This week Adam is joined by Michael Grinich, Founder & CEO at WorkOS. Michael shares his journey to build WorkOS, what it takes to cross the Enterprise Chasm, and how he’s building his sales organization for growth.
Michael Grinich: When I was an undergrad in college at MIT, I met a bunch of the folks that were working at Dropbox early on. And this is when Dropbox was pretty small. They were like 50 people, or something. Dropbox was started by MIT alums. So they would come to campus, and come to the recruiting fair, and throw parties, and stuff like that… And I ended up spending about six months working at Dropbox, doing some mobile engineering there and building stuff. This is back in 2011. So the company was just starting to grow faster. I think when I went back to school, it had like doubled in size. And the thing I really thought about when I was there - it was not just the mobile app, but how Dropbox was getting used by companies, really businesses, and the positioning we had against other products like Box. We’d actually hired a sales guy from Box back then, and just started thinking about why is it like Box is winning in these business contexts when me and all my friends used Dropbox and it was clearly a better product.
So I thought about that a little bit, but obviously not too much. I went back to school, graduated, and then after graduating, I had been working on this email project. It was actually like my capstone project in the computer science department. So the codebase was there… And it was this thing to synchronize email and build data kind of visualizations on top of email. And I’d always wanted to build an email client. I felt like the email client is sort of the view into the database of your life. At MIT everything runs through email, and I was just like obsessed with email clients.
And so I started this company to try to rebuild Outlook or Gmail with a much more modern take. And to build something that’s really fast, and elegant, easy to use, and something hopefully that would help people communicate and get their job done a lot better. So I figured if you can help people communicate faster, help people kind of structure their thinking better, and help teams work better together, you have this huge effect on productivity, and it’s a high-leverage thing you can do.
So I started working on that, took that codebase, and that became the core of the mailsync engine, and then built this app on top of it. And we obsessed around the design. Really obsessed around the experience of this app. I spent like three weeks looking at fonts, just typefaces – because email’s all text, right? The interface has mostly fonts. Working with a couple designers that – I really, really loved that time working with them, on every single individual icon.
I hired a musician that did sounds for video games, and went to their studio for a couple days and just listened to like notification mail sounds that we were going to put in the app… Because the new mail notification sound you hear all the time. So we really went deep on this, right? Like we went really, really deep on making the experience great. We did all this amazing engineering to make it extremely performant on multiple devices. We had everything from MacBooks to like little Surface tablets, underpowered, that we were making sure it rendered properly, and worked offline.
So anyway, we obsessed around the design of this product. We launch it, and people love it. And it was also open source. So developers loved it, it became a top project on GitHub, and we got all these people signing up. And I had just gone through the Dropbox playbook, right? Build a great experience, that people really like, that’s really useful, put it out there in the world, and people will start using it at work, as well as their personal life.
[07:46] So we started getting users everywhere from like NASA, to Uber, to Facebook, to the city of Minneapolis… Every single kind of imaginable type of user was just downloading it, signing in and using it. And the playbook I had was like “Hey, do the same thing as Dropbox. Just go find the organizations that are adopting this and we’ll sell it to them.” It’s kind of the bottom-up freemium type of business model.
And what happened is a few years later, as we started getting this adoption, I would go in those companies, like Uber, for example, and say, “Hey, there’s 100 people here using Nylas mail. Let’s get you guys on a team plan. Let’s get you to pay for it for the whole organization.” And this was the first time I really learned about any of these things around enterprise features. I had never talked to like a person in IT before that, that type of moment. And what I realized is the same thing that was constraining Dropbox’s growth back then, I was starting to have as well, which is that you could get this amazing adoption and really product-market fit, with the end users signing up and using the product, and using it every day, in many cases… But when it came to actually commercializing and building a business around it, there was this totally different audience, which was the IT admin, or the procurement team, and they didn’t care anything about the design of it, or the fonts, or the sounds I’d put in it, or why users liked it. They pretty much said that they can’t use it unless it had all these seemingly obtuse enterprise features. And in some cases, some organizations actually shut it down. They didn’t know people were using it, and after they’ve learned about it, because it wasn’t enterprise-ready, they shut it down.
Ultimately, this meant we didn’t commercialize that product successfully. We got some people to pay for it, but it really wasn’t growing in that means… And we’ve found that “Hey, in order to actually build this enterprise stuff, it’s going to take an incredible amount of time.” And during that moment, I actually went and talked to friends of mine working at companies like Asana, or Slack early on, and they were all building this enterprise stuff. They’d kind of stopped working on the product features.
So we ended up just fully open sourcing it, shutting it down, pivoting the company… Nylas is still around, and doing well, and growing… But that idea of building a mail client essentially stopped. That died. And I took some time off, and when I was really trying to think about what to do next, I just kept coming back to this problem. I was like “Why did we build the product everyone loved it?” I still talk to people who say “I used that app, it was really great. I really loved it.” Why did we build the thing that everyone loved, but that wasn’t enough?
Paul Graham famously has written and said “Make something people want. If you do that, everything else will take care of itself.” And it obviously didn’t. There was this missing step. And I realized that getting product-market fit - it’s necessary, but it’s really not sufficient to building a business. And if you don’t think about the business side, you don’t really think about how you’re going to commercialize, and who is the buyer, you get stuck. And it might be in year one, it could be in year five… You might be able to squeeze through for a little while, but ultimately, you’ve got to figure out how to go to those actual commercial buyers and satisfy them.
And what I realized was – why WorkOS exists is all this stuff that you need, you can really put it into a software layer. And that’s what we’ve done. So things like authentication, and user management, security features, things like audit logging… All this kind of under-the-hood stuff that IT admins need - it’s pretty complex to build, it turns out. It takes a lot of time, you have to have really good engineers to do it… But the features at Dropbox that they ended up building for enterprise are the exact same stuff that Slack built, it’s the exact same stuff that Asana built. People just kept doing it again, and again, and again. And so I was like “Hey, what if I could take all these features and turn it into a product, kind of like Stripe, or something like that? …they’ve done that for payments, but let’s do it for enterprise stuff.” And that’s WorkOS. That’s the idea.
So I’m not clairvoyant, or anything, I just looked at the hard thing that everyone was doing, the hard thing that I had struggled to do at my first company, and then said, “Hey, let’s just kind of go a couple notches down the abstraction chain and solve this from an infrastructure perspective for everyone.” And it turns out we were so far not too wrong. People are using it, and it’s helping people… But I kind of stumbled into this world of infrastructure for enterprise apps really through building an app myself.