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

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Olivier Pomel is the Founder & CEO @ Datadog, the company building the next generation of tools for DevOps teams. Prior to their incredibly successful IPO in 2019, Olivier raised over $147M for the company from Index, ICONIQ, Meritech, IA Ventures, Amplify and OpenView, to name a few. Prior to founding Datadog and changing the world of devops, Olivier was a VP with Wireless Generation for 8 years leading an engineering team of close to 100 of the best developers in NYC.

In Today’s Episode with Olivier Pomel You Will Learn:

1.) How Olivier made his way into the world of startups and what was the a-ha founding moment for his creating of Datadog, changing the world of devops?

2.) Why does Olivier believe that "short term failure is a source of long term success?" Why did both seed and Series A investors not get Datadog? What would Olivier have done differently if fundraising again? What do investors misunderstand today when investing in big markets looking for the "entry wedge"?

3.) What has been Olivier's biggest learnings on how to run Datadog during a pandemic? What attributes does Olivier look for when hiring senior leaders? Why does Olivier believe the CEO has to be the "equaliser in chief"? What does that mean in practice? How can leaders creat eenvironments of safety where their team can approach them with anything?

4.) What have been the biggest challenges in moving from a single product to a multi-product company? How does one know when is the right time to add additional products? What is Olivier's decision-making process to determine which products to build next?

5.) How does Olivier assess his relationship to money today? How has it changed over time? In what ways has becoming a father impacted Olivier's operating mindset? What 3 traits would Olivier most like his children to adopt?

Item’s Mentioned In Today’s Episode with Olivier Pomel

Olivier’s Favourite Book: Kurt Vonnegut

As always you can follow Harry and The Twenty Minute VC on Twitter here!