How to Hire Your First Founding Designer (and Not Regret It Later)

A strategic UX thinker? A polished UI designer from a FAANG company? A brand guru with a Behance full of glossy case studies?

Tempting—but probably not what your startup actually needs right now.

What you need is a Founding Designer: a fast, product-minded generalist who can help you go from zero to one—someone who can take vague ideas, messy whiteboards, and half-built code, and turn them into something users understand, trust, and love.

This person is probably mid-career. Too junior, and they’ll just do as they’re told. Too senior, and they’ll spend too long debating strategy instead of getting stuck in. What you’re looking for is someone in the middle: a lead-level designer who can think independently, is comfortable jumping between strategy and bug fixes, and is happy to roll up their sleeves for the next 18 months.

Crucially, they’re also someone ready to grow—someone who wants to step into leadership, and build out a team of their own down the line.

These designers are rare. Often they were the third or fourth design hire at a fast-growth startup. They’ve seen how the sausage gets made. Now they’re ready to step into the kind of role they used to report to.

Or they’re a mid-level agency designer who’s delivered a dozen zero-to-one projects over the last few years, knows how to work quickly and smartly, and is desperate to break out of the dying agency world—ready to own outcomes, not just interfaces.

This is a small window in their career—and a huge opportunity for you.

TL;DR

• Founding designers are hands-on generalists who can balance UX strategy and UI craft

• They thrive in chaos, move fast, and care about real user outcomes

• Startup or agency experience matters more than a big-name CV

• Look for someone who works with founders—not just for them

• Ideally, they’ll scale with the company and become your first design leader

Why This Role Matters So Much

Your founding designer won’t just design screens—they’ll shape how customers experience your product, how your brand feels, and how your company is perceived.

They’ll likely:

• Create your first onboarding flow

• Design your marketing site

• Help you pitch to investors

• Build your first design system

• Translate half-formed founder ideas into real products

You’re not hiring a service provider. You’re hiring a product co-creator.

But even more critically—they’ll help you solve some of your company’s most important growth and adoption challenges. Whether that’s getting users to sign up, activate, form habits, or convert, your designer will shape the moments where your product either clicks—or doesn’t.

They’re often the person who helps you iterate your way toward product–market fit—not by adding features, but by reducing friction, clarifying value, and improving the path to “aha.”

In the earliest days, design isn’t just about aesthetics. It’s about survival.

What to Look For in a Founding Designer

Here are the key traits that separate the right hire from the risky one:

1. Strong in Both UX and UI

A lot of junior designers over-index on visuals. Some senior designers are too abstract or slow. You need someone who:

• Can design intuitive flows and make them look great

• Understands user psychology and onboarding

• Can spot a friction point and fix it without a full redesign

They should care about clarity, usability, and aesthetics—equally.

2. Fast and Impact-Oriented

This isn’t a role for perfectionists. It’s for people who know how to ship quickly, iterate fast, and deliver value.

They care about quality—but they know shipped is better than perfect.

Ask them how they’ve made trade-offs. What they’ve shipped under tight deadlines. How they define “good enough.”

3. Process-Aware, Not Process-Obsessed

You don’t need someone to run a perfect double-diamond. You need someone who can design under constraints, with incomplete information, and get things out the door.

They’ll have a process—but they won’t let it slow them down.

4. Founder Chemistry

You’ll be working closely—daily. That means:

• They can extract clarity from your chaos

• They listen well and translate your intent into action

• They’re confident enough to push back when needed, without ego

The best founding designers feel like creative co-founders, not pixel pushers.

5. Thinks Beyond the Happy Path

As a founder, you probably have a strong mental picture of your product’s “happy path.” The ideal flow. The perfect onboarding. The user who never hits a snag.

But real users don’t behave perfectly. They forget passwords. Skip steps. Make mistakes.

A great designer will test your assumptions. They’ll map out what happens when things go wrong—error states, dead ends, edge cases—and fix those flows before they become engineering headaches.

It might feel frustrating in the moment—but working this stuff out in Figma is 10× cheaper than fixing it in code.

They won’t just build what you asked for. They’ll help you build what actually works.

6. Deep Empathy for Users

This person should be thinking constantly about:

• What it feels like to use your product for the first time

• How to deliver value quickly and reduce user stress

• How to guide users smoothly from signup to success

But more than that, great designers act as translators—between what you think users want, what engineers can build, and what users actually need.

Founders often gravitate toward the most obvious solution. Engineers often prefer the simplest or most technically elegant one.

Great designers choose the solution that best matches the user’s mental model—something that solves their pain in a way that feels effortless and intuitive.

That’s the difference between a product that works, and one people love to use.

7. Startup or Agency Experience

Designers from FAANG companies are often specialists. They’ve spent years designing one part of a mature system with lots of support. That’s not what you need.

You need someone who’s:

• Seen chaos before

• Worked fast and independently

• Taken ideas from nothing to live in the world

Agencies and early-stage startups tend to produce exactly that kind of designer.

8. Well-Connected

Not essential, but valuable. When you grow the team, you want someone who knows who to hire. Someone with a network. Someone people want to work with again.

9. Wants to Lead (Eventually)

You don’t need a manager today. But ideally, this person can grow into a design lead over the next 12–18 months.

They want more than just craft—they want influence. They want to shape culture, not just Figma files.

Common Mistakes to Avoid

Even experienced founders get this wrong. Watch out for:

• Hiring based on brand name, not experience
  A Google or Apple background might sound impressive, but it often means slow, process-heavy design.

• Hiring someone who needs too much direction
  You don’t have time to be their design mentor. They need to lead, not follow.

• Focusing only on aesthetics
  Your product needs to work, not just look good.

• Hiring your mate because it’s convenient
  They might not be the best fit—and it’ll be harder to course-correct later.

How to Interview a Founding Designer

Some useful questions to dig into:

• “Tell me about a time you shipped something quickly with minimal input.”

• “How do you approach onboarding a brand-new user?”

• “How do you decide what to prioritise in your design work?”

• “Have you worked directly with a founder before? What worked—and what didn’t?”

• “Can you show me something scrappy you’re still proud of?”

Look for signs of clarity, autonomy, humility, and adaptability. You don’t want a prima donna. You want a doer who knows what matters.

Write a JD That Speaks to Them

Most job specs are too vague or too formal. Write yours like a letter to your ideal hire.

Include:

• What makes this opportunity exciting

• What problems they’ll be solving in the first 3–6 months

• What kind of person this isn’t for

• What your vision is—and how design helps achieve it

You can also include a lightweight vision deck: screenshots, team structure, funding status, quotes from founders about why design matters.

See more on this here:
📄 Crafting Effective Job Ads
📄 Hiring Your First Designer – Seedcamp

Final Thought: Hire for What You Need Now (And a Bit Beyond)

You don’t need a Head of Design. You need someone who can:

• Design a homepage in the morning

• Tweak onboarding in the afternoon

• Clean up your pitch deck that evening

They’re not a service. They’re leverage.

Get this hire right, and they’ll shape your product, your brand, and your team culture. Get it wrong, and you’ll spend the next six months designing things yourself—or undoing someone else’s work.

Be deliberate. Be clear. And don’t just hire for the CV. Hire for the chemistry.

Need a second pair of eyes?
If you’re hiring your first designer and want help refining your JD or vetting candidates, feel free to reach out. I’ve helped dozens of early-stage startups get this hire right—and avoid expensive missteps.