Why I’m joining Dropbox
Some thinking behind my decision
First things first, the last two years at Shyp have been the best of my career. I joined the company when there was a group of 10 ambitious people huddled inside a small warehouse. Since then, the company has grown to 200+ equally ambitious people. I’ve was lucky enough to have had the opportunity to build the Design Team and define what Design became at our company. It’s been quite the journey, and I owe a lot to Shyp and the team. I’ll be forever rooting for them.
Why did I leave?
Not an easy question to answer and one that is filled with nuance. I’m the type of person that gets uncomfortable if I feel I’m slowing in my personal growth. Every day, I wake up and want to push myself in new ways. A polarizing change in environment was the fastest way to achieve that.
As a designer in tech, there are three environments in which you can work — an agency, a startup, or a big tech company. I’ve yet to do the latter, and I’m ready to experience how design operates within a larger organization.
So, why Dropbox?
The reactions I’ve received when I share that I’m joining Dropbox have been pretty mixed. I’m not surprised by this—especially given the other seemingly more compelling opportunities I had on the table. But to me, the fact that people are surprised I chose Dropbox makes the decision all the sweeter. Let me explain why .
Is Dropbox a dying unicorn?
Dropbox has been straight up written off by the tech press. Because of this, popular opinion is registering the clock at about 10:00pm. Admittedly, this was also my opinion only a month or so ago. But press is a lagging indicator and rarely tells the full story. Yes, the company has had a rough two years. They spread themselves too thin—working on consumer photos, email, file storage, team collaboration, and other endeavors has got to be difficult for a company that isn’t yet Google.
But here’s the deal, Dropbox is turning a corner. While the realignment was surely painful to go through, the company is more focused than ever. This newfound focus is going to lead to big things. Dropbox’s fundamental business is strong, and they’ve generated astonishing yearly revenue with Dropbox Pro and Business. Now, imagine what’ll happen when they double down on what’s already working.
Dropbox is, and has been, an underdog in the tech world. They haven’t yet “won” as a company. But I love underdogs. I’m uninterested in joining a company that has already reached the finish line.
While the future of Dropbox is far from guaranteed, it’ll be so sweet to make the naysayers eat their words. Let’s get it done.
What about the designer attrition?
Yep, there has been attrition on the design team recently. When you see designers you respect departing the company, it doesn’t look good. But I investigated the attrition by speaking directly to people who’ve recently left the company. Don’t rely on the grapevine—just go to the source. I spoke to two of their previous Heads of Design and a handful of other designers. I framed these conversations around gathering the most critical feedback. I wanted the real shit. This backchanneling ensured I had a clear understanding of what I was stepping in to.
After digging in, the attrition is absolutely understandable. There’s nothing more disheartening than to invest years of your heart and soul into a product that shuts down (Carousel, Mailbox). It’s also frustrating when the company has lacked a clear vision. It makes it difficult to prioritize efforts and leads to confusion on the team.
However, the reassuring piece for me was to see that Dropbox is out of the woods on most of this stuff. While shuttering products may lead to some turnover, it doesn’t mean it’s the wrong decision for the company. It was a necessary sacrifice to allow for a more focused Dropbox.
I very much look at this as a fresh start for the company. Onwards and upwards.
The Dropbox Team
Dropbox has one of the strongest teams across the board—hands down. Often designers will solely look at the design team when exploring new jobs. That, to me, misses an essential success indicator. It takes more than strong design to build a strong company. You need world-class engineering, product, and business teams. Dropbox has that.
As I’ve become more familiar with the team, I’m intimidated with their level of talent and intellect. I’ll be working hard to not bring down the average :)
A recruiting process that left me smiling
My recruiting experience at Dropbox was nothing short of amazing. It actually became a significant selling point for me because it spoke to the level of care the team has for people.
I was not an “easy” person to interview. In total, I visited Dropbox five times to speak with as many folks as I could. My intent was to suss out a broad, diverse set of data points on the role and company. I appreciated the team’s patience and welcomeness towards this exploration.
On my final visit, they blew my mind. I was chatting on the rooftop of their office with another design manager. As we wrapped up, I noticed a bunch of folks from the design team walking out with champagne in hand, appearing to be in full party mode. I asked what they were celebrating, “Did you just have a big product release?”
Nope, this is for you.
Seriously, mind blown. I hadn’t even accepted the offer yet. What a phenomenal way to show you truly want someone on the team. I left their office that day with a huge smile on my face—Dropbox was starting to feel like home.
The icing on the cake was this little pink box that greeted me on my apartment doorstep that night. No shipping label, nothing. Just a small smiley face tapped to the outside. I eagerly opened it to find a cupcake kit with a letter-pressed note from Dropbox expressing their excitement about the potential to have me join.
Cupcakes hold a significance to Dropbox. The company has five core values, and the fifth value is just a picture of a cupcake. It represents delight and that’s what they strive to bring to their users. What a way to end things.
I’m beyond excited to be leading the design team for Dropbox Pro and Small Business. Essentially, this team is focused on individual consumers and smaller companies that signed up organically. We’ll be building stuff that both increases value for paying users and entices non-paying users to upgrade.
This is a distinctly interesting challenge as almost every Pro user I’ve spoken to has upgraded because they “need more space.” But to me, that’s just scratching the surface of opportunity. Looking forward at the changing paradigm of files and data storage, Dropbox will need to adapt and find more ways to provide value and utility to its customers. This is a deeply exciting problem to solve.
This is as much as I’ll say for now, as I still have an outsider’s perspective on things. I’ve got a lot to learn — my first day is tomorrow.
 I spoke about Dropbox as a company, past and present. The stuff I wrote is truly my opinion. As someone who is still on the outside looking in, my current view may be naive. I hope to learn much more in the coming weeks.