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Dropbox exec outlines vendor's journey into a remote-work world

Dropbox exec outlines vendor's journey into a remote-work world

Almost two years after Dropbox announced it would become a virtual-first company, Andy Wilson, director of product, talks about why hybrid-work was never an option and what lessons the company has learned.

Andy Wilson (Dropbox)

Andy Wilson (Dropbox)

Credit: Dropbox

As the COVID-19 pandemic continued to surge in October 2020, most office workers found themselves entering the seventh month of home working. 

With vaccines on the horizon and (pre-emptive) rumours that offices would start to reopen in the new year, some organisations decided never return to an office-based environment — at least not one recognisable to the pre-pandemic way of working.

Dropbox was one of the first to make that decision, announcing on October 13 that “starting today, Dropbox is becoming a Virtual First company.” In a statement, the company said, “remote work (outside an office) will be the primary experience for all employees and the day-to-day default for individual work.”

Existing offices shut for good and in their place, Dropbox Studios opened for collaboration and community-building. Using the studios for solo work was strictly forbidden.

Almost two years later, Andy Wison, director of product at Dropbox, spoke about the experience of becoming a “virtual first” company and what lessons Dropbox has learned along the way. This interview has been edited for length and clarity.

Why did Dropbox decide to become a fully remote company and how did you go about developing your ‘virtual first’ strategy?

"We are a company that builds products that enable people to work remotely, so very early on in the pandemic, we decided we needed to live our product truth, by working remotely and learning what works with our own teams before releasing our products into the world.

"‘Virtual first’ [the name Dropbox gave its remote work strategy] was a very thoughtful process. We didn't just sit down and say: 'We're all remote now, let's keep it that way.' We spoke to lots of other businesses that had been working remotely pre-pandemic, asking what had been successful for them, what was challenging, what processes they had put in place, and from those conversations we started to build our new company strategy.

"For Dropbox, virtual first means that our primary place of work is remote, but it doesn't mean that we won't ever come together. We replaced our offices with studios so colleagues can come together to collaborate with their teams; however, it was important that people didn’t swap coming into the office with coming into a studio five days a week. 

"We don’t want our employees to say: 'I'm going to be in studio, Monday and Tuesday every week,' because that creates a proximity bias, and we didn't want to go down that route. We wanted to truly live that approach of working remotely and to understand what that would mean to have people working wherever they wanted to in the world."

When developing your new strategy, why did you decide on the remote working route rather than adopting a hybrid model?

"Through the development process, lots of different models were weighed up. At the time we were making these decisions, people were thinking that maybe we'll get back into the office early 2021, so we actually evaluated lots of different working models before settling on virtual first.

"We ended up ruling out taking a hybrid approach because we didn't think it would ultimately be equitable to all our employees in the aftermath of the pandemic. We’d already started expanding our hiring pool geographically and didn’t want to be limited by location moving forward."

And as the world started to emerge from the pandemic, how did the strategy evolve?

"Underneath virtual first is a number of tenets that define how we think about the future of work. One of those is ‘asynchronous by default,' the idea being that if we're going to have people working remotely, that shouldn't mean they spend eight hours a day on video calls. Instead, at Dropbox, you're measured on your output and the impact that you make, rather than how many meetings you can sit in.

"That then led us to think about how much time we should be spending in meetings, and as a result, we rolled out something called ‘core collaboration hours’ where employees reserve four hours each day to be available for meetings. That means there’s times when you're open to meet with your team or anyone else in the company, but also that you've got those other four hours in the day to focus on the work that you need to do.

"Does that mean you wouldn't flex that to meet with somebody who's in a different time zone or something else? Absolutely not. It's your time to manage as an individual, because we're measuring you on the impact and output that you're making.

"Something like a-synch by default also means that you're thinking differently about how you use your time. It’s a precious resource and we want our employees to learn to value it more. It’s also really important that as a company we try to keep work human. 

"We want to get this strategy right, but it's an iterative thing. We know that on the way we're going to have to nudge it a little bit to get things on course and we’re still learning as we go. But I think that what’s important is that if at the heart of it, we tried to keep everything human and build a collaborative work environment that's very flexible, then ultimately, that's all right."

How was the decision to go fully remote received at the company?

"Before we made the announcement, we ran some surveys at the company and we found that around 74 per cent of our workforce wanted to work remotely, for either some or most of their time.

"Then, after about six months of working remotely, we surveyed our staff again, and what we found was that people liked the flexibility. We repeated the survey again at the end of 2021 and found that by Q4 of 2021, around 63 per cent of respondents had adopted the async by default approach and over 80 per cent had adopted core collaboration hours.

"What was really interesting is that 72 per cent said that they felt more productive as a result of the changes, which is amazing, and that same number, 72 per cent, felt that they had a better work life balance, which is one of those things that helps to make work more human. We want our employees to have a real life, we want people to have the flexibility and to take ownership of their deliverables and how they balance their work.

"Throughout this whole journey, we have absolutely listened to the company and been sure to continually ask them if this is how they want to work."

What have been some of the challenges you’ve faced since adopting your virtual first working model? 

"When we first rolled out virtual first in October 2020, we were all still in this rather bizarre pandemic-induced environment, so at that point, it wasn’t that much of a huge shift because most people were still in lockdown and working from home. As a result, the immediate implementation of the strategy was probably much simpler than it otherwise might have been.

"I wouldn’t say there’s been any particular challenges, but we have had to change how we think about a lot of things we used to take for granted. For example, when hiring, you have to start thinking differently because all of a sudden, you're hiring from anywhere.

"I've hired five people in the last six months, all from very different locations around the world. At the start, it did take a little bit of a mind shift, but it also means we’ve now got a much bigger talent pool to recruit from.

"We put training in place to help managers hire remote talent, form remote teams and ultimately get all these new virtual employees to work together and build bonds, as that’s a very different experience when you’re used to doing all those things in-person. We also ran workshops with employees about how to brainstorm virtually, how to manage their time, how to manage project deliverables, to how to implement core collaboration hours in a way that would work for them.

"Opening up the studios has also provided a real opportunity for Dropbox; it’s the next chapter in how we work together. Where and when we can, we’re aiming to bring teams together at least once a quarter in either our permanent or on-demand studio spaces.

"However, getting together in person is purely so we can focus on generating ideas and connecting with each other, it’s not about using the space for holding in-person meetings. That's really important to us and, as a result, our studios don't have desks because that's not the purpose of them. They're for getting people together, creating ideas, moving things forward."

What have been the biggest benefits of of “virtual-first”?

"It allows us to come back to our mission as a company, which is building a more enlightened way of working. It also allows us to live our product truths, as not only are we building tools for remote workers, but we can prove they work because they’re underpinning our own work strategy.

"In terms of benefits to our employees, people working at Dropbox routinely say they feel more productive and have a better work life balance because they can take control of their working hours and flex time in a way that works for them, which is so important to us.

"The other really important thing we've done is get better about protecting people's time away from work by introducing something called ‘unplugged paid time off.' Because we’re all so used to getting communications via lots of different tool, including your mobile, when you take time off, it can sometimes be difficult to separate yourself from work when your emails are in the palm of your hand.

"So, we introduced something called unplugged PTO, which means that when you sign up to take your holiday, you just tick a box saying: 'I'd like to get unplugged,' and then when your holiday starts, we turn off notifications and disconnect all of your accounts until you return.

"We're really trying to think about that well-being aspect, because one of the biggest challenges with having a remote workforce is making sure your employees properly disconnect. We're trying to think through ideas like that to make sure all our workers have a better employee experience and as a result, we’ve seen 1.7 times increase in the number of people applying for jobs at Dropbox."

What have the biggest lessons Dropbox has learned throughout this experience?

"The first is that great talent really does come from anywhere — but that means you've got to put the effort in to find it and to build an environment that’s inclusive for remote workers. If the rest of the team is going to be in the office nine-to-five, five days a week, and you're hiring someone from a different country, what controls are you going to put in place to make them feel like a valued, equal member of the team?

"The second one is to think about personal rapport as well as work rapport. If a team were to be sat around a bank of desks, they’d probably all be chatting about what the weekend was like or what was going on in people's lives.

"In a remote environment, you mustn’t lose sight of that general camaraderie that builds up in a work environment. Think about how you can recreate that in a virtual environment.

"For example, we have regular coffee chats and at my weekly team meetings, everyone is asked about a big event that’s happening in their life outside of work. When things are tough, I think it’s really important that, as a team, we can all rally around and help where we can. That really helps to build a closer-knit team.

"The third one is to ditch the unnecessary and unwanted meetings. As we were implementing virtual first, we actually had this moment where we all looked at our calendars and thought, ‘What are the meetings that are in there that really don't need to be meetings?' From that moment on, we had to be a little bit ruthless with ourselves and really start to question if something truly justified putting in a meeting or could it instead be an async update.

"Those are the lessons I've learned, and I think virtual working provides a massive opportunity for anybody who wants to hire great talent, have a much better work life balance, and have employees are feeling more productive. Those are the real benefits that teams can get."


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