If you’ve walked around San Francisco or New York City this past year, you might have seen our mascot, Frederick von Chimpenheimer IV, looming overhead. Or maybe you’ve noticed him winking tirelessly into your office, day and night.

Freddie’s playful intrusion of privacy and public space has been great fun to work on this past year. It started as a casual half-idea:

FRIDAY, DECEMBER 30, 2011. MAILCHIMP OFFICE—EVENING
(Hurrying home for the holiday, BEN CHESTNUT pokes his head back in the door toward JULIE and LAIN.)

BEN CHESTNUT: "Hey, wouldn’t it be fun to have a MailChimp billboard?"

(Cue smoke machine.BEN CHESTNUT recedes slowly into darkness. JULIE and LAIN turn to one another, confused. Fade out.)

Ben’s idea gave me a wonderful opportunity to learn about billboards (ahem, excuse me: "out-of-home media"), something I’d totally dismissed before.

Defining Purpose and Success

At first I was pretty conflicted about the whole endeavor. I really enjoy helping MailChimp sponsor events by organizations like Living Walls and Flux Projects—they engage people in unexpected places with public art that’s beautiful and interesting and weird. Adding another advertisement to the quiet assault of corporate clutter seemed like the exact opposite of that.

After a brief discussion about exactly why MailChimp would want a billboard, the consensus was that we wouldn’t try to sell anything, we wouldn’t pander to anyone, we wouldn’t even advertise any features, like our new drag-and-drop editor (though that is pretty sweet). Instead, we just wanted to make MailChimp users smile.

When return on investment is measured by delight instead of sales or conversions, there’s a lot more freedom to be creative, to be bold, or maybe even to be creative and bold. It was liberating to begin the project knowing that our metrics were much closer to Bhutan’s Gross National Happiness Index than the kind of metrics that analysts or shareholders of a public company might expect.

Navigating Out-of-Home Media from Home

The first item of business was identifying the cities where MailChimp has a lot of users: London, New York, Sydney, Melbourne, Toronto, Brisbane, Paris, Singapore, and San Francisco.

Then, Julie and I picked a handful of cities and went crazy on Google Maps Streetview, picking out highly visible displays in strategic locations. This part was probably the most fun—like playing Myst, but with a lot less load time, no CD-ROM, and fewer goosebumps (thank goodness).

Once we’d found our favorite displays, however, it wasn’t as easy as emailing the media company to tell them "we’d like to start right away, please." And it’s not like these displays come cheap either. Eventually we decided that one city would be just fine for an initial experiment. We chose San Francisco because there’s plenty of inventory, and our users tend to flock there.

Julie and I sent several dozen emails back and forth with sales reps. Some of them tried to ply us with tickets to football games, some immediately smelled the naïveté on me, and others didn’t need our business enough to email back. Only after we sent these dozens of emails did we have to wait an inordinate amount of time (like, months) for the exact right board to be open at the exact right time. And once the board was available I had a few minutes to sign a contract before someone else snapped it up.

Finally, it was time to decide what to put on our first-ever billboard. This was a little stressful. I have so many puns to share with the world, but where to start?!

After everyone listened to all my puns, we instead decided to use a single winking, floating Freddie head. MailChimp users who spend hours of their time working inside with app would recognize Freddie immediately. He’d respond with a knowing wink.

Measuring Confusion and Delight

Our first experiment was in San Francisco’s SoMa neighborhood for a few months last Spring, and I had the pleasure of measuring our results. Every couple of days someone new would post a new picture of Freddie. Most were happy to see him, some were confused, and a few were worried that nobody else would "get it." Dozens of pictures *of a billboard* popped up during the entire three month span, and only one person seemed annoyed.

Since our initial test in San Francisco, we’ve started two new experiments in Manhattan and Palo Alto.

The art on the billboards is slightly different, but reactions have been similar. Thankfully, folks are taking fewer pictures of Freddie while driving on 101 South in Palo Alto.

I wouldn’t be surprised if other displays crop up soon. Keep an eye out for Freddie, and if you happen to stumble across him, let me know if you smiled—I’m serious about our return on investment.