Hiring your first designer

In early 2020 I decided to join a startup as the first designer. I was looking to be an IC for a year or so, eventually transitioning into a Head of Design role and building out the Design team.

This doc is for small teams looking for their first designer, but unsure where to start or what to look for.

What do you need?

The first design hire often sets the tone for the rest of the Design team. Below are some questions to help guide what kind of designer you’re looking for:

Do you need them full time? Do you actually need someone right now? Is there some low hanging fruit that a contractor or advisor can help with?
What skills do you need from a designer right now? What about a year from now? Product designers operate on a wide spectrum from: research, scoping, user journeys, wire-framing, visual design, and writing code. Do you need a generalist who can do it all? A specialist to help you establish your aesthetic and design system?
Do you have both Product and Brand design needs? Asking a Product Designer to do brand design work (and vice versa) can sometimes be challenging as there’s not typically a clean transfer of skillsets. It’ll be helpful to draw this distinction and set expectations for candidates.
When are you trying to land them? Some designers want to be very early, some want some more stability. I was looking to be as early as possible, ideally smaller than 10. In my experience, the longer you wait, the more design and UX debt will build up and the less likely that Design will be a central part of the culture and DNA.
Do you want a leader or just someone to execute on your vision? If you’re looking for a thought partner, they should have some familiarity with the industry, or be able to grok it and ramp up quickly.
Do you want a partner that you’re in the weeds with? Or someone you can trust to just run with it so you can focus on other things?
Do you want them to evolve into a Head of Design, responsible for hiring and building out the function? If so, hard skills may not be as important.

How should you interview?

There are three main facets for the on-site:

Portfolio review (presenting their previous work). Do they understand the problem and the user? Was that solution appropriate? What was difficult? What would they do differently? How is their visual and interaction design skills?
Interaction/UX. White-boarding exercise with the goal of building out a flow with wireframes. Looking for: macro and micro interaction design abilities. This gives the best sense of what it’s like to work shoulder-to-shoulder with them.
Ideation. White-boarding exercise with the goal of being generative/blue-sky, tossing as many ideas on the whiteboard for a solution, ending in a synthesis and elevator pitch of one. Looking for: ability to be generative and unrestrained, how creative they are, and ability to synthesize and focus when it matters.

That said, when hiring the first designer, I’d put a bit more focus on soft-skills rather than the hard-skills (visual, UX, etc), assuming you want someone who will lead Design, and not just execute on someones vision:

Autonomy + ownership. You should be able to point them at a problem and let them go. They’ll let you know what they need (access to users, etc) when they need it.
Being a method actor. Removing their own bias + not designing for themselves. This designer is probably not going to be a daily user of your product, so you’ll want to look for someone who can empathize and understand your users (tools they use, UX/UI patterns they expect, etc) and design for them.
Learnability. Do they exhibit skills that showcase their ability to ramp up quickly?

Lastly, I’d also rate technical ability/acumen fairly high for your first hire (especially if they can push a few design PRs) assuming your product is fairly technical in understanding and users. It’ll help them not create Design in a silo moving forward.

If you’re not fully confident in the hire, or just want more hands on time, a contract-to-hire setup can be quite illuminating. I did this with Hex — I was not yet ready to commit, but getting a few weeks of work in solidified the decision for me (and probably for them).

What should you pay?

As always with comp, there are many variables at play. I was coming in with senior experience, but had yet to prove myself as a Founding Designer / Head of Design. As with most early hires, the upside of equity tends to be the most attractive piece, with cash acting mainly as a “maintain your quality of life” lever.

Below are my final offer details from four companies (all based in San Francisco, April 2020):

Company A: 4 employees | $180k, 1.75% | $3.7MM seed
Company B: 4 employees | $179k, 2.586% | $3.6MM seed
Company C: 4 employees | $180k, 2% (first offer was $140k / 1.5%) | $3MM seed
Company D: 10 employees | $140K, 0.75% | $3.5MM seed