When Olivier Pomel and Alexis Lê-Quôc set out to bridge the divide between developers and operations teams, “cloud” was still considered a ‘toy’ – and most VCs weren’t buying in.
RTP Global recognized the potential and led Datadog’s $6m Series A round in 2012. Today, Datadog is a $30bn+ public company, powering thousands of engineering teams across the globe. From scrappy beginnings to becoming one of the most admired names in cloud infrastructure, Datadog’s journey is a masterclass in vision, execution, and customer obsession.
At our 2023 Founder Summit in New York, Datadog CEO and co-founder Olivier Pomel joined RTP Partner Jules Schwerin for a live fireside chat to reflect on this journey. And here’s how their conversation went.
From navigating early skepticism to scaling a global business grounded in customer obsession, Olivier shares hard-earned lessons on storytelling, staying frugal, and building for the long term.
The spark behind Datadog
Jules: Let’s rewind to 2010. Cloud wasn’t really a “thing” yet and hardly any companies were using it. What gave you the conviction to start Datadog?
Olivier: The starting point wasn’t the cloud, actually. That was more of a trigger. My co-founder and I worked together at a previous company. He ran the operations team, I ran development. We were good friends, but our teams ended up at odds. Development hated operations, operations hated development. Everyone pointed fingers.
So we asked: how do we get these people on the same page? How do we get them to solve problems together and not hate each other? That was really the genesis. It was more about DevOps than cloud, though the rise of cloud gave us an opportunity to rethink the entire stack.
Jules: And Datadog as a name?
Olivier: Well neither of us had a dog! At our previous company, we had an Oracle database that everyone feared. That database was called Datadog17. So when we started working on this idea, we used that as our internal codename. People remembered it. So, we dropped the 17 and kept Datadog.
Jules: In the early days, it was just you and a team of engineers. You’re very technical, and Alexis is very technical. How did you figure out the pitch, especially to customers and investors? My understanding is that early fundraising wasn’t smooth to start with.
Olivier: We split roles pretty early. Alexis spoke with the DevOps community and potential customers. I tried to raise money. But we had a really tough time raising our seed round. Most of the so-called “smart money” – especially on the West Coast – passed on us. I didn’t live in the Bay Area so I’d fly in, take a taxi to meetings, drag my little rolling suitcase up and down Sand Hill Road. Sometimes it rained. Sometimes I’d be stuck in a sad Starbucks between pitches.
At the end of the day, you get all the polite rejections: “too early for us,” “we love the idea, but not the right time,” and “let’s stay in touch.” It was horrible. Especially when we saw other startups doing similar things but with, in our view, less insight doing well and getting huge checks. We were lucky that RTP and Index Ventures co-led our Series A. We were very thankful for the investment from RTP; it put us on the map at the time.
Jules: Do you think those early constraints shaped Datadog’s culture?
Olivier: Definitely. In general, I think constraints breed success. When you know money might run out, you build differently. We built a culture that was thrifty. We’re very careful about money. We’re very careful about unit economics. That’s always been true, from day one, even when it wasn’t considered ‘fashionable’.
The second thing we did, we sought to build a company and a business model that would produce good unit economics at scale. We hear a lot about product-led growth, but I don’t love that term because it implies that sales don’t have a role and that’s very far from true.
What is very true about building a company that’s great in economics is that you need to make sure you have sales and product working hand in hand, and you need to design your business – and your product -around the fact that you can onboard enough of the right customers and grow them in a frictionless way. That way you can have a very efficient business model in the end.
It’s not enough to do it at the sales level. You have to do both, and the two have to be built together. It’s really about company building.
Jules: Any specific frugal moments that stand out?
Olivier: So many. We traveled cheaply, staying in Airbnbs before it was a premium experience. One time, our head of product ended up in an awful place with mold on the wall, Christmas lights for lighting, a door that didn’t close, and a roommate who knocked on his door all night. We moved him to a hotel the next day!
But we weren’t cheap for the sake of it. We spent where it mattered: offices that impressed candidates, good environments that helped us close customers. But we avoided spending money on things that didn’t help us grow.
Jules: And you chose to build a SaaS company in New York… That was unheard of in 2010! Why here?
Olivier: So first off, we lived in New York. But it turned out to be an advantage as we were closer to our customers. That kept us focused. Although talent was harder to find here than in the Bay Area, retention in New York was better. Engineers stay longer versus in the Bay Area, where churn every 18 months is normal. It’s hard to build a strong culture with that. We also hire in Europe, by the way, where the tenures are even longer.
The art of pitching and storytelling
Jules: Along the way, you’ve done a lot of pitches. Short of watching yourself pitch in the mirror, do you have any practical tips for founders who are trying to get better at telling their story?
Olivier: The real key is knowing your business inside and out. That means spending serious time with your customers – understanding what they’re doing with your product, what they’re not doing, and what they think about it. It also means knowing your numbers. When you can speak in detail about usage patterns, churn, expansion – whatever matters for your business – you earn credibility.
That’s your foundation. But there’s a paradox: in the early stages – seed or Series A – you often don’t have customers yet. You might not even have a product. So pitching at that stage is more about pure storytelling. You’re selling a vision with limited data. It’s hard, and you’re kind of making it up as you go.
As you scale, though, you develop a much firmer grasp of reality. You understand what’s actually happening in your product, what your customers experience, and how your business performs. Then the job becomes translating all of that into a story – one that aligns with the facts, but is simple enough for someone on the outside to instantly grasp. And you need to show how today’s reality can grow into something much bigger five or ten years from now.
And honestly, that never stops. Even as a public company, I’m still doing that. We’re constantly telling a story that lines up with our numbers, that makes sense based on what we know today but also points to where we’re going next.
The trick is simplifying just enough. Too simple, and it’s unrealistic. Too complex, and nobody understands it. And if you ever walk out of a VC meeting thinking, “they didn’t really get what we do”… just wait until you meet public investors. VCs might work closely with a handful of companies for years. Public investors might hold your stock for three weeks and cover dozens of companies at once. So the bar for clarity keeps getting higher.
The go-to-market strategy and the importance of knowing your product
Jules: Am I right in saying that, in the early days, you were all engineers and there were no salespeople?
Olivier: Yes, our first head of product also ran sales – and it was very intentional. The way we think about product at Datadog is that product managers aren’t there just to “design” features.
Everyone in the company contributes to the product. What makes the product team unique is their responsibility to deeply understand the customer’s problem and the value of solving it.
To do that, they need to operate a bit like salespeople. They need to be able to ask a customer: “Would you pay for this?” And if the answer is no, they need to know why. Is it too expensive? Is it missing something essential? Are there better alternatives out there? That’s where real product insight lives.
So in our early days – and still today, when we launch new products – product teams lead the first wave of sales. They don’t start by asking for money. They start by sitting with customers, exploring pain points, and co-developing solutions. Once customers begin using the product, we test pricing. We learn, we improve, and we iterate. Only once that cycle is working do we start to scale.
We actually didn’t hire our first actual salesperson until we had a modest amount of ARR. And even then, we built the team bottom-up: individual reps first, then structure later. Not the traditional “raise big, hire VP Sales” model.
It’s also a great litmus test for product leaders. If they’re happiest inside the building, debating roadmaps but not wanting to talk to customers, that’s a red flag. Great product leaders want to spend at least half their time with users. In person. On calls. Living in their shoes.
And look, not every founder loves spending time with customers either – and that’s okay. But if you’re not that person, you need to hire someone who is.
Dealing with the competition
Jules: Monitoring was, and continues to be, a crowded space. How do you handle competition?
Olivier: We’re in a space that’s always been super competitive. In my first VC pitch, they literally rolled their eyes: “Oh monitoring? It’s a crowded market.” Everyone thought we were crazy to enter it.
But we didn’t – and don’t – obsess over competitors. We only pay attention when customers bring them up. What matters is how your product solves customer problems – not what features are quoted in someone else’s press release. You have to resist the temptation to copy features just to win deals. That leads to commoditization. We stay focused on customer problems and let the competition follow us.
Scaling the team, the culture and yourself
Jules: You’ve gone from two founders to 5,000 people. How do you cope with that level of scale yourself, as the founder?
Olivier: You don’t need to stay in touch with every detail – but you can sample reality from every part of the business. That could mean I read support tickets from customers, look at what’s going on in Salesforce, check what’s coming out of product and sales, and so on. That helps me make sure the high-level narrative matches the ground truth.
And when I ask my team questions about the details, it reminds them that the details matter. But you have to trust them to resolve and execute. You can see the details and understand everything that’s going on and, then, point people to that.
Now it’s very good to look at all the details, but it’s very bad to try and make changes yourself. You can’t go and actually tell the support engineer, “Hey, you have to say that to your customer” nor can you go and tell the Director of Support, “Well, you should do things differently.”
Everything has to go through your management team. You can’t affect any change without going through your management team and the organization. If the people don’t make the changes, then they’re not in the right place, and then you change your organization. But you have to trust your team to make the changes. As one more board member presented it, it’s like you put your nose in, but fingers out.
Jules: That’s some very sound advice. When we think about the team, much of your early hires are still with you. What’s your approach to successfully hiring and retaining talent?
Olivier: Yes, Alex, our first marketing hire is now CMO. Amit, our head of product is now President. One of our engineering leaders started as an intern.
To me, the best people make problems disappear. You give them something hard, and it just gets done. They surprise you with how much better the outcome is than you imagined. Work naturally flows to great people. That’s the clearest sign they’re a keeper. The best feeling isn’t closing a big deal or launching a product. It’s realizing someone you hired is amazing. When you think: wow, this person is fantastic – and it keeps getting better from there.
Jules: On the flipside, what’s a mistake you’ve made during the Datadog journey?
Olivier: We make mistakes all the time. Still do. And the funny thing is, some of them repeat themselves – even when we know better.
The one we keep making is this: we’re too slow to hire, and too slow to fire. Every time we bring in someone great, we say, “why didn’t we do that six months earlier?” And every time we part ways with someone who wasn’t working out, it feels overdue.
This is especially true in the early days, and even more so when it comes to go-to-market roles.
At the beginning of a company, you can often attract world-class engineers. The best engineers want to build from scratch. They’re excited to shape the product, the codebase, and the future.
But the same isn’t true for sales. The best sales leaders usually want to go where they can earn the most, the fastest – and that’s typically not a pre-revenue startup. They’re looking for mid-to-late-stage companies, or ones that already have product-market fit and predictable growth. So your first go-to-market hires probably won’t be perfect. You may need to hire early, learn fast, and upgrade over time as the company grows and becomes more attractive to top talent.
There are exceptions. I’ve seen companies that managed to keep the same sales leadership team all the way from seed to IPO, but I think they got lucky. Most of the time, you need to be prepared to evolve your team as you scale.
One final piece of advice
Jules: Thanks Olivier. So as we wrap up this conversation, and looking back over your journey, what’s your number one piece of advice to early-stage founders?
Olivier: For early-stage, it would be to live with your customer. That’s where the truth is. Everything else – your deck, your narrative, your investor pitch – is just make believe. Customers don’t lie; if they’re paying, or they’re not, that tells you what you need to know.
Thanks Olivier!
