Dropbox

“Probably, like, the most famous example of an organization that, like, maybe didn't get sales religion as quickly as they should have would be would be Dropbox.”

“As I was leaving Dropbox, the finance team looked at our metrics and saw that each growth PM was bringing over a million in ARR per year just from all the experiments.”

“Interestingly enough, Kim Scott was at Dropbox for a short period of time. So when I joined Dropbox, she was actually on my interview panel and we overlapped for three months. And she actually workshopped that book with our team before, or before she published…”

“Dropbox was known for this. We would hire a ton of like really smart people that had never done sales and had them do sales.”

“Our team at Dropbox moved a ton. Actually, we started marketing. We actually then report into the revenue org with sales, and then we finally moved into product because we realized so much of our revenue was that product growth motion happening in the product …”

“That company X might be at Dropbox, where every .5% improvement and conversion makes a difference, but if you're early stage, it doesn't matter, and you need to actually think bigger.”

“Back in 2013 in tech, growth was kind of like this dirty word and revenue was a dirty word. And so we were like, oh, a good product should sell itself.”

“I think a learning was that we just started our sales motion and our enterprise a little bit later than we should have. And a lot of competition caught up to us.”

“Just because you got to level four on your main product doesn't mean product market fit is free on all these new products. Right. And you've been inside Airbnb and I've been inside, you know, Dropbox and Twitter, like getting new products to be successful is h…”

“It's really scary when two founders get together just to start the startup and don't have any history. That, that massive red flag. Sometimes it works out. Like in the case of Dropbox, Drew and Arash, you know, both went to MIT, but I think they didn't know ea…”

“Through the six months I was there, I would ask, I'd ask one question, like multiple times a month to, I broke kind of the early beta users into a bunch of different lists, and I'd ask, which best describes you? I like to be among the first to try cool new tec…”

“To me, I think it's a great accelerant when it's already working, but it can't fix it if people don't want to talk about your product.”

“You try to build multiple products in a functional org, but then you know, you lose accountability because people are like, well, I'm spinning a lot. I'm trying to make Dropbox work and I'm trying to make mailbox work and I'm trying to make paperwork and all t…”

“Every time you move up a league, your reward is a stronger and better and opponent and potentially a more on level playing field.”

“I felt like I had done that. That's what, that's a big part of the problem that led to a lot of this chaos at the end of the chapter two, where I was like, oh man, I'm on this, I'm doing stuff, but I'm clearly not setting the right direction or people are conf…”

“I think burnout is the biggest thing that will sort of kill you.”

“I killed carousel, killed mailbox. Went all in on productivity. To some extent that was an easy, a relatively easy decision because most of our subscribers, you know, 80% of people paying for Dropbox were using it at work”

“They were faster. Your company grows and rises. The easier it is for new people in the company to think they hit a home run instead of You know, starting on third base. And so a lot of complacency and entitlement and preoccupations with things other than our c…”

“We put this video on dig and read it and our beta waiting list went from 5000 to 85,000 people overnight.”

“You need to understand what game you're playing. And you need to get good at the micro. It's not that like the meta is more important than the, it's like you need to do all three at the same time. And so that's really the hard part.”

“The only thing that really worked to even just like keep the lights on was basically giving people like double promotions so that they could justify the, you know, someone who's a director at company X, like making him a VP at Dropbox. And then you had to do t…”

“When we launched dash, we usually do like a press Thing. You know, conventional press, tech press, we got like almost no coverage for it. And yet all the stuff we did on social or going direct was like way, way, way more impactful.”

“Steve Jobs was like on stage in 2011 announcing iCloud, calling out Dropbox by name as something that will be viewed as archaic.”

“And then it hit the top of Hacker News for two days, which doesn't, I don't think it can really happen anymore.”

“The products launched, but you would never be able to look at our numbers and see when that happened.”

“In 2007 too, like we, instead of hiring PR firms and buying AdWords and stuff, we were creating these like viral videos and we were using math, you know, using math from epidemiology to create these viral loops. In a lot of ways, Dropbox took that transplanted…”

“Many in SAS SaaS productivity have this sort of sophomore slump where you have a super successful first product, but then it's challenging to build like the next, you know, the next platinum album. Right. So, you know, Dropbox has fallen into that category. Yo…”

“Everybody's got strength and weaknesses, but as CEO, like, you know, both your strengths and your weaknesses are massively amplified. And a lot of blind spots in your personality can become huge cultural dysfunctions in the company.”

“Going from, you know, maybe seven, six million valuation in 2007 to twenty seven million in 2008 to then four billion valuation in 2011, you know, being on magazine covers, just that whole experience was wild.”

“There's a big time lag where between when these products launch and when they actually have an impact, because often it's not so much the existence of the product or its availability, it's the sort of Constant bundling or the constant iteration or, you know it…”

“One thing that happens when you're a founder and your company succeeds is your identity is fused with the company. And so it's easy to get in a situation where you only feel good if the company's, or however the company's, how you feel is how the company is do…”

“The problem is that every incumbent is gonna copy your product, they're gonna bundle it with their platforms, and then they're gonna kill the economics.”

“One of the best predictors of an exec continuing to scale It's not just how, what they know or what they can do, but like the extent to which they can actually like be aware of their failures and not blame or dismiss things.”

“Now, for example at Dropbox, over 50% of acquisition comes through sharing.”

“I actually had that happen to me at Dropbox not so long ago. Somebody reached out and they're like, oh, I look like it was like some page and activation flow and they're like, oh, I love this page. This is so cool. I love what you've done here. And like, I'm g…”

“Most of growth loops spin out a their ability to produce meaningful results for you within the first five to six to seven years.”

“So for example, for Dropbox, they do have a product principle called Cupcake. For Snowflake, they have something called Superhero. I mean, the names could vary, but the meaning is exactly the same. I mean, it's all about bringing joy to the customers.”

“However, what I can say, it's on par with benchmarks of other B to B SaaS products that I've ever worked at. And I worked with Miro, Dropbox, SurveyMonkey, Netlify Amplitude and others.”