Running an effective remote design team

Around this time last year, I got an interesting call on Slack.

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Automattic had recently organized its mobile teams into a new division called Hogwarts, and our new division lead Cate Huston had embraced her new identity. I was coming off of several weeks of time off after surgery to repair a nerve in my hand that I severed during a cooking accident. Feeling down and sorry for myself, I was having a hard time getting back into the rhythm of work. But I was jolted out of my inertia by the reason for Cate’s call: to talk about forming a mobile design team within Hogwarts, with me as its lead.

I love mobile design, and with a second product designer set to join Hogwarts, I knew it was the right time to start a design team. Despite having never really felt like much of a leader, I thought it made sense for me to do it. And so, the Ministry of Magic was formed. I was nervous at first, and made plenty of mistakes. But through a process of constant iteration not unlike how we make products at Automattic, I’ve gone from being a reluctant leader to an enthusiastic one. I’m far from an expert on this topic, but Hogwarts, once an organization where design was often an afterthought, has become one that has an effective design team at its center. Here’s a few of the things I’ve learned in my first year as a lead.

Continue reading “Running an effective remote design team”

I will never stop learning.

In the decade that I’ve been designing for Automattic, my job has taken many shapes. As the first designer working for the company, I was a generalist—I designed everything from the company logo to the WordPress.org website and the interfaces for our first products. While my time in college taught me a lot about art and design, almost everything I know about my career, I’ve learned here. Our company creed begins with those five words, I will never stop learning. It’s not aspirational—it’s a statement of fact. It’s impossible to work here for very long without being constantly inspired and challenged.

This year I’ve learned an incredible amount about something I’ve never thought I was good at: hiring. Earlier this year we formed the design hiring group at Automattic, a team of designers who, in addition to our regular duties, review portfolios, interview candidates, oversee trial projects, and recommend designers to our CEO. It’s a giant task, and deeply influential in how our company grows and our products evolve. If you apply for one of Automattic’s product or marketing design jobs, you’ll probably hear from one of us along the way.

When I started working on hiring, I was on my own, and I was pretty sure I was terrible at it. I didn’t cause any major meltdowns, but I had a complete awareness of how out of my element I was, and how much I had to learn. I knew I’d only get better with some help, so I asked a few of my colleagues to join and together, we have leveled up quickly, learning how to be comfortable in an environment that, as designers, none of us were all that familiar with. (I went through my fair number of job interviews after college, but my last one was in 2005!) Our efforts are already paying dividends, as we’ve gotten to see some tremendous designers join Automattic as a result of our recommendation.

Along the way, I’ve gotten to help with two major pieces of news we get to announce today. This summer, the design hiring group assisted with the monumental task of finding someone to become Automattic’s head of design. If hiring designers was intimidating, talking with some of the greatest minds in the industry about Automattic’s design was ten times so. But through that process, we learned an incredible amount about what we aspire to, and what we should do to get there. And as a result, we now have an amazing leader in John Maeda, our new Global Head of Computational Design and Inclusion.

One of John’s first ideas was to let the world know about the design culture we’ve been building, and today that idea has gone public in the form of Design.blog, a new publication from Automattic designers & friends. We’ll use it to profile the people who make design happen at Automattic (here’s mine), and to feature the voices of designers who inspire us to keep pushing ourselves to do more, and be better. Our first pieces are from Jessica Helfand, Cassidy Blackwell, and Alice Rawsthorn. Each are thought-provoking and inspiring, and I hope you’ll check them out.

In the decade I’ve been here, I’ve never been more excited about the state of design at Automattic. If you love design and are interested in what we’re doing, I hope you’ll join us.

Gone Fishin’

At the end of the day, I’ll begin a sabbatical from Automattic that will last until October. It will be the first time since 2004 that I’ve had more than two consecutive weeks away from work. The idea of not working for an extended period of time is all at once exciting, relieving, and terrifying. But I’m grateful to work for a company like Automattic that not only allows but encourages employees to take time off when they need it. As I take this break, it seemed like a good time to reflect on how I got here.

In the summer of 2005, Matt Mullenweg got in touch with me to do some freelance design work1. He was starting a new service called Akismet, and I built a very simple website to introduce it to the world. We worked well together, and a while later he asked me to design the logo and website for a new company he was starting called Automattic. It was the biggest project of my very short career, and was soon followed by a bigger one: the redesign of WordPress.org that launched in December 2005. In the middle of all that, Matt asked me to join Automattic full-time. And I said no.

It wasn’t that I was skeptical of Automattic’s prospects. But commitments are important to me. When Matt made the offer, I was just three months into my first real design job. The company had taken a chance on me, a self-taught web designer with a degree in print design, and had helped me move to Baltimore for the job. I told Matt that out of loyalty, I wanted to stay there for a year. But in my spare time, I continued to freelance for Automattic. And after that year was up, I decided to join full time. Yet after almost seven years, Matt still likes to introduce me to people by saying that I rejected him the first time he offered me a job. :)

My career at Automattic has been the most fun I could ever imagine having while working this hard. It’s been thrilling to help both Automattic and WordPress grow from their tiny beginnings. And I am nowhere close to done. The last survey taken by A List Apart shows that over half of the web professionals surveyed had been in their job two years or less. Just over 10% had been at the same company for seven years or longer. And no knock against designers who changes jobs more often, whether out of necessity or choice. But I’m inspired by designers like Dieter Rams and Jony Ive, professionals who built careers designing products largely for a single company. It’s certainly possible for a great designer to do good work for many different clients, without spending much time with any one of them. But I’ve never considered myself to be a great designer. I’m a designer who’s determined to produce good work, and I have to work hard at it. Creativity and inspiration do not flow through me like a typically “artistic” person. But I love design, I love the things I work on, and nothing excites me more than seeing that through for the long term.

So no, I’m not leaving Automattic. I’m planning to spend some time both relaxing and working to accomplish some personal goals I’ve been neglecting for too long. I plan on spending a little less time in front of my Mac. I hope to find a new place to call home. But most of all I’m looking forward to coming back to Automattic in the Fall with a renewed focus and energy for the work I love.


1 The TextDrive VC200 started my career. When I began teaching myself the basics of web development, I chose Textpattern to power my first blog. I signed up for the VC200, became involved in the TextDrive user community, and did some freelance work for them. Matt Mullenweg asked Jason Hoffman to recommend a designer, and the rest, as they say, is history.

New Orleans

Automattic’s Team Social came to visit New Orleans for a team meetup, and I had the pleasure of crashing it over the weekend.

Automattic in Seaside

Photo Credit: Donncha

Just settled in at home after a week in the ever-lovely town of Seaside, Florida with my Automattic homies. I learned a ton in the past week and had kind of a ridiculously good time in the process. There’s always the temptation to think how great it’d be if we could work together all the time. But then we remember these meetups are so cool because Automattic is made of people who make their homes all over the world. That said, I can’t wait to see them this spring in San Francisco. :)