A day in the life: Engineer onboarding at Dropbox

We’re Adam Hood and Brian Amaratunga—two senior software engineers who joined Dropbox in 2021 as Virtual First employees. This means we spend most of our time working remotely, with physical studios reserved for in-person collaboration.

When Dropbox became a Virtual First company in October 2020, it also meant reimagining the onboarding process to ensure new employees still had a high-quality experience—similar to what they would have gotten before in person. As two recent hires in Engineering, Product, and Design (EPD), we wanted to share our experience of what virtual onboarding at Dropbox is actually like. 

Adam: I’m an engineer on the Business Space Experience team. Our goal is to improve the workflows of teams that use Dropbox. My story with Dropbox goes back to my college days in 2015 when Dropbox would recruit very heavily on my campus. They would hand out Dropbox t-shirts like they were problem sets, and I suspect that at least a quarter of the undergraduate population had one, if not more. Fast forward to Spring 2021; my job in tech was satisfying enough, but I really wanted to look for ways to grow my career—and I came across Dropbox once again. I’ve always been impressed by their innovation. Early in my career I remember integrating zxcvbn, an open source password strength estimator developed by Dropbox, into a login page that I was developing! As I interviewed with Dropbox, I enjoyed thinking through the tough interview questions—which were unlike any I’d seen before—and I was encouraged by the answers the interviewers gave to some tough questions from me. They really seemed to believe in the company, and were excited about Virtual First.

Brian: I’m an engineer on the Organized Experience team. Our mission is to give our users the tools to keep their files tidy and organized—or, as we like to say, “a place for everything and everything in its place.” I was looking to move on from my previous job in the healthcare software industry, so I made a profile on Hired.com. I was mostly expecting to learn about startups and smaller companies that were hiring, but Dropbox was one of the first companies to reach out. I’ve always heard great things about Dropbox’s engineering talent and culture—and with what I’d read about their vision of remote work, I was very interested in continuing the hiring process. I thoroughly enjoyed my interviews, and the questions felt challenging as opposed to just questions copied directly from LeetCode. In addition, I was impressed by all the engineers and recruiters I spoke with, which made me realize my initial impression of Dropbox was true. Once I matched with a team and learned more about the projects I’d be working on, it was a very easy choice to accept the offer.

Before Dropbox, we both experienced in-person onboarding at other companies, but they were of opposite extremes. Adam had essentially no onboarding at his previous company. Brian was overloaded with classes but had little practical experience early on. But at Dropbox, we found a middle ground. New hires are called Droplets, and have 90 days to get up to speed on our culture, learn various teams' processes, and ship their first small project. Engineers get all the resources they need to succeed without being overwhelmed by information—or immediate pressure to deliver results.

Our first day of onboarding was held over Zoom and led by our onboarding lead Alinane. We were both very impressed. As a group we talked through the Dropbox mission, our values, and business strategy. We also set up our laptops and signed-up for benefits. Spending the day on Zoom was exhausting at times, but our onboarding struck the right balance of being useful and informative without being overwhelming. 

One of the most useful things we received was an onboarding checklist of important tasks and a timeline for when we should do them, be it in our first week or first month. This allowed us to learn more about the company—from senior leadership to our users’ workflows—at our own pace.

The next day, we met our onboarding buddies. Adam was paired with Bozhen, and Brian was paired with Jiayi. They were responsible for helping us get settled—and at first they bombarded us with loads of information. For example, we received dozens of links to various useful resources. We also learned everyone's names and roles—both on our team, as well as the teams we would work most closely with. It was overwhelming at first, but also very helpful to have a fellow engineer as a resource for whatever questions popped into our heads or to guide us through various processes. Our onboarding buddies were always gracious with their time, whether responding to messages over Slack or walking us through our team’s strategies over Zoom.

Since we would primarily be working remotely, one of our top priorities was to set up our workspaces. 

Adam: I was very worried about getting used to the Touch Bar on my new Mac, so the first thing I wanted was a keyboard. Luckily, Dropbox made it easy for us to order gear like this through an internal website called Dropgear! I later added a standalone trackpad and a monitor to my desk. I really love my overall setup at this point.

Brian: I also used Dropgear during my first week to get a monitor and a mouse! There were some issues with the supplier, so it took several weeks to get the mouse, but it took less than a week to get a 34-inch ultrawide monitor from Dropgear—without paying a penny! Dropbox also has something called a Perks Allowance which we can spend on pretty much anything we want (with a few exceptions). I joined a week before the quarter ended, but was still able to use the full amount to get a really nice adjustable standing desk and Steelcase chair.

Onboarding for new EPD hires consists of both interactive video calls and documentation for asynchronous (async) review—meaning at our own pace. There were around five video call sessions over the first couple weeks, each around one-to-two hours, while the rest of the information was documented in Dropbox Paper for us to peruse when we had time. 

This mix of video calls and async learning was our first introduction to “async by default,” one of the key tenets of Virtual First at Dropbox. This means Dropboxers default to sharing information async—communicating via Slack or email as much as possible, and reserving meetings and real-time communication for discussion, debates, and big decisions.

Each video call session was designed to get us acquainted with how Dropbox works on a technical level, both as a product and as a company. We learned about how we use open-source software and best practices for committing and reviewing code. Particularly enjoyable was a talk that introduced the overarching architecture behind Dropbox. It was really nice to get a solid mental model of all the pieces—such as our hybrid approach between a monolithic and service-oriented architecture (Atlas), our async task framework (ATF), and our block storage solution (Magic Pocket)—and how they all fit together.

There was enough information to get us started and show us where to go when we were ready to dig deeper. And it was perfectly reasonable if we didn’t recall everything that was covered; each session was recorded and made available to watch again later in case we needed to refresh our knowledge.

The remaining onboarding sessions were written in Dropbox Paper for us to go over at our own pace. These self-guided lessons included a deep-dive into how our file system syncing and sharing works, and a guide to preparing for our twice-yearly performance reviews. Having so much material available async gave us a lot of flexibility when choosing when to learn and how we prioritized what to learn first. If either of us was feeling Zoom fatigue or needed some time to digest a more complex session from the morning, there was no need to jump straight into another potentially exhausting video call. We could take as much time as we needed and then jump into an async session when we were ready! At the same time, this flexibility allowed us to fit our lessons into whatever schedule worked for us and our managers. This meant we could start working on actual projects earlier in the onboarding process. We even got to ship code during our first week!

Onboarding was also the perfect introduction to another core pillar of Virtual First at Dropbox: Core Collaboration Hours. These are four hour blocks when all meetings are supposed to be held. In North America, for example, Core Collaboration Hours are from 12 pm to 4pm ET. The remaining four hours of the day are meant for uninterrupted deep work—and everyone has the flexibility to work those hours whenever they feel most productive, because Dropbox is async by default. This helps reduce unnecessary meetings and help us make time for what matters most, from deep work and team building to time with family and friends.

We were definitely worried about how we would build connections with our team in a virtual first environment. At our previous companies, we were able to walk up to people's desks or casually grab coffee, but that wouldn’t be possible here. However, with some gentle nudging from our managers, we realized we just had to be more purposeful about building those connections than we would have before.

In our first couple of weeks, we grabbed quick, 15-20 minute one-on-one meetings with our teammates. We shared how we ended up at Dropbox, and heard how each of our coworkers arrived here as well. We were impressed by the diversity of experience of our various team members, who came from all sorts of unique backgrounds, and attended virtual social events to get to know them better. For example, Brian’s team has a weekly virtual board game event where the team gets together to play board games online.

While meeting people remotely was a new experience, our colleagues did a great job of making us feel welcome from the start.

We received our onboarding projects on our second day at Dropbox from our onboarding buddies Bozhen and Jiayi. Adam worked with Bozhen on updating modals in the Dropbox web client to improve the file upload flow, while Brian worked on adding some new naming convention rules to help users keep their file system organized. 

Bozhen and Jiayi did a great job breaking these projects down into well-defined, manageable tasks. They introduced us to the sprint planning processes, roughly estimating the time required and assigning due dates for our work. With our onboarding buddies handling the project planning, we could focus on getting to know the codebase—including the code commit and review process—without the added stress of vague or overcomplicated goals.

Codelabs were one of the most useful resources in our onboarding. These are targeted tutorials that demonstrate how to accomplish different tasks within the Dropbox ecosystem—such as how to create a new API endpoint or how to create a feature gate. We found them to be extremely useful, not just as tutorials, but as reference materials when completing our first projects, ensuring we didn’t miss any steps. For example, Brian was able to ship code his very first week, and used the feature gate codelab to prevent people outside Dropbox from being able to access his work while it was still under development.

Our onboarding projects lasted 6-8 weeks. Brian shipped the new naming convention rules to users during his seventh week at Dropbox! At the same time, Adam helped Bozhen complete the new file upload flow a couple weeks ahead of schedule, enabling the team to start user testing sooner. By this point, we were pretty comfortable with the Dropbox development ecosystem and started working with the rest of the team on other projects. Even though we were technically still onboarding and reading through the occasional onboarding doc, we felt like we were fully integrated into the team.

Overall, Dropbox onboarding was by far the best experience either of us has had. We appreciated the process was async by default—and with so much written down, we really could go at our own pace. It resulted in a very smooth ramp-up period. A huge shoutout to Bozhen and Jiayi for being so supportive through our first few months!

After a few months in our roles, we both started interviewing prospective new engineers and were able to share the positive onboarding experience that we had. Brian became an advocate for our Virtual First team—which is dedicated to ensuring new employees have a successful transition from in-person to virtual work—while Adam became an onboarding buddy for other new hires as his team continued to grow. We like to remind new hires that the three month ramp-up time is dedicated to learning, without the expectation of immediate results, so that by the end they can be more effective engineers.

The days of in-person bootcamps where engineers could quickly build connections with their coworkers and fellow Droplets may be gone. But those days also meant absorbing large amounts of information in real time, which isn’t the best learning experience for everyone. With the shift to Virtual First, we think Dropbox struck the ideal balance between individual learning and community building—empowering new hires to learn and contribute at their own pace, while building strong, human connections with their teams. And if you’re interested in experiencing life at Dropbox for yourself, we’re hiring!