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The Epic Fail of Mailchimp’s Rebrand

David S.
7 min readOct 12, 2018

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Mailchimp is email marketing service and was a brilliant brand. The service has tons of features, organized email lists, and best of all is free up to two-thousand users. It was always rough to create emails: no drag n drop design, endless warnings about images crushing inboxes, awkard template saving that made it hard to use previous designs. Add this to the struggles of African internet, when it was time to send an email update, I would plan on a long afternoon. I resize images for a living, I can’t imagine what the process was like for someone without photoshop!

Mailchimp describes the process in a blog post:

You’ve spent hours crafting the perfect email and segmenting the audience just right, and you’re finally ready to send. Freddie’s hand hovers over the big red button, nervously shaking. You click send, hold your breath, and….

But Mailchimp had that cute monkey Freddy. . .and when he gave you a high-five you felt like you conquered the world. The pain of the struggle turned to endorphins, and strangely enough, you walked away from the computer with the same feeling as completing a 10k: ELATION!

I don’t think this can be overestimated. Mailchimp’s greatest strength was not creating a frictionless email system. It was creating the maximum possible amount of friction that a user could bear, then celebrating the user for overcoming the obstacle.

Freddy and the high-five were at the heart of this.

Yesterday I received an email titled “What’s New in Mailchimp?” I was intrigued that Mailchimp is offering postcards.

Cool! I live in Africa, and it would be helpful to send postcards from time to time.

Oh, and in addition to postcards, Mailchimp has undergone a rebrand, read the story. I am curious why cute Freddy has been replaced by animated Dr. Seuss birds. Hmm, I’ll click on that. Oh my dear word. . .

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David S.
David S.

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