve seen came from founders who treated design hiring like they treat engineering hiring: rigorously, with clear evaluation criteria and high standards. You can evaluate design. You just need to evaluate the right things. Focus on thinking, not aesthetics. Focus on outcomes, not process. Focus on solving your actual problems.

Founders still tend to undervalue design until it’s too late, then overvalue it and hire the wrong person. Hire when you need it, hire a generalist who can ship, increase their quality of thinking rather than only style, and treat them as a core product partner.

I hope you get your first design hire right.

Thank you to Almas Sapar, Zeth Lee, Gerald Chan, Hannah Ahn and Alexis Wynn for helping read the draft.

If you find this essay useful, please give this by sharing it forward — with your thoughts too. 🔄 I’m sure founders & teams can benefit from hiring extraordinary designers.

Thank you for reading. If you have any questions/comments, you can find me on X and LinkedIn.

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