"Putting a dollar amount on features focuses customers’ minds like nothing else."

The First $100,000,000 ARR at Datadog: How Founder CEO Olivier Pomel Built a Customer‑Centric Observability Giant

Jason M. Lemkin 🦄 – Nov 17 2025

Ahead of SaaStr AI London (Dec 1‑2) we’re looking back at one of our favorite sessions from the European events. Olivier Pomel, founder‑CEO of Datadog, joined us as they crossed $100 million ARR in a candid conversation that would be harder to have today post‑IPO.

The First $100,000,000 ARR at Datadog: How Olivier Pomel Built a Customer‑Centric Monitoring Giant

From zero lines of code to 700 employees and doubling revenue annually, Datadog CEO Olivier Pomel shares the counter‑intuitive strategies that built one of the most customer‑obsessed companies in B2B SaaS.

Olivier’s Top 5 Toughest Learnings

1. You can’t be customer‑focused if you’re sales‑driven OR engineering‑driven – Most companies fall into one trap or the other. Sales teams optimize for closing the next deal (short‑term), while engineering teams build for the long‑term without bridging back to customers. Customer‑centricity requires daily vigilance against both.

2. Closed alphas with “perfect customers” give terrible signal – Hand‑picking the best companies and best people for early access actually makes it harder to learn. Customers need to self‑select when the timing is right for them. Open betas revealed infinitely more than curated alphas ever did.

3. Month‑to‑month contracts are better than annual deals for learning – Every instinct (and investor) tells you to sell annual contracts. But monthly contracts force bad news to surface immediately instead of a year later. A year of going in the wrong direction is devastating for a young company.

4. There’s no MVP for enterprise infrastructure – The conventional wisdom about shipping minimal products doesn’t apply when selling to enterprises who need comprehensive solutions. You need depth across many features before you’re minimally useful. It’s a continuum, not a single viable moment.

5. Pricing conversations reveal product truth better than any metric – “Putting a dollar amount on features focuses customers’ minds like nothing else.” When customers say “I won’t pay for that,” you get brutally honest feedback about value. This friction is healthy and teaches you where to go next.

When Olivier Pomel and his co‑founder started Datadog in 2010, they didn’t write a single line of code for the first six months. For two engineers itching to build, this took “some restraint,” as Olivier puts it. That decision to obsessively listen before building became the foundation of a company that would redefine infrastructure monitoring and grow to 700 + employees while doubling in size every single year.

At SaaStr Europa, Olivier pulled back the curtain on how Datadog became one of the most customer‑centric companies in enterprise software—and why being truly customer‑focused requires constantly fighting against your natural instincts.

The Problem: When Great Teams Hate Each Other

The genesis of Datadog came from a painful problem Olivier and his co‑founder experienced firsthand. Despite working together across four different companies, knowing each other extremely well, and building their teams from scratch with a “strict no‑asshole policy,” they ended up in a familiar nightmare scenario two years in.

“We ended up with developers that hated operations, operations that hated developers, finger‑pointing—all of the things that you can imagine,” Olivier explained.

The question became simple: Why don’t we give all of those teams the same viewpoint? How do we get them aligned and understanding their infrastructure the same way?

This became Datadog’s founding mission—bringing DevOps together and bridging the gap between development and operations teams. What they didn’t fully realize at the time was that this wasn’t just a nice‑to‑have feature. It was actually one of the key reasons why companies would migrate from legacy IT to the cloud.

“We ended up right in the center of it. Today the company is about 700 people. We’ve been doubling the size of the company every single year. It turns out everybody is moving to the cloud and everybody needs to understand what’s happening to their systems and applications.”

The Counterintuitive Truth About Customer‑Centricity

Here’s the part most founders get wrong: you can’t be customer‑focused if you let your company become sales‑driven OR engineering‑driven.

“Everybody wants to be customer‑focused,” Olivier noted. “But most companies end up being either sales‑driven or engineering‑driven. If you want to be customer‑focused, you can’t be either of those.”

The Sales‑Driven Trap: Sales teams are phenomenal at figuring out what’s going to get a deal done. But very often, getting the next deal done is not what you want to do for the long run for your customers. Short‑term thinking dominates.

The Engineering‑Driven Trap: Let your engineering teams run on their own, and you’ll end up with organizations where people focus way too much on their solutions and way too much on the long term. You’ll struggle to bridge that gap back to the customer.

The solution? “It’s a struggle every day to make sure that we go back to the customer and start from there.”

This wasn’t a conscious choice at first—it was forced upon them. Starting in New York (not the Bay Area), without Google or Facebook pedigrees, without millions in funding, and without a suite of VCs telling them they were geniuses, Datadog had no choice but to obsessively focus on the problem.

“We basically had to focus on the problem. We spent the first couple of years listening to customers and trying to understand what the problem was.”

The First Two Years: Why They Didn’t Write Code for 6 Months

When you’re engineers and you start a company, every instinct tells you to build. Olivier and his co‑founder resisted this for six months—and discovered something remarkable.

When you don’t have anything to sell, everybody is super happy to talk to you.

“You’ll get hours and hours of really fantastic people at fantastic companies and they’ll spend all that time explaining to you what their problems are, what’s working, what’s not working for them. They’ll be extremely candid.”

This changes the moment you have something to sell. “Then you’re tainted. You have too much of a vested interest and you’re trying to push something, so people won’t open up so easily.”

After six months of research, they spent another six months building their first alpha. When they deployed it to a small number of customers, they noticed the product was “way too open‑ended, way too general.”

But here’s where they made a critical discovery that contradicts conventional wisdom about customer selection.

The Open Beta Revelation: Let Customers Self‑Select

Datadog initially ran a closed alpha, hand‑picking the best companies and the best people at those companies. “It was actually really, really hard to get a lot of signal from these customers,” Olivier admitted.

Then they opened it up to a wide beta—and everything changed.

“It’s a lot easier for users to self‑select and start using your product than for you to understand for whom you’re going to be the right thing at the right time.”

You can’t predict when customers will have free bandwidth, when all the stars will align for deployment, or when your solution will be exactly what they need. Let them tell you by trying it.

This open approach became core to Datadog’s growth strategy and fed directly into their customer‑centric philosophy.

Why Datadog Doesn’t Believe in MVPs

Ask most SaaS founders about MVPs and you’ll get textbook answers about shipping fast and iterating. Olivier has a different take.

“I don’t think there’s an MVP for what we do. I think it’s a myth.”

Datadog sells to enterprises that need to monitor everything happening across entire infrastructures and applications. There’s a very large number of features customers rely on, and none of these features in themselves are revolutionary.

“You need to have them, otherwise you cannot be minimally useful. It’s more of a continuum—you keep adding those features, and at a certain point you have enough of them that customers can start buying.”

The hard part? Figuring out which features matter most. “That’s why you have to go back to the customer and make sure you have enough of them so you can actually extract some signal from those conversations.”

For enterprise B2B infrastructure companies, the MVP concept often doesn’t apply. You need depth before customers will even consider you.

Scaling Customer‑Centricity: The 10‑100 Person Phase

When Datadog hit the market, they were about 10‑15 people. The phase of reaching initial scale ran from there to just under 100 people. This is where most companies start to lose their customer focus—but it’s also where you can build the most powerful feedback mechanisms.

Strategy #1: Only Sell Month‑to‑Month Contracts

“We didn’t sell yearly deals for a very long time. We only sold month‑to‑month, meaning customers had the opportunity to churn all the time.”

This was structural, not accidental. If something is wrong with the product, if you don’t solve the right problem, if it’s not valuable enough—you know right away. Customers churn and you can have a conversation with them.

“If you start selling term deals, you’re going to have the bad news about a year later. By then you …”

(The interview continues with further strategies and reflections on scaling, but the core lessons above capture the essential takeaways from Olivier Pomel’s journey to $100 M ARR.)