OutSystems: the journey to a $9.5B valuation

**Dan Lines** (0:00)
Paulo, you founded OutSystems in 2001, and have led it since then as the CEO, bringing the company to a $9.5 billion valuation.

**Paulo Rosado** (0:11)
I was at the verge of bankruptcy about three times.

**Dan Lines** (0:13)
Three times, not anymore.

**Paulo Rosado** (0:16)
It's good now.

**SPEAKER_3** (0:18)
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**Dan Lines** (0:52)
Hey everyone, welcome to Dev Interrupted. I'm your host, Dan Lines, and today I'm joined by Paulo Rosado, CEO of OutSystems. Paulo, thanks so much for coming on the pod today.

**Paulo Rosado** (1:04)
It's a pleasure.

**Dan Lines** (1:05)
Great to have you here. You founded OutSystems in 2001 and have led it since then as the CEO, bringing the company to unicorn status. More than a $9.5 billion valuation in February, amazing. But before we dig into that long journey, I want to give our audience a chance to know you a little bit better and about your background.
So could you take us through your career path leading up to OutSystems?

**Paulo Rosado** (1:35)
My background is in computer science. I have a degree from a top university in Lisbon, Portugal. And then I went to the United States for a PhD slash a grad program. And I ended up by getting a master's and entering Silicon Valley work life. And I worked there for four years. Then I started my first company, my first startup in 97 I sold it in 99
Then I work as an executive for a larger company. And then I decided to start OutSystems in 2001

**Dan Lines** (2:02)
Just a few minor accomplishments. You got your degrees, you sold a company really quick. So a few questions for you there. You come from a technical background, but it seems like you were early on an entrepreneur. Like how did that happen for you? Did you already always know you wanted to be an entrepreneur?

**Paulo Rosado** (2:20)
Definitely not. When I was working in the Valley, I was lucky enough to be in a gigantic project that took about 18 to a lot of people. We were a very large engineering team. And this was when I fundamentally realized the issues of actually releasing code and maintaining code and getting specs, getting to change software in a way that was actually workable.
And so the problem was so big, in my opinion, the time that Java was coming out.

**Dan Lines** (2:44)
Yeah, what year are we talking? This is 90s?

**Paulo Rosado** (2:47)
We're talking, yeah, in the 90s. We're talking in 95 was when I saw Gosling presenting Java for the first time. And man, we did this huge project using the Java language and it was just hard. And looking into the anatomy, then I started my company deploying, building and deploying some of the largest internet and extranet systems like the first generation of cloud software.

**Dan Lines** (3:09)
That's cool.

**Paulo Rosado** (3:09)
And that type of software also has a lot of changes because it's impossible to get the requirements right up front. And so joining all of those experiences, the lack of productivity in the whole software development process, just appalling. And so that was the motivation really for OutSystems.

**Dan Lines** (3:24)
What was the company that you were working at? You were saying you were working in the Valley, right?

**Paulo Rosado** (3:28)
Yeah, Oracle.

**Dan Lines** (3:29)
So we're gonna get into how you founded OutSystems, but I really wanted to ask you, since you're coming from a technical background, what were some of the experiences that led you to say, oh, there's a problem here? Is there anything that happened to you or anything that was like shocking that you knew, okay, something is wrong?

**Paulo Rosado** (3:51)
It's actually interesting because they all go back to the anatomy of technical debt and the difficulty of changing software. One of the realizations, for instance, in my career was the explosion of different languages and paradigms and the frameworks to be able to achieve one solution. And those things, those languages were all dispersed with no connection between them. So only very sophisticated companies could actually track all the dependencies. And the problem was that very early on, and this problem today is like huge, but at the time it was already very big, is that the moment you lose developers, the knowledge goes with them. Because what they leave behind is such a high complex situation in terms of code and in terms of different frameworks that all of those dependency tracking, the intent that was there typically goes away. A lot of it was, my experience is that during, in these three phases of my life, I lost team members fundamentally.