What it’s like to come back to Dropbox, according to our “boomerangs”
Over the course of last year, we had a grand total of 54 “boomerangs” at Dropbox. Boomerang is HR lingo for employees who leave the company and come back after a stint elsewhere — whether that’s another company, further education, or even starting their own businesses. It lends itself to a unique experience that we wanted to learn more about, so we chatted with a few boomerangs from across Dropbox history.
There were some consistent themes across all five conversations — notably, that Dropbox culture was a big reason why people seem to come back. Whether it’s the way we’re investing in our tech stack or the collegiality of how we work together, these Dropboxers felt like there was something special that warranted a second act.
Trying on other gigs for size
Those we interviewed had various reasons behind their departures. For some, it was the desire for an in-office experience; for others, it was a return to startup roots. In most cases, the boomerangs we spoke with didn’t necessarily regret leaving. They all noted that they were in a fortunate position to be able to come back to Dropbox, but most felt that they learned something worthwhile from the experience.
Said Chief Privacy Officer (Legal) Will Yoon, “Curiosity is a very important thing to cultivate, and there aren’t many real mistakes you can make in your career. If you leave and try something new, that means you have more data. I don’t regret leaving — I learned a lot about myself both in terms of limitations and strengths, and I’m better today and a stronger contributor at Dropbox having experienced it.”
Another Dropboxer from our Finance org felt that leaving the company gave him fresh perspective on what other opportunities were out there. And ultimately, it made him appreciate Dropbox that much more.
For HR Business Partner Natalie Romak, when it came to leaving, it was easy to chalk up restlessness to needing a change of scenery in terms of work. It was mid-2020 and she’d just moved to New York only to be confined to her apartment due to the lockdown. Reflecting back, she realizes that she just needed something to change — and her job felt like the most viable option at the time.
The draw to come back
One of our boomerangs on the EPD side said that it was our tech stack that drew him back. A brief stint at another tech company proved not a great fit — notably, they “don’t write things down.” He found himself online 12–14 hours a day because he was working with folks in both Singapore and Spain, so it felt like a game of “hurry up and wait.” He’d change a few lines of code, but would have to wait to hear from other teams before he could move anything forward — he was also taking follow on requests late into the night, and didn’t feel that there were great boundaries between work and personal life. Ultimately, he saw that “there was a very clear difference in terms of how Dropbox chooses to operate their culture.”
Rachel Bycer, Learning and Organizational Development Lead (People team), was originally not so sure if Virtual First was going to be the right fit for her. But ultimately, it was part of what drew her back here. “When I was still at Dropbox, I was facilitating Virtual First trainings — I ran something like 35 webinars on Core Collaboration Hours (CCHs) in a single month! And yet, I hadn’t seen the real value in things like CCHs until I left and saw the huge absence. It says a lot about the way that Dropbox feels about its people. These practices are rooted in well-being and creating work/life balance — it comes from a place of actually trying to make work human.”
She’s now happy to be back at Dropbox and is living the remote work lifestyle to the fullest down in sunny San Diego. These days, facilitating Virtual First workshops is that much easier. To use her words, she has “drunk the Koolaid.”
So… what was it like to return?
Almost all boomerangs felt that the transition back was pretty seamless and Dropboxers were very welcoming. For some, they even had formal onboarding for the first time. Natalie said, “It felt like going home after being away for a while. Everyone was so welcoming, and things were familiar in a way that made it easy to ramp up really quickly. I’d only been gone for seven months, but things had still changed enough that there were new people to meet and things to learn.”
Will even had his own special returning moment with our CEO: “I was eating lunch with the Droplets and Drew saw me, and he came over for a hug.”
When one Dropbox alumna from the Finance org was first thinking about returning, he wondered if it might feel a bit awkward to re-meet co-workers. But, people were very welcoming and excited to have him back, and within a week it felt “back to normal.” In his words, “Every company claims to have a great culture, but even when I left I knew I was going to miss this place. After seeing how things operate at a different company, I realize just how hard Dropbox culture is to replicate — it’s really special, very collaborative, very inclusive… and that drew me back.”
Several folks who’ve boomeranged have even teamed up to create a Slack channel to share their experiences and support one another.
Advice from an HR Business Partner
Quoting her in her capacity as a boomerang, we asked Natalie if she had any advice for someone who found themselves in a similar position — having left, and feeling curious about coming back.
“It can be a weirdly personal decision to return to something that you’d decided to leave,” but “it can be humbling.” All in all, Natalie feels like it boils down to going with your gut. For her, at the end of the day it’s been great to be back, and she “can’t imagine having made a better decision.”
Whether you’re looking into working for Dropbox for the first time or the fifteenth time, you can find job openings here.
