How “Structure” Saved MailChimp

The email marketing company’s staff was once a disorganized mess. But before fixing that, its cofounder had to fix himself.

- Jason Feifer

MailChimp’s tiny staff could once fit around a table, so they often did— gabbing over coffee, and dreaming up new directions for the business. By 2009, though, that team had grown to 300 people. At a company cookout, cofounder and CEO Ben Chestnut looked around and realized he barely knew anyone. So he called a meeting, hoping to reclaim the intimacy of those early days.

Hundreds of employees gathered. When it came time for questions, someone raised a hand and asked about MailChimp’s future plans. The CEO shrugged it off. “I’m giving this answer like, ‘We don’t need no stinking strategy—we’ll cross that bridge when we get there!’ ” Chestnut recalls. That, after all, had been his longtime philosophy: The company worked best when it improvised, trying things on the fly. But while half the room nodded in agreement, the other half seemed alarmed. One raised a hand and asked, “Why are you being so secretive?” The room got tense. Afterward, another employee told him he needed leadership training.