Designers: How to get a job at a startup

I’m a senior creative and I’ve hired designers for over 20 years, first at a couple small creative agencies I founded, then later at several small- to large-sized tech firms in Silicon Valley* such as Fitbit, Thanx, and CBS Interactive (when it was still CNET Networks).

Here’s some advice for job-seekers in the design field who are looking to get hired at a tech firm or startup company.

Illustration by Dean Drobot

Have kick-ass work in your portfolio

This should go without saying, but you wouldn’t believe how much time I’ve wasted in the last 15 years reviewing portfolios with terrible or lackluster work.

As a creative, 95% of what gets you to the first interview is your portfolio. It’s not your cover letter or résumé (I rarely see either), it’s only 5% your LinkedIn profile. I want to see the work you create and how you present and explain it.

Get a second opinion

So how do you know what kick-ass work is? Even the most self-aware designer can get too enamored with their own work. It’s hard to have perspective.

Get another designer or a trusted mentor to offer their honest opinions of your work. If they say something doesn’t fit in your portfolio, consider taking it out or strengthening its presentation. I’ve been a designer for 30 years and I still ask trusted colleagues to review my own portfolio before I put out an update.

Ambition’s great, but chill out

A colleague of mine recently said, “I can’t believe how many candidates I’ve interviewed lately who answered the question about their career with ‘I want to start my own company in 5 years.’ ”

Nobody’s going to hire you if they think you’re going to bounce in a year or two. “I might like to start my own company one day,” is sufficient.

Interview back

Don’t be totally passive in the interview, ask questions and probe how the company works. Make sure you really understand the role you’re applying for, the kinds of things you’ll be called on to do, and the types of people you’ll work with. A Senior Design role at a startup company can be very different from one at a large company or an agency.

How the team works and your role in it is one of the biggest factors to the fabled “right fit” that candidates and companies are both looking for.

Show that you’ve done the research about their product, market, competitors, etc.

I’m happy to tell you about the company I’m hiring for but I don’t want to spend 15 minutes every interview giving you the basics that you could’ve found out beforehand. If you’re not interested enough in a job to do 20 minutes of Googling and reading — or if you haven’t even checked out our website or downloaded our app — I’ve got 27 other candidates who have.

Stalk the people who work there

Okay, research them. Don’t really be stalk-y. But if you don’t know anything about the company or the people who work there, you don’t seem like a very interested candidate to me, the interviewer. That makes me less likely to select you, even if your work is equal to the other candidates I’m considering.

Bring cookies. Or mochi

We had a guy show up for his interview with a box of mochi to share with everyone. He made quite the impression and people were talking about him for weeks afterward. He wasn’t the most qualified fit, so he ultimately didn’t land the job. But the point is: In a crowded field, it can’t hurt to be easily remembered.

Don’t be greedy about your title

Have some humility. I can’t count the number of candidates I’ve interviewed who claim to be Senior Designers or Art Directors but who can’t actually demonstrate those capabilities when I dig into their work and ask about their specific role or individual contributions. If you’ve been a junior designer for 4 years you’re not leaping to senior designer just because you put in the years; you’ve got to demonstrate that you’ve gotten better, gained new skills, tried new disciplines, mentored other designers, something to have earned a better title.

You don’t get to be an Art Director because you’ve been a designer for 10 years. You get to be an AD because you demonstrated the qualities that an AD has to acquire with time and effort: leadership, higher-level design thinking, creative breadth, strategic awareness, ability to delegate, ability to collaborate, diplomacy, communication skills, and much more.

I actually saw someone ask a question on Quora that was something like “How do I get an art director job even though I have almost no experience to speak of?” *mind boggles*

Be flexible about your title

Most startups don’t have Senior Designers, Art Directors, and Creative Directors. Those titles exist at more mature companies, post-startup stage, where the design team has grown as the company has. If you’re joining a small team, don’t expect a fancy title. Everyone may be a Designer and it may take time for there to be clear design leadership, such that there are Senior Product Designers or whatever.

At the same time, if you get offered a job, feel free to negotiate (politely) your title. Startups have the luxury of not having layers of management and hierarchy, so it’s easier to make adjustments to things like titles. Even big companies can do this sometimes. Years ago I joined one of the world’s top 10 web properties, already with 10+ years of experience under my belt. Even though I was applying for a somewhat junior role, they offered to up my salary and title (I didn’t even ask — nice of them!), and they let me choose my own title. I chose Design Guy.

Do a quick redesign exercise (but do it on your own terms, and of your own initiative)

I normally strictly advise against doing work on spec (more on that in a moment), but there are times when it can really pay off. If it’s a job you really, really, really want — that one in a million that just seems like it’s made for you — pour your soul into it.

I hired a somewhat junior designer for a senior design position once, and a lot of that was because he took the initiative to redesign a bunch of screens in our mobile app. It was done without any of the inside knowledge we had, so there were things he didn’t foresee, but it showed he could do really good UI work and gave insight into his thought process. It also showed initiative and that he was hungry for the job.

When I was creative director of a small firm we once had lost a client pitch to another, cheaper company. I spent all weekend putting together a demonstration website of what we could do and sent it to the client founders. They changed their minds and engaged my company instead. It was spec work and a gamble, but it paid off — it was the biggest contract my design firm had ever landed.

Don’t do a design exercise on spec

It’s de rigueur for companies to ask candidates to complete a design exercise in order to gauge their competence and skill, but this is essentially work on specwork you don’t get paid for, on the speculation that you’ll get hired. There is industry-wide consensus that spec work is bad for the profession, but here’s what you can do instead.

Politely tell the company that spec work is against the code of all professional design organizations (AIGA, AdAge, RGD, UnderConsideration, HOW, SXSW, Crativepro) and you follow these principles (remember that they probably have no idea it’s a bad thing — from their perspective it’s great). However you’d be happy to consider one of these options:

  • A freelance business-specific design exercise — A limited, paid engagement for X hours at your hourly freelance rate. Company gets the “work product” at the end of engagement and upon receipt of payment.
  • A non-business-specific design exercise — A free consultation for X hours to whiteboard a design challenge that has nothing to do with company’s specific business, but that will still demonstrate designer’s process and ability to execute.

If you get offered a job

I’ve had friends make the following mistakes and regret them. I’ve made a few myself (don’t tell anyone). Here’s my advice:

Amend the work-for-hire and copyright sections of your employment contract

Almost all employment documents include “work-for-hire” language that basically says: you work for the company, so the company owns all the copyright and “work product,” and you get no rights to use it after you leave. In the case of a full-time gig this does make a certain amount of sense, because the company is compensating for your loss of copyright with pricey things like a work computer, software, health benefits, 401k plans, and whatnot. It also makes sense if you’re an engineer or scientist because the company wants to retain your inventions and can’t let you quit in a couple years then turn around and sue the company for using technology you invented.

Creatives, however, need to be able to show their work in a portfolio in order to get their next job, and the next after that. The default legalese in most employment contracts precludes this. But it can be easily amended to give you permission. Explain this scenario politely to your potential employer and they should understand (if they fight you, that’s a signal). Here’s the language I usually use:

Addendum 1:
Employee is authorized to place work done for Company in his/her public portfolio of collected work, provided such work is acknowledged as work done for Company and owned by Company. Notwithstanding and foregoing, Employee may not include in his portfolio any work that relates to any unreleased design or product development work undertaken for Company. Provided that, such design or product development work may in all events be included in Employee’s portfolio one year following presentation to Company, or such earlier time as authorized by Company.
[signatures, dates, et al]

Take equity if it’s a company that’s going to succeed

As a contractor or employee I’ve been offered equity as compensation for some of my work and sometimes I’ve taken it and sometimes I’ve declined. It’s not always easy to know when a company is a good bet. However, in hindsight it’s definitely easy to regret it when you didn’t take the opportunity and that company becomes a big success. Think if you had designed the logo for SpaceX or Nike and they had offered you half payment in equity — and you didn’t take it.

My advice is: Figure out the salary you need to live on, allow some percentage for retirement savings, cost-of-living increases, and emergencies, then figure out what part of the remainder makes sense to be compensated as equity.

Don’t forget to exercise your options when you leave

When you take equity and you later leave a company, don’t forget you have a limited time to “exercise” your stock options after your departure date. I’ve had friends make the mistake of not paying their fee in time. They could’ve been millionaires a few years later, but instead they were left with no shares because they missed the deadline.


*More accurately, “the greater San Francisco Bay Area,” since “Silicon Valley” really means the Santa Clara Valley in the South Bay, where silicon chipmaking first took hold in the 1970s and set fire to the much larger, Bay Area-wide tech industry we — decades later — refer to as Silicon Valley. However, the majority of the companies you think of as “Silicon Valley companies” are not in the actual valley known as Silicon Valley.**

**Call me a pedant, it doesn’t bother me.


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