Ahead of SaaStr AI London on Dec 1-2 (See you there!) we’re taking a look back at some of our favorite sessions from our European events. It was so great when Daniel Dines, founder CEO of UiPath, joined us in London as just as UiPath made its rapid evolution from process automation to AI.
The First $175,000,000 ARR at UiPath: How Founder CEO Daniel Dines Built An RPA Giant From Bucharest
Top 5 Toughest Learnings:
- Chemistry Beats Expertise Every Time. Assembling a team of A-players who are domain experts but don’t gel is a recipe for disaster. Chemistry and trust trump credentials. People’s personalities don’t change—hire for fit first.
- You Can’t Build Categories On Purpose. The desire to create a new category is arrogant and will cloud your judgment. Categories emerge when timing, technology, and market conditions align perfectly—you just need to be ready when that moment arrives.
- The Fine Line Between Bold and Crazy. Growing 4x in one year (45M to 175M) won the market. Trying to triple the next year (175M to 600M target) burned $400M and required layoffs. Understanding when to press the accelerator versus when to optimize is the black magic of hypergrowth.
- Purity Kills Products. Customers don’t care about technical purity. The debate over “real” automation via APIs versus UI-based RPA was a distraction. Tools need to work for the job at hand, not satisfy engineering ideals.
- You Can Never Stop Listening to Customers. Even at $175M ARR, when a trusted customer calls to say “you’ve lost touch with us, you’re only chasing revenue,” you need to listen. Customers keep you grounded and focused on what matters.
UiPath’s journey from a bootstrapped consumer tool in Bucharest to a public company that went from $1M to $175M ARR in just four years is one of the most remarkable scaling stories in B2B SaaS. But it wasn’t linear, and it certainly wasn’t easy.
Founder and CEO Daniel Dines recently sat down at an Excel portfolio event to share the unvarnished truth about building UiPath—including the $400M burn that nearly derailed everything.
The Accidental Beginning: From Dictionary Tool to RPA Pioneer
Daniel’s path to founding UiPath was anything but conventional. Growing up in post-communist Romania, he did “currency arbitrage” and started a recruitment company at 21 just to survive. After discovering software development, he spent five years at Microsoft in Seattle—an experience he describes as “good for my engineering expertise but terrible for my life.”
“I left a very colorful Eastern Europe Bucharest to go into the cold Seattle,” Daniel explains. But those Microsoft years taught him how world-class software companies operate and exposed him to some of the smartest engineers in the world during Microsoft’s peak (2000-2005).
Returning to Romania in 2005, Daniel started what would become UiPath. But the product that launched the company? A consumer desktop application that let you click any word on Windows and get a definition pop-up. It required sophisticated computer vision to extract text from any application—complex engineering for what turned out to be a commercial flop.
“It was an engineering gig, very interesting stuff,” Daniel says. “But obviously it was a flop from a marketing perspective.”
The $10,000 Pivot That Changed Everything
The breakthrough came from an unexpected source: a small US ISV doing banking software. They needed just one component from Daniel’s consumer tool—the screen reading technology—to automate teller machines.
“They asked for a license and I thought, how much can I ask this guy? I said $10,000 for an unlimited license. Next day they wired the money. The entire revenue from that other application was maybe $100 at the time.”
That single transaction validated a new direction: building software components for developers. But customers kept asking for something simpler than code.
“They were telling us, guys, it’s very difficult for us to use C# or JavaScript to build process automation. We need something simpler. This is how we turned into low-code, no-code.”
Then came the lucky strike that truly launched UiPath. A large BPO (Business Process Outsourcing) company in India discovered them through a web search. They’d been using a competitor’s tool but found them “really kind of stiffer in their mind, not flexible to customer demand.”
“We went to India for two to three months to do a prototype, and it was the aha moment when we really understood—wow, this is the market we hoped for. We were just kids so far, in a playground. But this is a serious thing.”
Learning to Listen: The Microsoft Engineer’s Transformation
Daniel’s biggest personal transformation was learning to actually listen to customers instead of assuming he knew best.
“I started as a software engineer working for a really large corporation. I was completely shielded from customers—I never met a customer in my life at Microsoft. So I came with the same approach in building this business: I am right and they are wrong. If I bring these new features, they will finally be enlightened.”
That mindset had to change. And it did, gradually, as customers kept showing him what they actually needed versus what he thought they should want.
Even today, as a public company CEO, Daniel spends significant time with customers. He calls many of them friends. And they’re not afraid to be brutally honest with him.
Just last week, one of UiPath’s first customers—a major advertising agency executive Daniel plays tennis with—told him straight: “Daniel, I’m disappointed in what you guys are doing. You lost touch with us. You just go only for revenue, you go to different business units, you don’t help me consolidate what we have.”
“To me, it was a powerful moment when you realize you are on the wrong track,” Daniel admits. “Customers always help you go back to your core roots and building something that matters.”
The Category That Nobody Planned
By 2017, RPA was still barely a category. When Excel did diligence on UiPath’s Series A in early 2017, partner Philip Botteri recalls calling a corporate development person at a large software company to discuss “robotic process automation.” The response? “We don’t invest in robots or robotics. What is this about?”
Six years later, RPA is top of mind for every Fortune 500 CIO. So how did the category emerge so quickly?
Daniel is emphatic: you can’t build a category on purpose.
“I don’t think the desire to make a category is the right approach to build software. I think it’s a sign of arrogance. If you play tennis and you’re a young guy and say ‘I have to win Wimbledon,’ you are not going to win Wimbledon. You just have to go and play for the moment, for the joy of doing things. The mere idea of ‘I want to build a category’ is going to prevent you from building a category.”
Categories emerge, Daniel argues, when multiple conditions align perfectly—what he calls “Goldilocks conditions.”
For RPA in 2015-2017, three things converged:
1. Market Readiness: The BPO industry had matured to the point where they couldn’t squeeze more savings from human process optimization. They were desperate for automation to deliver the 5-7% annual savings they’d promised clients.
2. Technology Enablement: The 2011-2012 breakthrough in image recognition (driven by cloud, mobile phones, and neural networks) could be applied to desktop automation. UiPath leveraged this to recognize every object on a screen—crucial for automating over Citrix and remote desktop environments that BPOs used.
3. Timing: Multiple companies were ready to serve the market simultaneously, creating competitive energy and validation.
“There should be a Goldilocks condition—multiple conditions aligned—in order to build a category,” Daniel says. “It was good timing, and for us it was only about good timing.”
The category name itself—Robotic Process Automation—attracted attention but also drew critics who said it wasn’t “real automation” because it worked through the UI instead of APIs.
“Customers don’t care about purity,” Daniel notes. “This is another lesson, guys. If you aim for purity, it’s the wrong way. You need to aim for something that works. Purity bores everything around it and you can’t do real use cases. Even today I hear ‘it should only be API-driven.’ Then generative AI came along—it emulates people, it’s not API-driven, and it’s so powerful.”
The Chemistry Principle: Why A-Players Aren’t Enough
As UiPath scaled, Daniel had to learn how to hire executives outside his domain—sales, marketing, and go-to-market roles he’d never done himself.
His biggest learning goes against conventional wisdom:
“Go for chemistry versus expertise. I was always under the impression that if you can assemble a team of A-players, highly expert in their domain, this is going to work. It is far away from working. This is a recipe for disaster.”
He points to startup teams where three expert founders who barely know each other are expected to succeed: “No, they’re going to argue to death. It’s a recipe for disaster.”
Chemistry—people who trust each other and genuinely enjoy working together—trumps credentials every time.
“A team with people that trust each other and have chemistry and like to work with each other is the best you can hope for in life, in software, in product, in everything.”
Initially, UiPath’s culture naturally selected for this. Daniel hired “really nice, crazy people—sometimes their first job, people that were in their own words ‘corporate fugitives’ who wanted a different experience. It worked. It was magical. At 10pm our office was full—you could see hundreds of people working, drinking wine, being immersed. It was one of the most beautiful experiences.”
But then he started hiring “the experts,” and things broke down.
“People’s personality will never change. This is another big lesson. You see two people that don’t get along—they will never get along. You hire someone with a personality that’s a little bit different, not crazy different, but they change the recipe. It’s like you bring a different ingredient to a recipe—it can change it sometimes for good, but most of the time you destroy it.”
UiPath suffered through “lots and lots—maybe too much” go-to-market leadership changes. “We shot ourselves in the foot with so many changes.”
Now Daniel prioritizes stability and chemistry over credentials. Even when it meant doing the job himself temporarily.
“I had to be the go-to-market leader, having the regional sales leaders under me directly. It’s a freaking hard job—you have to go into all the sales forecasts and calls. I wanted to get out of this, but if you get out and you don’t have the right person, you lose touch with customers, you lose trust with the teams, you create a lot of unhappiness. You basically create dissonance in your company.”
The Four Pillars of UiPath Culture
When UiPath started seeing real scale, Daniel and his co-founders were inspired by Netflix’s famous culture deck. But they didn’t want a long list of generic values like “candor, honesty, openness, flexibility.”
“I had an inspiration at some point and said to myself, let’s reset this exercise and start with just one thing: What’s the most—if there is one word that describes us and our culture, what should that word be?”
The answer: Humble.
“I realized we were there because some of our competitors were arrogant. That was one of the biggest reasons they let a small company out of nowhere steal their lunch—because they were arrogant. So I said the opposite of arrogance is probably what works best.”
But humility alone isn’t enough. Daniel defines culture as an operating framework—values you aspire to, that filter your decisions and interactions, not something you fully embody.
“To me, culture is more like a framework of operating. You aspire to be something. You filter all your decisions, all your interactions by your values.”
The other three pillars emerged to balance humility:
Bold: “You need to be bold in life because if you aspire for little things, you’ll achieve little things.”
Fast: “The fastest company will always create the biggest impact.”
Immersed: “I don’t like work-life balance. This is a stupid thing. You have to be immersed and stay immersed in your life or your work as much as it’s working. But at some point you’re exhausted and you get back to the other thing and immerse in the other thing. This is how I see a good way to conduct your life.”
Humble, Bold, Fast, and Immersed. Four words that captured how UiPath operated—and would operate through the hypergrowth ahead.
The $45M to $175M Moonshot That Won The Market
By 2017, UiPath was finishing the year at $45M ARR—third place in the market behind two larger competitors doing maybe $70-80M each. The competitors were growing about 50%, which would take them to $100M+ in 2018.
Daniel knew the RPA category was about to explode. UiPath had been essentially cash-flow neutral through most of its existence. But this was the moment to go all-in.
“I felt it was huge—it can absorb, we can take a much bigger risk. The biggest company will get the lion’s share of the market. It’s worth pressing the pedal.”
He came to the board with an audacious plan.
“You guys said if you deliver $70M, that would be a great achievement starting from $45M. And I said no, guys. $70M will still be third in the market. We will deliver $200M.”
The board thought he was crazy. Even Daniel admits “everybody thought I was crazy.”
But he went to his regional sales leaders—still reporting directly to him at the time—and gave them the ambitious target.
“To my delight, they were not shocked. They thought I was crazy, but they were not shocked. They said, ‘Give me at least a little bit of time and I’ll come back with a number.'”
UiPath had a concept called “neck on the line” for commitments. The sales leaders collectively committed to $150M ARR.
“Then I knew this is it. We can capacitate the entire sales team to $200M because we will achieve $150M.”
UiPath hit $175M ARR that year (2018), burning $80M. But it wasn’t just about the number.
“We won the market. We got number one position, got in Gartner everywhere. The competition never caught us after that. The gap only increased. It was a very well-timed investment.”
The $400M Burn: When Bold Becomes Too Crazy
Success has a dangerous side effect: it makes you believe you can repeat the magic formula indefinitely.
Fresh off the $45M to $175M moonshot, Daniel looked at 2019 and saw even bigger opportunity. They’d raised a large Series D. They had half a billion dollars in the bank.
“I wanted to go from $175M to $600M. I looked at the capacity and said to myself, we can get minimum to $450M. We can burn $150M—that’s nothing, we had half a billion in the bank.”
But there was a critical difference from the previous year: they didn’t have the right controls in place.
UiPath grew significantly—to around $375M ARR. Incredible growth by any measure. But they burned $400 million dollars to get there.
“And that was not fun because we overhired. That was the moment when we hit diminishing returns, and it could have been very costly for us.”
In 2019, UiPath did something almost unheard of for a rocketship startup: they laid off 10% of the company.
“It was such a big blow to the culture, especially when you’re alone in the market. Nobody was there—’UiPath was firing 10% of their people.’ It was a six-month terrible blow.”
But Daniel describes the timing as fortunate in retrospect. The restructuring happened right before COVID hit.
“We were well better prepared for COVID. Our main competitor at that time was trying to catch us, especially with SoftBank money. They were pouring money into everything—sales, marketing—building a bloated company. Then COVID hit and they’re in a much worse position. We’re nimble. I’d already learned my lessons.”
2020 became an amazing year: 80% growth while cutting costs from $400M to cash-flow neutral—”almost unheard of while growing 80%.”
The lesson? There’s a fine line between bold and crazy, and you need different approaches at different stages.
“This is clearly the black magic of running a company that grows fast. It’s easy to be crazy. When I heard Masayoshi Son saying ‘you are not crazy enough,’ I thought—guys, I am crazy and I can be crazy enough. But I’m going to burn billions of dollars, overrun the market with reps who step on each other’s toes and are unhappy. We’ll burn hundreds of millions, the culture will sink, and we’ll go bust. Craziness doesn’t work. Super craziness doesn’t work. The fine balance works.”
Bootstrap DNA in a Billion-Dollar Company
One advantage Daniel had: he bootstrapped UiPath for almost exactly 10 years before raising the first venture round in July 2015.
“When you bootstrap a company, you need to understand cash flow because otherwise you die. So I was very much cash-flow attentive. It’s part of my DNA. It’s a little bit against my nature to just burn huge amounts of money.”
But he also learned when burning is necessary. He points to Frank Slootman, CEO of Snowflake, as a model for understanding when to press the accelerator.
“He’s an operator—I’m not an operator, it’s a different beast. But as an operator, he describes very well when you have to push the pedal, when you have to increase the reps, how to think about it. He’s an awesome guy.”
Daniel shares a memorable story about meeting Slootman between his ServiceNow and Snowflake tenures. His chief of staff, Brendan, introduced himself.
“Brendan said, ‘I’m Brendan, Daniel’s chief of staff.’ And Frank said, ‘I would fire you the next day. What’s this? It’s a fluffy job. What’s chief of staff? It doesn’t exist.’ He also thinks customer success is a fluffy job and doesn’t exist. To a certain extent I agree with this, but it’s very hardcore thinking. It’s not me, but it’s interesting to watch and learn what you can apply to your own thing.”
(Brendan, Daniel notes, is still with the company.)
The Enduring Power of Humble
Despite the public company pressures, the market leadership position, and the hundreds of millions in ARR, Daniel still starts with humility.
“Humble is very powerful because it makes you listen to others. If you don’t suck all the air in the room, you have to listen to others. Collective intelligence is most of the time better than your own. This is always my style. I very rarely make decisions that I enforce on people. Most of the time they change my mind.”
The power of being humble, Daniel explains, gives you the power to change your mind.
“I make decisions against the group of people I trust very rarely—only when I am 100% convicted this is the right way, when I have the gut feeling, when I tell them ‘Guys, this is against my heart, I will rip my heart if you don’t do this.’ And they will do it.”
But those moments are exceptions. Usually, the team’s collective judgment wins.
“You’re in a very lucky position if you don’t have to invent and reinvent yourself every year and you just listen to the customers. Your job is just to prioritize, understand what are your best customers, what are the best segments, prioritize to their needs. This is what we did. It was simple.”
The Second Act: Returning for the AI Revolution
After taking UiPath public in April 2021—one of the largest software IPOs ever at a $35 billion valuation—Daniel stepped back from the CEO role in 2022. Rob Enslin, formerly co-president of Google Cloud, took the reins as Daniel transitioned to executive chairman.
But the AI revolution changed everything.
By early 2024, with generative AI fundamentally reshaping automation, Daniel saw the same Goldilocks conditions that had created the RPA category nearly a decade earlier. The technology had evolved. The market was ready. And UiPath needed its founder back in the driver’s seat.
In May 2024, Daniel returned as CEO with a clear mission: transform UiPath from an RPA company into the leading enterprise AI automation platform. It was a founder’s return story—but not a typical one. Daniel wasn’t coming back to fix a broken company. He was coming back to lead it through its next major platform shift.
“When generative AI came, I realized this emulates how people work. It’s not API-driven—it’s different, and it’s so powerful when you think about it,” Daniel explains. The same computer vision expertise that had powered UiPath’s early success with screen automation now positioned them perfectly for AI agents that could observe, understand, and act across any application.
The return wasn’t just about technology vision. Daniel saw three critical areas where UiPath needed to refocus:
1. Consolidation Over Expansion. The “go only for revenue” criticism from his longtime customer friend had hit home. UiPath had been chasing new business units and new logos while existing customers struggled with sprawling automation deployments. Daniel’s first priority: help customers consolidate and get more value from what they’d already deployed.
2. Chemistry-First Leadership—Again. The go-to-market churn that had plagued UiPath’s hypergrowth years needed to end. Daniel brought back the chemistry-first principle, prioritizing cultural fit and long-term stability over résumé credentials. Some of the “corporate fugitive” energy from the early Bucharest days needed to return.
3. Fast Immersion in AI. While many enterprise software companies treated AI as a feature addition, Daniel saw it as a platform transformation requiring total immersion. UiPath would rebuild core products around AI agents, not just add AI capabilities to existing workflows. It was bold—the same boldness that had won the RPA market, but now tempered by the lessons of the $400M burn year.
The strategy is paying off. UiPath has introduced AI agents that can observe human work, learn processes, and automate them—bringing the “one robot for every person” vision Daniel had articulated years earlier closer to reality. The company processes billions of automation tasks annually and is increasingly positioning as the orchestration layer for enterprise AI agents.
“We need to be bold,” Daniel says of the AI transition. “But we also need to be humble—to listen to what customers actually need, not what we think they should need. Generative AI doesn’t change that fundamental lesson.”
The return to CEO also meant returning to first principles. Daniel is once again spending significant time with customers, rebuilding the direct relationships that had occasionally frayed during the public company scaling years. He’s personally involved in product direction, ensuring UiPath’s AI agents work the way customers actually work—not the way engineers think they should work.
“The biggest learning in my journey is that you can never stop listening to customers,” Daniel reflects. “Whether you’re bootstrapping in Bucharest or running a public company, whether you’re building RPA or AI agents, that doesn’t change. Customers always help you go back to your core roots and building something that matters.”
For founders considering whether to return after stepping back, Daniel’s advice is characteristically direct: only come back if you’re genuinely needed for a fundamental platform shift, not just to fix operational problems. And if you do return, bring the humility to know you’ll need to change and adapt again.
“People think founders return with all the answers,” Daniel says. “But I’m learning just as much now about AI and agentic automation as I was learning about RPA in 2015. The difference is I now know that chemistry beats expertise, that categories can’t be forced, and that there’s a fine line between bold and crazy. Those lessons apply no matter what wave you’re riding.”
The AI revolution is still early. But UiPath, with its founder back at the helm and hard-won lessons from scaling to $1B+ ARR, is positioned to play a major role. Sometimes the second act is about applying everything you learned in the first act to an even bigger opportunity.
Top 5 Biggest Mistakes:
1. The $400M Burn Year (!). Trying to triple revenue (175M to 600M target) without proper controls after successfully quadrupling the year before. Sometimes you need to consolidate before accelerating again. Cost: $400M burn, 10% layoffs, six months of cultural damage.
2. Over-Rotating to Expert Hires. Abandoning the chemistry-first principle in favor of hiring domain experts who didn’t fit the culture. “We shot ourselves in the foot with so many changes in go-to-market.” The lesson: chemistry beats expertise, every single time.
3. The Engineering Purity Trap. Initially resisting customer requests because they didn’t align with technical ideals. Spending years building features engineers thought customers should want instead of what they actually wanted. “I am right and they are wrong—if I bring these new features they will finally be enlightened.” That mindset cost years.
4. Losing Touch With Early Customers. Getting so focused on new business and revenue growth that long-time customers felt abandoned. “You lost touch with us, you just go for revenue, you go to different business units, you don’t help me consolidate what we have.” Even public companies need to stay connected to their base.
5. Not Understanding Scale Early Enough. As a software engineer, Daniel “never understood the idea of scale in an enterprise. You can make prototypes or little products that help individuals, but scaling across an enterprise is a freaking different thing.” Learning this lesson faster would have accelerated the early years.
From a dictionary tool that generated $100 in revenue to $175M ARR in four years to a public company navigating the AI revolution, UiPath’s journey shows that hypergrowth requires equal parts humility and boldness—and knowing which one you need at any given moment.
“Be humble when you have the courage to be bold,” Daniel says. “People will take you seriously.”
And sometimes, being bold means coming back for a second act when the next platform shift arrives—bringing all your hard-won lessons with you.
