Design's hardest role has a two-year clock

Happy Thursday.

Kevin Twohy spent the first half of his career as the first designer at early startups, before the title was in vogue. Around the 18 month mark he lost interest and got bad at it. Not burnout. The zero to one arc had ended and the job he was hired to do no longer existed.

Founding designer is one of the most sought-after roles in our Dive talent network. We hear from 13 people on today's show, from first designers to founders who hire them.

They describe the same job, but they don’t always agree on who should take it.

– Tommy Geoco

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Two jobs wearing one title

Kevin splits the role into capital F and lowercase f.

Capital F means the founder expects a peer, steering the business and not just the product and the brand. If the word founding carries its weight, he says, you should be paid for it in cash and equity relative to the risk. Lowercase f is a first designer, sometimes a junior one, with a word out front that makes the role more attractive.

Tom Johnson at Vercel draws it from the other side.

Founding the direction of a product is one job. Being the first designer on a product that already has market fit and a culture is another. Ask whether your founder has worked with designers, and whether they can drop what they built when the market says to.

Kevin's question separates them.

“In my first eight months, what decisions are going to be put under my purview?”

If nobody can name a decision that was yours by month eight, the word founding was marketing copy.

Getting that interview is its own problem. Dan Mall politely critiqued a cold DM from a designer volunteering his help.

I had a response: lead with something relevant to the person, and know it might not get you the job.

Everything is your problem

Jared Erondu has taken this seat several times, now at Span.

Everything is your problem, he says, but everything can't be your priority. His check on whether you are still close to the work: if it’s been more than five days since you talked to a customer, fix that this week.

He reduces founder trust to alignment plus execution: learn the bar in the founder's head, then argue any gap in business terms.

He dropped a bar that I’m stealing: the right thing at the wrong time is the wrong thing.

Jacob Jolibois has been the founding designer at his last two companies. No process. The job description is not accurate either, because you will also do brand, web, decks and things that are not design. Everything in his Linear is marked urgent right now, which is what he means by no priority other than urgent.

When it ends

Kevin's fifth rubric: longevity.

The role stays the same for 18 months to two years, then it becomes something else and you are the most tenured designer on the team.

Ask where you want to be in year three before signing for year one. If you are 18 months in and quietly worse at this than you were, check whether the job you were hired for still exists.

Jess Rosenberg left AirOps after about a year. Nothing was broken. No bad boss, no blowup. She had built the brand and team she came to build, and two weeks off showed her the sprint wasn't sustainable.

The question she asked herself: have I given myself permission to be finished?

It's a hard role, arguably one of the hardest, it burns a lot of people out, often if you're willing to become a founding designer and if you do well, you have the pain threshold to be a founder, and you might even have the chops.

But also: know when to say "I've done my job, time to move on."

Founding designer and designer founder are still separate jobs. One steers a company somebody else owns.

Founding Designer, live today on Dive Radio

Ridd and I go live today, Thursday, September 17, at 1 PM Pacific reacting to these submissions and more. In case you missed it, last week's hiring episode is still up and it’s a banger.

See you in chat.

— Tommy