How to Dunk on a Design Leadership Job When You Apply

I’ve been running my design studio full-time for more than two years now, but about once a year I get an itch to see what’s out there.

Is there some opportunity worth trading away the freedom and independence I enjoy now? Some grand scheme, perfect role, or giant payday? Or, like, non-terrible health insurance? Sometimes it’s good to look, even if you’re enjoying what you do.

The Itch & The Pitch

Last year the itch hit me in March. After a great first year in business, the studio had a slow start on year two. We bid a couple of large scale multi-disciplinary projects, but didn’t get either. Left with some free time, I dove into side projects, and started lazily poking around the job boards. And then, surprisingly, one caught my eye. 

An organization I was familiar with had a new role that sounded alarmingly like me. I read the job post to my wife, who said, “That sounds alarmingly like you…” and she suggested I apply. All I had to do was figure out how to do that. 

Sean Bean Mordor

One Does Not Simply Email in Their Resume

Here’s the thing — if you’re applying for a high level design job, it’s logical to make it a high level design experience. Even if the role is more design leadership than design contribution, first impressions matter. 

So of course I did the easy thing and built a website1.

A couple of days later, on a Saturday, I emailed the CEO a short message with the URL, and I got a glowing reply back before the end of the day. By Monday I had a string of team interviews scheduled for the week. 

And they all lived happily ever after, right?

Hard Work & Talent is Still No Guarantee

If the goal was to make an impression and get an interview, it was a successful endeavor. If the goal was to get a job, it was not so much a success. After some internal reorganization, they didn’t hire the role I applied for. These things happen.

But (!) I did learn a few things in the process:

Every job and every organization is different, but more importantly, you’re not everyone else. So don’t act like it. 

When you apply for a job, be you, be creative, and put more work into it than anyone should reasonably expect — not because prospective employers necessarily deserve it, but because it speaks to the kind of person you are, and the type of work you do.

You might not get the gig, but you never know what could happen next!


1. For the curious, you can visit, the site I built for Dribbble’s Director of Design & Brand role that didn’t happen. It’ll be live until the domain renewal comes up.