The Rise of Remote Work: A Deep Dive into Dropbox's Transition Journey (VIDEO)

The Rise of Remote Work: A Deep Dive into Dropbox's Transition Journey (VIDEO)

Insider Info from Recruiting and Engineering Leaders About Remote-First at Dropbox

In Hired’s Summit, an annual event for jobseekers, employers host panels and events designed to provide insight into and coaching for trends and topics of interest for tech and sales talent. In this panel, get behind-the-scenes stories into transitioning to being a remote work, or virtual-first company at Dropbox.

Intentional Actions

Hello everyone. We are super, super excited to be here, and welcome to our panel. We are all here from Dropbox and we’re gonna be talking about how to get hired at a virtual first company.


Moderator: Gina Nicoletti, Global Recruiting Experience & Optimization, Program Manager

Role & Tenure:

I’ve been with Dropbox a whole six weeks, so I probably won’t have as much to say as the others. I am over recruiting experience here at Dropbox on our recruiting operations team.

Fun fact:

I have one-year-old puppy in the background barking so please excuse her she cannot help herself today

Marcus Mackey, Technical Recruiting Manager

Role & Tenure:

I lead one of our product and recruiting teams, I’ve been with Dropbox for about six years now and in the recruiting space for a little bit over a decade. It’s kind of odd because it’s very rare, just kind of where Dropbox is now, that I’m the least tenured Dropboxer on the panel.

Fun fact:

I’m a huge sneakerhead! I own over 200 pairs of shoes, so it’s an adventure in a small New York apartment, you have to get creative. If you open my pantries you might see a few boxes, the same in any of my cupboards, or where I keep my dishes/shoes.

Eleni Anderson, Head of Technical Recruiting

Role & Tenure:

I’ve been here for about 6.5 years. I lead global EPD Recruiting, that’s engineering, product, and design.

Fun fact:

This is also a plug for some of the amazing Dropbox perks. I had the opportunity to take advantage of the ‘Dropbox Recharge’ program this past fall. It’s a program where you can take up to six weeks off and completely unplug and recharge, so I spent six weeks in Europe.

Thomas Le Jeune, Software Engineering Manager

Role & Tenure:

I’m Thomas, I am an engineering manager at Dropbox. I live in San Francisco I think pretty similar to Eleni, I’ve been with the company almost seven years. I lead a team, a product team of about 8 engineers and it’s going really well.

Fun fact:

As you may hear, I have kind of an accent; I come from France originally. Basically, early in my career I really wanted to become a sommelier, but back then it was not as easy to get hired and to have access to a lot of companies. When I didn’t find an apprenticeship I turned to my other passion, which was web engineering, so here I am today.

So my life definitely could have been very different if I was able to get hired very easily back then.

The History: The Transition to Remote Work at Dropbox


So Dropbox was really early compared to a lot of our peers when putting a strong stake in the ground and declaring ourselves a virtual first company. We announced our intent to go virtual, or remote-first, in October 2020.

While this was during the height of the pandemic, it was still significantly before a lot of our peers, who eventually moved to a virtual hybrid model. 

And I would say, from just a social perspective, people were really eager to go back to the way things were. So in full transparency, we did receive some pushback in the beginning after our remote first announcement. This was from both current Dropboxers and candidates in process at the time.

So now it’s two years later and the world has shifted so, so, so much. Now I can confidently say current Dropboxers and our candidates are incredibly excited about remote first and invested in the experience. 

We have so many candidates who opt into Dropbox citing the remote-first company as one of the main reasons because it’s the work style they prefer. 

Our nucleus shifted from the San Francisco Bay area, where I’m based, to truly distributed. On a daily basis, I probably talk to folks in 10 different states, and across the world.

So, if you really want to work in an office, Dropbox is not for you, and that is okay. But we have found a community of individuals really excited about doing their core work done at home. Then utilizing the Dropbox benefits to be more intentional with the in-person time that we do have together.

Remote-First Sacrifices – an Amazing Branded Office Experience

Like many companies who chose to go remote-first or downsize offices, Dropbox had to say goodbye to some office-based perks. As a work benefit, as well as a recruiting and retention tool. 


At Dropbox, it used to be so much of the employee experience was office-based. If you ever came to the office and had our food, you understand it was very glamorous. It was impressive, with a lot of cool stuff.

In addition to the amazing food, our headquarters had a video game room. We needed to reimagine these perks and replace them with more flexible benefits.

Remote Work Employee Perks at Dropbox

  • We have a wellness benefit allowing employees to spend on anything that supports work from home, including food. 
  • Dropbox provides a bunch of ways to connect virtually and in person. So for example, this past week we had a Dropbox virtual concert. It was super fun plus I had the opportunity to meet my team here in the Bay area.

Remote-First at Dropbox Does Not Mean Silos, or Lack of Opportunities to Connect

It’s important to highlight remote-first does not mean there are no opportunities to connect in person. Once Covid restrictions eased, Dropboxers had access to Studios.

  • Studios are collaboration spaces to use if you have a big meeting, or just simply want to get out of your house. They’re in a lot of our major metros. 
  • We also have a pretty generous budget for travel, so you can still see your team while your core work is at your home. 
  • Dropboxers may expense places like WeWork, or other co-working spaces in their location, as needed.

So recreating our candidate and employee experience remotely was a significant undertaking. But on a broader level, the time we spend together in person is much, much more intentional. We still consider it a really strong competitive advantage to have made the shift so early compared to our peers. 

It appears a lot of our talent competitors are trying to catch up with what we’ve been doing now for quite some time. It’s been long enough since committing to remote-first we can say we’re in a really fantastic place with employee offerings and general engagement.

Starting a New Role in Remote-First Environments


As mentioned, I’ve only been with Dropbox for six weeks and I can say being remote-first has been honestly amazing. I had no idea what to expect, even though my recruiter was awesome and set expectations. 

There’s just nervousness around joining a company where you know, nobody, you don’t even really know how to do your job yet, and you’re joining from behind a screen. My biggest concern was, would I be able to build those connections like you would in the office? 

Six weeks in I absolutely feel I’m not missing a beat. I think the biggest reason is the intentionality Eleni mentioned. We’re committed to remote-first, we know what that means, and we’re driving our work in that direction.

Related: Starting a New Job? 10 Ways to Set Yourself Up for Success

Dropbox’s Transition to Virtual-First; How it Changed Teams


I think the structure of our team didn’t really fundamentally change. But I think it’s interesting you use the word, ‘shape.” It is very interesting as the ‘shape’ of it is what you see from the outside and also what you see on the inside. Effectively, it did change because we now welcome a lot of candidates all over North America. 

Different kinds of candidates bring change. For instance, we now welcome a lot of candidates that don’t fit the traditional Silicon Valley profile. I know it’s been a concern, creating social anxiety for a lot of candidates to say, ‘okay, now I’m not gonna live in Silicon Valley, or big metropolitan areas. How could I get hired into a big company like Dropbox?

We’ve now adapted a lot of our processes. We welcome a diversity of candidates coming from different parts of the world. So it’s really baked into our intention of what we want to achieve. So the team structure has stayed pretty much.

At Dropbox, we know having too many reports may be overwhelming and makes it hard to build personal connections. So we try to prevent that, limiting our teams to five to 10 engineers.

What changed for sure is the connection between people. Before, you would have been able to meet other peers at lunch for instance. Unintentional, informal, passive connections like meeting someone because you stood next to them in a lunch line.

Now we need to be, again, one of the key words we’re gonna use a lot is, intentional. I think we need to really say, how are we gonna keep building these connections? What do we do in order to make this connection? 

So now, for instance, as an engineering manager, I need to really be intentional about:

  • How do I want to lead my meetings? 
  • What’s the best way to prepare for these meetings? 
  • I need to set up a proper agenda. I need to make sure everyone has “the homework” before the meeting. You can’t ‘wing it’ last minute really. 
  • How do we try to, not enforce, but facilitate interpersonal connections, taking into account Zoom fatigue, and off-sites as well. It’s really fun stuff.

Company Policy to Collaborate Effectively

One thing I want to point out the company has done really well to facilitate this. As we’re welcoming a lot of candidates from different time zones, it could really quickly be a mess because if I want to meet with one of my east coast reports at the end of my day it could be a really bad experience for them. It would be really late for them. We don’t want that at all. 

It’s been a really clear policy from the company. As a solution, the company has set what we call ‘collaboration hours.’ It’s a block of four hours shared across the entire North American region.

So for Pacific time, it’s from 9 to 1 p.m. For Eastern time it’s from 12 to 4 p.m. So the goal here is to have one central block where everyone is expected to be there and after that, it’s really up to you. You can start early, you can leave right after. If you have a doctor’s appointment, resume work later. It’s really a mix between discipline and flexibility. I think it really helps to align the entire company with a standardized way to work together.


I love that and it’s something I’ve transitioned to in the last six weeks. It has been super crucial to ensure we partner together. Again, that word is intentional, I think it’s just gonna keep being repeated throughout this conversation. 

Want more, including the Q&A from this event? Watch the whole presentation about working remote-first at Dropbox in this video!

If you’re ready to find a new remote, in-office, or hybrid tech or sales role, sign up with Hired. It’s free for jobseekers!