In MIT visit, Dropbox CEO Drew Houston ’05 explores the accelerated shift to distributed work

When the cloud storage firm Dropbox decided to shut down its offices with the outbreak of the Covid-19 pandemic, co-founder and CEO Drew Houston ’05 had to send the company’s nearly 3,000 employees home and tell them they were not coming back to work anytime soon. “It felt like I was announcing a snow day or something.”

In the early days of the pandemic, Houston says that Dropbox reacted as many others did to ensure that employees were safe and customers were taken care of. “It’s surreal, there’s no playbook for running a global company in a pandemic over Zoom. For a lot of it we were just taking it as we go.”

Houston talked about his experience leading Dropbox through a public health crisis and how Covid-19 has accelerated a shift to distributed work in a fireside chat on Oct. 14 with Dan Huttenlocher, dean of the MIT Stephen A. Schwarzman College of Computing.

During the discussion, Houston also spoke about his $10 million gift to MIT, which will endow the first shared professorship between the MIT Schwarzman College of Computing and the MIT Sloan School of Management, as well as provide a catalyst startup fund for the college.

“The goal is to find ways to unlock more of our brainpower through a multidisciplinary approach between computing and management,” says Houston. "It's often at the intersection of these disciplines where you can bring people together from different perspectives, where you can have really big unlocks. I think academia has a huge role to play [here], and I think MIT is super well-positioned to lead. So, I want to do anything I can to help with that."

Virtual first

While the abrupt swing to remote work was unexpected, Houston says it was pretty clear that the entire way of working as we knew it was going to change indefinitely for knowledge workers. “There’s a silver lining in every crisis,” says Houston, noting that people have been using Dropbox for years to work more flexibly so it made sense for the company to lean in and become early adopters of a distributed work paradigm in which employees work in different physical locations.

Dropbox proceeded to redesign the work experience throughout the company, unveiling a “virtual first” working model in October 2020 in which remote work is the primary experience for all employees. Individual work spaces went by the wayside and offices located in areas with a high concentration of employees were converted into convening and collaborative spaces called Dropbox Studios for in-person work with teammates.

“There’s a lot we could say about Covid, but for me, the most significant thing is that we’ll look back at 2020 as the year we shifted permanently from working out of offices to primarily working out of screens. It’s a transition that’s been underway for a while, but Covid completely finished the swing,” says Houston.

Designing for the future workplace

Houston says the pandemic also prompted Dropbox to reevaluate its product line and begin thinking of ways to make improvements. “We’ve had this whole new way of working sort of forced on us. No one designed it; it just happened. Even tools like Zoom, Slack, and Dropbox were designed in and for the old world.”

Undergoing that process helped Dropbox gain clarity on where they could add value and led to the realization that they needed to get back to their roots. “In a lot of ways, what people need today in principle is the same thing they needed in the beginning — one place for all their stuff,” says Houston.

Dropbox reoriented its product roadmap to refocus efforts from syncing files to organizing cloud content. The company is focused on building toward this new direction with the release of new automation features that users can easily implement to better organize their uploaded content and find it quickly. Dropbox also recently announced the acquisition of Command E, a universal search and productivity company, to help accelerate its efforts in this space.

Houston views Dropbox as still evolving and sees many opportunities ahead in this new era of distributed work. “We need to design better tools and smarter systems. It’s not just the individual parts, but how they’re woven together.” He’s surprised by how little intelligence is actually integrated into current systems and believes that rapid advances in AI and machine learning will soon lead to a new generation of smart tools that will ultimately reshape the nature of work — “in the same way that we had a new generation of cloud tools revolutionize how we work and had all these advantages that we couldn’t imagine not having now.”

Founding roots

Houston famously turned his frustration with carrying USB drives and emailing files to himself into a demo for what became Dropbox.

After graduating from MIT in 2005 with a bachelor’s degree in electrical engineering and computer science, he teamed up with fellow classmate Arash Ferdowsi to found Dropbox in 2007 and led the company’s growth from a simple idea to a service used by 700 million people around the world today.

Houston credits MIT for preparing him well for his entrepreneurial journey, recalling that what surprised him most about his student experience was how much he learned outside the classroom. At the event, he stressed the importance of developing both sides of the brain to a select group of computer science and management students who were in attendance, and a broader live stream audience. “One thing you learn about starting a company is that the hardest problems are usually not technical problems; they’re people problems.” He says that he didn’t realize it at the time, but some of his first lessons in management were gained by taking on responsibilities in his fraternity and in various student organizations that evoked a sense of being “on the hook.”

As CEO, Houston has had a chance to look behind the curtain at how things happen and has come to appreciate that problems don’t solve themselves. While individual people can make a huge difference, he explains that many of the challenges the world faces right now are inherently multidisciplinary ones, which sparked his interest in the MIT Schwarzman College of Computing.

He says that the mindset embodied by the college to connect computing with other disciplines resonated and inspired him to initiate his biggest philanthropic effort to date sooner rather than later because “we don’t have that much time to address these problems.”