Apr 5, 2021 · 36m · 20vc
20VC: Datadog CEO Olivier Pomel on The Scaling Journey to a $26Bn Market Cap, The Challenges in Moving From Single To Multi-Product Company & How To Scale Efficiently into $M+ Enterprise Deals
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The Twenty VC podcast, host Harry Stebbings interviews Datadog co-founder and CEO Olivier Pomel about Datadog's journey from an early-stage startup to a $26 billion public company. Pomel shares insights on overcoming early fundraising rejections, expanding from a single monitoring tool into a multi-product enterprise platform, and maintaining empathetic leadership through rapid scaling and macro crises.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 33% of the talking time here. How this is scored →
Harry as informed peer 2.6 Guest teaching 3.5 Guest disagreement 1.3 Harry pushing back 1.3
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 26:07 Rejection of Business Books and Startup Advice
Olivier directly criticizes startup self-help literature and cocktail party advice as useless, insisting that real business truths are found in granular operational details rather than generic books.
Hardest push from Harry ▶ 7:21 Host Challenge on Pre-Revenue ValuationsHarry interjects with a real-world example of a pre-revenue company valued at $300M to validate and push on Olivier's critique of inflated market expectations.
Biggest teaching moment ▶ 5:50 Reframing the Product Wedge MythOlivier corrects common venture capital assumptions by explaining why infrastructure management tools cannot rely on a narrow product wedge to succeed.
Harry holds his own ▶ 22:14 Citing SaaStr Rules on Founder BurnoutHarry displays venture expertise by invoking Jason Lemkin's investment criteria regarding founder fatigue, steering the discussion on M&A and founder persistence.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Founding Vision and Overcoming Early Failure | 2 | 3 | 1 | 1 | Harry introduces the episode and asks about Datadog's early days and founding realization. Olivier explains how early fundraising rejections forced the company to focus on customer-centricity and capital efficiency from first principles. | |
| Raising Series A and Misconceptions Around Product Wedges | 4 | 5 | 2 | 2 | Harry quotes investor Sunil at Amplify regarding Series A hurdles. Olivier reframes standard venture capital wisdom by explaining why infrastructure management cannot rely on a single sharp product wedge, prompting Harry to share his own VC concerns about pre-revenue valuations. | |
| Product Simplicity and Scaling Go-To-Market to Enterprise | 3 | 4 | 1 | 1 | Harry asks about keeping products simple and scaling go-to-market motions into multi-million dollar enterprise deals. Olivier educates that product simplicity stems from serving a wide customer spectrum rather than just hiring UX designers. | |
| Operational Adaptation and Human-Centric Leadership During COVID-19 | 2 | 2 | 0 | 1 | Harry asks about leading through the pandemic and executive hiring criteria, relaying a question from Dev at MongoDB. Olivier shares how Datadog instituted employee community grant programs and prioritized human adaptability. | |
| Executive Demeanor, Equanimity, and Psychological Safety | 2 | 3 | 1 | 1 | Harry asks about executive demeanor, psychological safety, and expanding from single to multi-product offerings. Olivier highlights the concept of executive equanimity and explains how infrastructure monitoring provided the foundational surface area for product expansion. | |
| M&A Philosophy, Capital Efficiency, and Scaling Teams | 4 | 4 | 2 | 2 | Harry brings up Jason Lemkin's view on founder burnout to prompt Olivier on M&A philosophy and headcount scaling. Olivier critiques magical thinking around hiring, explaining that recruiting requires clear capacity and ramp modeling just like sales. | |
| Business Philosophy, IPO Realities, and Wealth Creation | 3 | 5 | 3 | 2 | Harry asks about Olivier's aversion to business books, public market leadership, and the impact of wealth. Olivier dismisses business books and cocktail party advice in favor of granular company data, while reframing the IPO as a starting line rather than a finish line. | |
| Quickfire Round: Insights, Leadership Values, and Future Outlook | 1 | 2 | 0 | 0 | The interview concludes with a lighthearted quickfire round covering favorite authors, handling high-stress moments, and personal mentorship values in an entirely collaborative tone. |
Statements from this episode (22)
Pomel: Datadog struggled to raise capital when founded in 2010
“It was actually very hard to raise money for Datadog initially, back in 2010 when we started it”
Pomel: Co-founders balance each other during emotional low points
“I think that's one of the reasons why it's good to have a co-founder, because your laws are not completely aligned, so there's always someone to pull the other up in those times.”
Pomel: Infrastructure management software cannot rely on a narrow product wedge
“Turns out for some classes of problems, such as infrastructure management, which is what we do, the wedge doesn't work. Like there's a large amount of stuff you need to do from day one if you want your product to be useful.”
Stebbings: Pre-revenue startup with five design partners raised at $300M valuation
“I just met with a founder that's just It's getting around done at a three hundred million post, they're pre-revenue, and they've got five design partners.”
Pomel: Product simplicity is driven by customer base, not design
“To a large extent, the simplicity of the products is driven by the user base you have for those products.”
Pomel: In 2013, only startups operated at scale in cloud
“Eight years ago, the only companies that were at scale in the cloud were new companies and smaller companies. The larger enterprises were not there yet.”
Pomel: Enterprise product feedback must be counterbalanced by SMB input
“If you're going to spend more and more time with enterprise customers and give them more and more of a voice in your product, you need to make sure you counterbalance that with voices from the SMB and the low end as well.”
Datadog employees donated $1 million to communities from company pandemic grants
“We actually gave grants to our employees to help them solve their own problems. We also decided to donate some of these grants because some people were feeling bad. They're feeling okay themselves, but they're really feeling really depressed and bad about thei…”
Datadog rejects executive playbooks in favor of leaders willing to learn
“The most important for us is the desire and the ability to learn. We don't think we've got So to speak, or should figure it out in general, we think we still have to learn pretty much everything, and that goes back to the early days of humility and trying to m…”
Pomel: A CEO's role is being 'equalizer in chief' during highs and lows
“As a CEO in general, you have to be the equalizer in chief, you know, so when things look great, you have to temper people's enthusiasm a little bit and say, hey, This looks great, but, you know, all these other things are still broken, we need to fix them. Wh…”
Pomel: Leaders must constantly engage in details or employees stop communicating
“You actually have to show real interest. And you have to engage with the details, because otherwise people stop telling you things, like if they realize you don't even know what they're talking about, or you're just waiting for them to leave your office, you k…”
Infrastructure monitoring is an ideal landing wedge due to wall-to-wall deployment
“That first product, that infrastructure monitoring, is the perfect place to land, you know, because it gives you a very large surface of contact with your customer's environment. An infrastructure monitoring product needs to see all the infrastructure, so it's…”
Pomel: Datadog decided to IPO only after APM and logs succeeded
“When we started seeing APM and logs really take off, That's when we decided to take the company public, because that's when we saw the proof that the company's ultimate vision was right, and we gained confidence that we could see or deliver a lot of growth for…”
Pomel: Customer DIY hacks signal valid opportunities for new products
“Before we started with our APM product, we saw customers build poor man's APM on Datadog. Before we started launching our security products, we saw customers also solve their own security use cases with Datadog. So seeing customers solve the problems with us t…”
Pomel: Multi-product scaling requires a culture willing to fail on new products
“I think the thing that's the hardest is that when you're successful with one product, you're used to being successful and you're used to being right, and to having a good product that's fully fledged and everything else. When you start new products, you're goi…”
Pomel: Quadrupling team size in one year paralyzes company operations
“If you try to do things like quadrupling the size of the team in one year, chances are maybe it's going to be great a few years from now, but for the next year, two years, you're going to be completely out of commission. Like, your team will not do anything ex…”
Pomel: Datadog never more than doubled engineering headcount in a year
“We've been a little bit more measured early on, like we've never done more than double the size of the engineering team in one year, for example.”
Pomel: Tech companies must scale recruiting capacity like sales teams
“When you think of things like recruiting, for example, you really should think about it like you do of a sales team. Like, it scales the same way. Like, a recruiter is going to have a given productivity, and if you want to go to a team in a certain way, you ne…”
Pomel: Datadog waited too long by hiring Head of People past 50 headcount
“We were past 50 people when we had our first head of people, I think. We should have hired that person earlier. I would say earlier than that is my answer.”
Pomel: Startup ground truth comes from internal operational data, not general advice
“The truth is usually in the details of your business. So it's not on the five liners you get from somebody at the cocktail party. Instead, it's looking at dozens of hundreds of customer emails, what's happening in your CRM, what's happening in your support cas…”
Pomel: Long-term investors often flip IPO shares immediately on 40% gains
“Many of them actually, even the long, the good long-term investors, like, they buy into your IPO, and they flip it right away because they've made, you know, 40% in one day, and that's good enough for them, and then they'll come back later.”
Pomel: NYC startups must pitch constantly due to intense competition
“Well, in New York, you're competing with so many other things. Like, you're competing for talent, you're competing for space, at least you're used to, you know, for office space. You're competing for attention with a million other things. That's also what make…”