Build Design Systems With Penpot Components
Penpot's new component system for building scalable design systems, emphasizing designer-developer collaboration.

medium bookmark / Raindrop.io |
Here’s something I couldn’t have imagined writing just a few weeks ago: after three and a half years, I’m resigning as Senior Director of Design at MailChimp.
Those few words, recently shared with senior leaders, colleagues and team members, marked the end of one of the most remarkable experiences of my adult life. An experience — from day one — full of exhilarating highs, challenging lows, and everything in between. An experience which taught me a great deal about leadership, business, building teams, and managing people. An experience which allowed me to be inspired some of the most warm, brilliant, creative people you could ever meet. An experience so unique, it could never be repeated.
As Senior Director of Design, I was the lead creative for nearly everything which touched the MailChimp brand — from product to marketing to award-winning advertising campaigns. I helped establish design’s “seat at the table” at the senior leadership level, working alongside VPs and Cs on a variety of projects. With the support of our CEO Ben Chestnut and fellow directors, I also founded an entirely new Design department which grouped all brand, marketing and product design functions together. Over the past couple of years, design grew from just a handful of designers embedded in separate departments to a distinct Design team of nearly 40 with an entirely new career ladder, managers, directors, operations, and overarching mission.
My MailChimp Design family in an impromptu photo just before my last day.
The role was a lot to take on, and lord knows I got over my skis more than once, but the pace at which we were growing and moving was exhilarating. At times, perhaps even intoxicating. Every day presented a new set of challenges, some of which I had plenty of experience with, while others were completely new and foreign. I had never led a design team this large before, so I was constantly learning, listening, and pushing myself to be a better design leader up and down the org chart.
I knew that another wave of growth and change was imminent for 2018, including the hiring of more leaders and a realignment of my own role to be less stretched (which I was looking forward to), but soon after the new year started I could sense something was off. I was still super involved and very much enjoyed working with everyone, but something within me had definitely changed.
Eventually the truth came out in a gloriously messy, tearful outpouring of emotion with my closest colleagues. I was done, and as painful as it was to admit, the time had come for me to go.
I had given MailChimp everything I had for three and a half years, and as much as I wanted to stay and continue building the team, growing MailChimp’s brand, and improving our products, the years ahead wouldn’t be the same as the years I once knew, and it was clear there was no longer a viable role for me in MailChimp’s future. I also knew, in my heart, that after years of focusing all my energy and attention towards work, I needed to try my hand at something new.
As sensational as it would be to announce I’m joining another company and moving further-up the career ladder of life, I’ve decided to take the opposite approach.
You see, I’m a dad, with kids ages 9 and 12, and my window of opportunity to be the kind of awesome, supportive parent I’ve always strived for is rapidly closing. I don’t want my kids to remember growing up with a dad who was distant and constantly thinking and talking about work. Or worse, a dad who voluntarily worked during his time off to catch-up and get ahead (a nasty habit I’ve been practicing since before they were born). As a working parent with similarly busy children, I’ve always tried to make up for lost time and attention on weekends and vacations, but it’s never felt like enough.
Being together in person is easy. What’s hard is actually being present.
So instead of immediately pursuing a new design leadership role elsewhere, I’m going to take this opportunity to unplug, reset and realign. I’m going to travel, write, shoot, read, and simply be around when my kids get home from school. I’m going to live life for a while without a title or a business card. I’m going to see what life looks like being no-one else but…me.
I have no idea what to expect, for I’ve never done anything like this before, but others I’ve spoken to who’ve taken similar breaks in life have told me I’m absolutely doing the right thing. I’m excited, yet honestly a bit terrified to be jumping off a comfortable branch into the unknown, but so far at least, it already feels liberating, powerful and rejuvenating. Let’s hope that lasts.
To my friends and colleagues at MailChimp, thank you. 🙂 You made me a better person than the man who walked through the door three and a half years ago, and I’m so incredibly grateful for everything I learned during our time together. For as they say, it’s not the destination that matters, but the journey getting there. Be well, and keep in touch.
AI-driven updates, curated by humans and hand-edited for the Prototypr community