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It is only fitting that Sylvie Veilleux’s current adventure finds her wandering the backroads of the continental United States, cruising across America’s highways in search of her next stop. It’s an odyssey that’s reminiscent of her career path: From a start-up, to Apple, with a pitstop in financial services in between, before finally landing at the powerhouse that is Dropbox as its CIO, Sylvie’s career has been anything but linear.

“As an individual, I can get pretty bored easily. And if there was ever a moment that I felt bored, that’s when opportunities came to me. I love adventure. I love being challenged. I love being busy. And if I can combine all those things together, then why not? It’s been quite fun. This last experience, where I’ve been working virtually in an RV, is just another place that I’ve done something so new and different that’s kept me going.”

While Dropbox is known for its file-sharing prowess, the company, like Sylvie, has expanded its horizons and its footprint in order to aid distributed workforces. On this episode of IT Visionaries, Sylvie discusses her personal journey, the work she’s doing now at Dropbox, and why Dropbox is proving that remote work is here to stay.

Main Takeaways

  • A Remote Worker, Living in A Virtual World: The COVID-19 pandemic has allowed companies to be more agile with their workforces. Just because your team is distributed, doesn’t mean simple company values like culture and team building don’t matter. 
  • Time to Unplug: Remote workers shouldn’t be accessible 24/7. Sure, an employee has the ability to be connected to their device at all times, but that does not mean the company should exploit that. When utilizing a remote workforce, find ways to allow employees to disconnect from the company on their days off so they don’t feel required to check things such as emails, or answer calls.
  • Ready, Player One: The ways employees and teams meet in the future will change from the way they are meeting today. CIO’s and technology leaders need to constantly be evaluating the technology they use amongst their teams. This includes taking a hard look at it if it makes the overall experience better for the employee and if it’s not, finding a better solution.

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For a more in-depth look at this episode, check out the article below.


It is only fitting that Sylvie Veilleux’s current adventure finds her wanderingwondering the backroads of the continental United States, cruising across America’s highways in search of her next stop. It’s an odyssey that’s reminiscent of her career path: From a start-up, to Apple, with a pitstop in financial services in between, before finally landing at the powerhouse that is Dropbox, Sylvie’s career has been anything but linear.

“As an individual, I can get pretty bored easily. And if there was ever a moment that I felt bored, that’s when that opportunities came to me. I love adventure. I love being challenged. I love being busy. And you know, if I can combine all those things together, then why not? It’s been quite fun. This last experience, where I’ve been working virtually in an RV, is just another place that I’ve done something so new and different that’s kept me going.”

While Dropbox is known for its file-sharing prowess, the company, like Sylvie, has expanded its horizons and its footprint in order to aid distributed workforces. On this episode of IT Visionaries, Sylvie discusses her personal journey, the work she’s doing now at Dropbox, and why Dropbox is proving that remote work is here to stay.

As a virtual-first company, the prospect of the CIO working remotely wouldn’t normally yield a second glance. What is a shock is how Veilleux has taken that mission to the next level — traveling America’s open roads, courtesy of her RV, only moving when she wants a new backyard. It’s an adventure that she says is only made possible by the tools developed to keep companies connected.

“Working remotely when the rest of the company is all remote helps us do a really great job working together from anywhere,” Veilleux said. “Dropbox is virtual-first. This makes it possible for me to do some great work, and live anywhere I want at the same time.”

Through the years, Dropbox has worked to diversify its portfolio and steadily become less reliant on its file sharing capabilities and more toward becoming a hub for distributed teams. To do this, the team at Dropbox had to focus on how Dropbox can help remote teams streamline their workflow by providing them the tools necessary to create content and collaborate as needed.

But to build this approach, Veilleux needed to first get a feel for the landscape. .

“I’ve been observing what technology and tools we need to have or include in a complete transformation so we can continue to have productive teams and we can maintain our culture,” she said. “For me, it’s not that complicated because we have great products, but everything else that we use to support the business doesn’t have that same experience. So we’re thinking about how we bring technology to people in this virtual-first [world] and I’m living and breathing it every day. So I get firsthand experience of what is working and not working.” 

Some of the tools that Veilleux has found to be an essential part of distributed workforces is not only do you need to focus on your collaboration tools, but employees are still going to need a place where they can gather and ideate. Veilleux said it’s an important piece of the remote workforce and something Dropbox has put a lot of time and effort into — even going as far as transforming its current workspaces into “studios.”

“This is a place where we’re all going to collaborate and get to get together as teams, but no longer as individuals working at a desk,” Veilleux said. “The technologies that we’re enabling in those studios are going to help us create connectivity and connectedness between people in studios. And because people are not being able to travel or coordinate the travel with other teams, the technology is going to start going from the studios to the home. So we need to extend our networks to people’s homes and we’re evaluating virtual whiteboard capabilities.”

But extending those networks doesn’t mean bombarding employees or team members with countless messages or emails, and Veilleux was quick to point that out. While team members are connected in more ways today than they have been before, it does not mean they should be accessible at all times of the day and Dropbox has worked to address this.

“We have a thing called an unplugged PTO, which is basically if you’re taking time off, you usually have your phone in front of you and are checking it, but with unplugged, we actually enable an automated process that disables your access on your mobile phone,” Veilleux said. “We’re also looking at other automation capabilities across service management, which include things like bots and A.I., that help automate requests that have gone to desktop support or the finance, all the support functions we’re trying to automate through bots and A.I.”

While Dropbox is a virtual-first environment, Veilleux does see some changes to the model moving forward, including how employees will meet and interact moving forward.

“The technologies that are going to be involved [with remote work], they’re going to change dramatically because you won’t need a conference room for meetings because you’re doing that remotely,” she said. “You won’t need a desk to do your own individual work because you’ll be doing that remotely, but you’ll need spaces where it will help you drive innovation and collaboration, and also maintain a team culture. And we definitely love our culture.”

To hear more about the steps Veilleux and Dropbox are taking to put the employee experience first, checkout the full episode of IT Visionaries.

To hear the entire discussion, tune into IT Visionaries here

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