10 lessons for building a design team from scratch

My name’s Davey and I lead the design team at Gusto. I was the first employee hired back in 2012, and I’ve been fortunate to watch the company grow from a dozen small business customers to over 25,000 today.

During this time, design at Gusto has grown a lot too. We’ve gone from one person struggling to do everything (hi!) to a real, bonafide design team. I hope this post will help other startups who are ready to make their first design hires. I know first-hand how difficult building a design team can be.

2015: A very big year for Gusto

2015 was a huge year for Gusto. We went from 60 employees to over 300. We expanded our customer base to all 50 states. We moved into a new office in San Francisco and opened an office in Denver. We processed over half a billion dollars in payroll in a month for the first time. We raised a new round of financing to grow the team. 2015 is the year it all came together. It all started to click.

It was also a huge year for design at Gusto. We rebranded the company from ZenPayroll to Gusto, which was a difficult (and emotional) experience that I hope to write about in the future. The team also grew from two designers to ten. That was a major transition for me personally. In the space of a few months, I went from diligently designing and coding each and every feature to interviewing, running team meetings, conducting design reviews and having a full day of back-to-back 1-on-1's.

Building a design team means more Slack, less RubyMine and Sketch.

Sometimes I look at my dock and see poor lonely iTerm, RubyMine, Sketch and Creative Suite, which I haven’t opened in days. What the heck happened? I miss you guys!

The reality is that the only real way to grow is to hire. I’m still figuring out how building a team works (I’m sure that’s a lifelong journey), but here are some things that I’ve figured out so far.

Lesson #1: You. Cannot. Scale.

You know that part of the Lord of the Rings where Gandalf yells at the Balrog: “You. Shall not. Pass.” And then he drives his staff into the bridge like a boss? The designer version of this is: “You. Cannot. Scale.”

I’m a huge Lord of the Rings fan.

As your company grows, you cannot do it all. You can’t. The work will win. It will smote your ruin upon the mountainside. So, you have to hire. And the sooner you start, the better.

Lesson #2: Hiring is part of your job.

When you reach the point where you need to hire another designer, hiring becomes an important part of your job — almost as important as designing. Ironically, when you’re really overwhelmed with work, it becomes even more important.

You might think: “No, my job is to make mock-ups in Sketch and then code them up.” Or, “I’m in charge of user experience; someone else can recruit, that’s why we have recruiters.”

That’s thinking functionally. You need to always think about the bigger picture, especially at a startup. If your responsibility is design, and you can’t do it all, then it’s your new responsibility to hire more designers.

Lesson #3: Hire for skills you don’t have.

You want to hire people who can do things you can’t. It’s easy to settle for a candidate with skills you’re familiar with and can easily evaluate. But my advice is to hold out for people who surprise you.

I think of Gusto’s design team as a Venn diagram with overlapping circles. Design is in the middle, but there’s magic in the periphery: illustration, photography, iconography, typography, JavaScript, WebGL and beyond. For you nerds out there: The design team’s capabilities are the union of the overlapping circles, not the intersection.

One of the most satisfying things I’ve experienced as head of design is watching a new team member grow the team’s skillset. For example, in mid-December Jenna Carando joined our team. Among many other things, Jenna is really good at hand lettering. Within a couple days of her start date, she created this custom image for Gusto’s first 2016 paystub:

I’m a designer, but this is something that I could not make.

It’s a small thing, but no one else on our team had the time or experience to make it.

Lesson #4: Interviews are 60 minutes. Never 30 minutes.

A lot of companies limit interviews to 30 minutes. I don’t think this is enough time. You need 30 minutes just to get to know someone and to share what makes your company special, and another 30 minutes to dig into their experience and skills.

Even 60 minutes is too little, to be honest. Beyond the formal interview, I often spend several hours emailing, chatting and having coffee with each candidate to whom we extend an offer. There’s a Silicon Valley mantra, “hire slow, fire fast” that has always irked me. If you have to fire fast, then you’re not hiring slowly enough.

Lesson #5: Work on the weekday. Plan on the weekend.

The day-to-day work of a designer requires a lot of hyper-focus. It’s not conducive to strategizing about the future of your team. Instead, I’ve found that I do my best recruiting and team thinking outside of work — late at night in my living room or over a Sunday cup of coffee at Philz. Some people do their best thinking in the shower. Or during a run. Figure out what works best for you and embrace it as part of your routine. Don’t stress yourself out because you’re fighting fires during the week and don’t have time to think about recruiting. That’s normal.

Lesson #6: Write down your design team values.

Once you’ve built a team of five or so people, sit down with everyone and reflect on the traits that make your team effective. What is it about design at your company that makes it unique? What skills do you value the most as a team? What kind of designers do you want to hire?

The Gusto Design Team Values

Codify these ideas into a set of values and refer to them frequently. I like to share these values with new candidates too. It gives them some perspective on what design at Gusto is all about.

Lesson #7: Hire like a Disney theme park.

Disneyland is a temple of great design. It’s engineered to create one of the most memorable days of your life. Check out this post on Help Scout’s blog and read the section entitled “When Does the Three O’Clock Parade Start?” The attitude that Disney looks for in its theme park employees is the attitude we look for in designers.

Lesson #8: Make a better pastry, not a better app.

This is my way of saying: create a design team that thinks about the end user. A lot of Gusto customers run bakeries. By making their payroll and benefits easier, we allow them to spend more time baking pastries. I like to think this means we ultimately bake pastries too.

A tasty apple pie from Three Babes Bakeshop (Gusto customer since 2013)

You may think that’s a stretch. But it’s how I think about design. How does our work improve the lives of our users? You want to orient your team to think this way, and as the team lead, it’s especially critical to keep it in the forefront of your mind at all times.

Lesson #9: Design for delight.

When you’re a solo designer at a startup, you’re preoccupied with making things functional and easy to use. The little time that’s left over is often dedicated to making things faster. Too often, what comes last is delight. And yet adding delight to a product is what makes it stand out.

How about that? An airplane with a bag full of money.

As you grow your team, you will have more opportunities to add delight. If you’re still too busy to do so, that’s a great indication that you don’t have enough designers. Everyone on the design team should have the space and time to go above-and-beyond what’s required and add magic to your product.

Lesson #10: Find a design mentor.

If you’re not sure how to build a team, or you’re not enjoying the process, seek advice. There are so many talented, experienced designers in the world, eager and ready to help, that you shouldn’t be bashful about probing your network. Last month, I was lucky enough to have John Zeratsky swing by one week and John Maeda the next. I always walk away from these meetings energized and tremendously excited. Their advice has real impact on how I build the team. Who do you look up to in your design community? Grab a coffee with them. It could be the best hour you spent all year.

Bonus Lesson: Create the role you love.

You may love solo design work, and dread the thought of managing a team. But don’t think of it as management. Think of it as giving you more time to focus on the things you really love doing.

The heart of design is about ideas — coming up with ideas, implementing those ideas and watching them succeed, fail or evolve in the hands of real people. You don’t have to spend 10 hours a day on your computer to be a designer. In fact, spending time with people who love design and talking, brainstorming and building together is even more rewarding. Your team should feel like a family; your role should feel less like work and more like play.

By the way, we’re hiring…

Thanks for reading, I hope these ideas were valuable to you. As you might expect, we are hiring too. Gusto is a startup dedicated to improving the employer-employee relationship, starting with compensation and benefits. But that’s really just the beginning.

We’re looking for product designers, UI engineers, interaction designers, visual designers and copywriters. You will like it here, I promise.