A happy cupcake may not be the first thing you’d think of to explain Dropbox’s phenomenal success. But that image actually represents one of the file-sharing company’s five corporate values, and is a core part of a culture that CEO Drew Houston says has been vital to their business performance.


Houston was recently interviewed at Dreamforce ‘18 by Marc Benioff, Chairman and Co-CEO of Salesforce, last September. Houston shared insights into the culture underlying Dropbox, which began as a two-person startup in 2008 and has since grown to become a public company with more than $1 billion in annual revenue.


He began by describing how, as a 23-year-old MIT electrical engineering student, he first got the idea for a cloud-based file storage and file syncing system.


“It started in 2006 with a bus ride — the Chinatown bus from Boston to New York. I had all this work I wanted to get done, only to find out I’d forgotten my thumb drive,” he said.


“I was like, ‘I never want to have this problem again.’”


With four hours to kill, he decided to start writing some code — and Dropbox was born.


“I had one customer in mind — myself. But actually, those first lines of code were what blossomed into everything else, even though I had no idea at the time.”


Defining clear corporate values


Dropbox grew rapidly, and as its operations became more complicated, Houston began to think more deeply about how a positive corporate culture could help him lead the business.


“As a company gets bigger, the leaders get pulled in a lot of different directions,” he said. “One of the things that stresses you out as a founder is that you can only be in one room at a time — but for every decision you’re making, there are thousands of others being made without you in the room. So then you have to have mechanisms to help people make those trade-offs.”


Houston realized that while he couldn’t oversee every activity, he needed to know that his people would act in a consistent and responsible way. Clear core values — and encouraging people to follow those values every day — would enable that outcome.


“My co-founder and I realized that while we’ve always really cared about our company culture, we had never written it down. So, step one for us was to have that conversation: What's most important to us? Who do we want to be as a company? What kind of leaders do we want to be? We decided on five cultural principles that are really important to us.”


For Houston, the first value was an easy decision: Be Worthy of Trust.


“Trust is something you have to earn every day,” he said. “We feel a serious responsibility toward the people who are storing their most important personal and company information with us. We want to be the best possible caretakers of that in every way.”

Other values include Sweat the Details, Aim Higher, and We Not I. “Now, those first four are pretty good,” Houston said. “They’re a true set of principles that guide our actions, but they’re also very serious. That’s where the cupcake comes in.”


Drew Houston interviewed by Co-CEO of Salesforce Marc Benioff during Dreamforce ‘18


For Houston and his co-founder, Arash Ferdowsi, a culture that brought joy and delight to both employees and users was instrumental in attracting talent and driving Dropbox's growth, so they wanted a value that would represent their commitment to maintaining that. “I saw that one of our illustrators had made this drawing of this smiling cupcake. I thought, ‘Well, what if we just used that, not the word cupcake, not delight, not "don't take ourselves too seriously," but just that image of that smiling cupcake? So that's our fifth value”.


Creating a customer-focused culture


Houston believes that articulating a strong set of values helps to reinforce a customer-focused culture at Dropbox, where his people are invested in the efficacy of the product.

“I think you have to thread your values and culture throughout the entire operating system of your company, and then whenever you have problems or near misses, you have to have a culture of reflection about it and be like, ‘Okay, well, problems are going to happen, but how do we make sure we don’t have that specific problem again?’”


Keeping trust as a cornerstone


Houston pointed to the problems that can arise for high-growth companies when rapid success becomes more important than continuing to build a relationship of trust with customers.

“It can be easy to take trust for granted, especially when there are so many forces at play — when your investors are calling for more growth and your customers are calling for their products to be better,” he said. “But if you have a broken culture, then nobody really cares how well your business is performing, and nobody really cares how great your products are. Once you lose that trust, it’s really hard to get it back. It’s a bit like oxygen — you only notice once it’s missing.”


For Houston, even as his organization evolves and changes, core values like trust remain foundation stones. The company works hard to ensure that its values remain top of mind across the workforce through activities such as “Trustober,” a month-long focus on trust held every year in October.

“Trust requires eternal vigilance, and we’re never done,” he said. “At the end of the day, we’re a subscription service. We only survive if we do a great job for our customers.”


Watch the full interview with Drew Houston at Dreamforce 2018.