Behind The Scenes At Dropbox Black Ops

“Black Ops” lead Jon Ying works hard to keep the same spirit Dropbox had with 10 employees as it does with more than 1,000.


Jon Ying, 28, has been with Dropbox from its earliest days. Originally brought in by his friend (and Dropbox cofounder) Arash Ferdowsi to do tech support, his role evolved into developing the brand’s approachable, human vibe, including, most notably, creating the “Psychobox” drawing that a user sees if he or she encounters an error page. Eventually he moved into product design, before settling into his current role using all those skills internally to help foster Dropbox’s culture. Senior associate editor J.J. McCorvey interviewed Dropbox’s culture czar at the company’s San Francisco headquarters earlier this year. What follows is an edited version of that conversation.

“Black Ops,” the “internal communications” team that Jon Ying (center) leadsPhoto: Melanie Riccardi

Fast Company: What’s your official title?

Jon Ying: That’s a good question. I think that for the purpose of a talk like this, people have used creative director. It’s weird. I don’t really have one.

FC: Do you have a business card?

JY: (Laughing) No, I do not. I do have a business card, but all it has is my name. It doesn’t have my title.

FC: What about your LinkedIn page?


JY: My LinkedIn page just says Jon Ying, Black Ops team. And then occasionally these other companies will be like, ‘You want to join us as an engineer?’ They have no clue what Black Ops is. It’s so vague and nebulous. But I think that if I were kind of gun-to-head, I would say either creative director or lead of Black Ops, probably. Something unclear.

FC: Black Ops?

JY: At Dropbox we call what I do Black Ops, because it’s kind of this secret wing that accomplishes whatever needs to be done at the company. It amounts to connecting people, keeping them informed and inspired and, lastly, keeping them really happy. I focus a lot on what at other companies would be called internal communications, taking Dropbox’s story and translating it for Dropbox employees.

FC: Tell me about how you keep people connected.

JY: The most visible thing that we do is All-Hands, which we do every week. That is a much more aggressive frequency than most other companies, but we think it’s extraordinarily important for us to make sure that everybody has a good sense of what the company’s up to and why we do it.


With an All-Hands, what you’re basically doing is reciting a lot of facts and then of all those facts, you want everybody to remember, like, five bullet points. You want them to retain that. There are different ways you can do that. There’s copy/paste a bunch of crap onto a PowerPoint and just flip through slides and you hope people remember it, or you can put a little bit more effort into it and make it something really special. That’s kind of what it’s all about. How can I just make this not boring? That’s basically the mandate that I give myself when I’m working on a project like that. It’s the same thing for Dropbox in general, right? It’s just file storage. How do you take something that’s so cold, that’s so tech-heavy, and make it something that people are happy about?

His recognizable Dropbox illustration, “Psychobox” appears on any 404 Dropbox page.

FC: With 1,000 employees, how do you make everyone feel invested in Dropbox’s mission?

JY: When we started out as 10 people, implicitly every person owns or is accountable for 10% of the company’s total impact. When you’re at 1,000 people, you can’t really use that status anymore, but what you can do is provide people the opportunity to be as impactful for what they’re doing as when you were smaller. We try to make sure that people have as big a say into what we’re working on as we did in the past.

The biggest example of that is Hack Week. Unlike other companies like Facebook and whatnot, which has an ad hoc, one-day or one-weekend hack kind of event, we devote an entire five days every summer for people to explore whatever projects interest them. What’s really great though is that people end up working on projects that deeply benefit Dropbox in some way or another. Critical features like two-factor authentication and even Dropbox for Business, that we launched last year, were employee-driven and not a mandate from staff. Every person working at Dropbox was once upon a time just a user, and for those of us who have worked at this company for so long, we have a very pigeonholed view of what Dropbox should be. So to get this outside perspective—I’ve been a Dropbox user, I’m very passionate about it and these are the things that would make it better for me–it’s really great to give every new person the opportunity to explore that to the fullest, and Hack Week is just such a critical piece of that, just because it’s the celebration of, yeah, you should be able to have an idea and own it and see it all the way through.


FC: Making people happy is kind of a huge mission. How do you approach it?

JY: Part of that is just giving people more ways of connecting with one another. My colleague Russ actually went around the office and did a scavenger hunt of all the different things that Black Ops has done over the past few months. We do events like our annual taco trip and holiday party. We do a musical number every once in a while, like tell the news.

FC: A musical?

JY: Yeah. We even did an origin-story musical. It was like a hyper-fictionalized version of the Dropbox origin story. It was pretty funny.


FC: How does your design background help you in your job?

JY: Design is a super-important part of us communicating messages. We do team-specific swag. So, here’s what we did for Hack Week, which I was telling you about earlier. Likewise, here’s a shirt from Parents’ Weekend. We also have some off-brand kind of stuff, too. Scooter’s Sandwich Shop. We want to give teams a sense of identity and help them feel really proud about what they’re working on. Here is kind of the emblem that we made for our IT department. It’s just kind of all the goods that they have and just help them feel that they have a persona. This is my personal favorite, which we made for the Dropbox legal team. It’s just so badass. And here are these dice that we made for our recruiting team. These are kind of their core principles on the recruiting team. The most recent project that we did though was—so, some of Black Ops work is around some level of social engineering. We might have to talk about whether we mention this one or not.

FC: Come on.

JY: We were looking for a gift for employees at the end of the year that was infinitely more thoughtful than, say, cash. What Black Ops worked on for this holiday season was kind of this catalog and basically people have a budget of how many—we call them diamonds—they can spend. But we ended up just curating a list of different items that we think Dropboxers would get a really big kick out of and made it easy for them to order all of this stuff, and it would just arrive on their desk. And what’s cool is, every one of these items was actually suggested by the leads across the company. It’s a very representative book of what Dropboxers around the world would possibly want.

FC: [thumbing through the catalog] A port-a-potty?


JY: There are a lot of inside jokes. One of the other things about scaling is, if you were to go to the bathroom right now, you would have to wait because we only have three bathrooms for each gender on this entire floor for, like, 700 people. The joke is that people wish they had a port-a-potty. Again, it’s just to make people feel happy, to make this place feel smaller than it is. Can we take all the great things about being a 1,000-person company—resources, perks, great food, etc.—and combine it with all the great parts about being a 10-person company? We want people to know we are thinking about them and it isn’t just a giga-corporation.

FC: What made you go into being people-focused as opposed to being on the design team for Mailbox or Dropbox for people? How did you decide to put your design experience toward making sure everybody was happy?

JY: A big part of it was just kind of being an observer and seeing how the company changes over time. This is the sort of thing I couldn’t have mentally prepared myself for, because I hadn’t been through a company of this trajectory. I didn’t know that people would start losing touch with one another; I didn’t know that information would start vanishing. There are whole pockets of information and email and old docs that are unfortunately, completely lost to us for the rest of time. So my thought process was, how can I turn back the clock or slow it down? A very healthy company, a very happy company produces very healthy and happy products. My line of reasoning was that anything that we can invest into making Dropboxers better results in a better product. And so that’s actually where I started. It was pretty difficult to make the switch because it’s invigorating to make something and ship it out to millions. But to understand that you are still in service of millions of those people, but in the context of people you directly know. The fact that I’m doing this for my friends is actually much more valuable to me.

About the author

J.J. McCorvey is a staff writer for Fast Company, where he covers business and technology.