Dropbox People Ops Leader: Why You Must Focus on How Work Happens, Not Where

Where people do their work has been at the center of raging controversy as companies assess their needs and make decisions to either mandate RTO or keep flexible options like remote or hybrid work. Employees have strong opinions and expectations where they want to work, with their tension mounting when they are told they must do work in a certain location.

But when companies and HR professionals take a people-first approach and ask the right questions to solve workplace problems, it focuses the employee experience on “how work happens versus where,” says Allison Vendt, Global Head of Virtual First and Vice President of People Operations at Dropbox.

“I would encourage everyone to take a human-centered, intentional design approach to ensure that you’re asking the right questions. A lot of what I see happening around the conversation about remote work and distributed work and RTO is we’re often focusing on the wrong problems. It’s not about in the office or not in the office, right? It’s about the kind of work that needs to get done, what work could be best done virtually and in-person, what frameworks need to be in place to ensure success,” she explains.

Dropbox decided to go remote in 2020, spearheaded by Vendt, calling the move Virtual First.

“[Virtual First is] about people over places. Meaning, that the work that we do, the impact that we have, is tied to the people doing the work and the talent that teams are made of, not where they work from,” Vendt says.

Vendt shares the lessons Dropbox has learned with a people-centered approach, with advice for other HR professionals who want to create a deeper, more effective and satisfying work experience for employees.

Expect challenges—You won’t get it completely right from the start

A human-centered and Virtual First approach is a great move for the employee experience, but as Vendt explains, this model has not been without its challenges when starting out.

“The real challenge that we faced is the gravity of the organizational behavior change that was required to transform our entire workforce. Prior to 2020, we were a 97% in-office company. And this was something that involved us having to unlearn traditional work behaviors,” she says.

“It has been a major undertaking to not only set that up initially, but on an ongoing basis, it requires a lot of training, reinforcement, reminders, and tips around how to work in this way.”

One of the ways that Dropbox reimagined work behavior was by implementing core collaboration hours. Vendt explains this as a “regional collaboration, a four-hour time block where employees are able to be available for synchronous collaboration. We needed to train people on what that would look like. Over time, what we’ve learned is, let’s serve up information to our teams when they need it the most.”

“Also, a rule of thumb is approaching [a remote work model] with a learning mindset. This space that work is in right now is changing so rapidly … we’re not going to get it completely right out of the gate, but we’re going to build it together. We’re going to leverage [employees’] insights to help us continue to make this model as effective as possible,” Vendt says.

Track organizational behavior changes

Tracking metrics was a must to see how changing work behavior at Dropbox was going. Vendt says rather than pinpointing a few “specific singular data points to track employee engagement in our Virtual First model, we try to look at the relationship between working in Virtual First and the impact on talent attraction and retention, and productivity. And we also look at things like the impact of specific Virtual First behavioral practices. Are people adopting those behaviors? If they’re not, what are blockers to that?”

Experiment with and fine-tune work practices

Dropbox also piloted and experimented with its new practices, testing how effective the work behavior changes were before rolling them out to the larger workforce. That allowed Dropbox to fine-tune and learn what was working. Testing meeting effectiveness in a Virtual First model was one example of what they were reviewing, says Vendt.

“Approaching with an experimentation mindset is important. And it also enables you to not get too paralyzed to start something. Start small, experiment, pilot, and then see what that yields and then keep moving forward,” she says.

Virtual First doesn’t mean you can’t gather in person 

Even though the Dropbox workforce works remotely, Vendt says the “human connection is still incredibly important and there’s no substitute for being in-person together with your teams. Gathering in person is a core tenant of this model.”

Vendt says teams gather about once per quarter in what Dropbox calls “studios” located throughout the world.

One of the interesting things that Dropbox discovered about team gatherings is that it had to reimagine the support models around in-person gatherings.

“For example, gathering in person is quite a new skill for planning an off-site for teams—a new skill for many. So, we had to develop an off-site planning team to support effectiveness around that.”

Want to hear more about the impact of how work is done versus where? Join Allison Vendt at HCI’s SPARK HR 2025 conference at Lake Buena Vista, April 30–May 2, where HR professionals will hear her full presentation. You’ll also hear about engagement, leadership, and workplace culture from speakers at NASCAR, Chobani, Panasonic, LinkedIn, and more. It’s not just another conference. It’s going to be hands-on, interactive, and a chance to connect with people who really get it. Plus, we’re adding some Disney magic, so you’re going to have a great experience. See you there!

This article is presented in partnership with HR Daily Advisor. HR Query is a Q&A series by HR Daily Advisor that focuses on HR professionals' insights on current HR trends and dives into their personal stories, helping HR peers connect with challenges and opportunities.