When David Obstler joined Datadog in 2018, the company’s co-founders had already built momentum with a product that observed modern cloud workloads. What struck Obstler was the alignment with a powerful long-term trend—the shift from legacy, on-premise systems to modern cloud applications. “It was a product that had a lot of product market fit in a really strong growing market,” he tells us.
From that foundation, Datadog scaled rapidly. Today, the platform serves more than 3,100 customers worldwide, including Samsung, Nasdaq, Shell, Autodesk, and Toyota. The company recently entered the S&P 500 after reporting more than $820 million in second-quarter revenue—a 28% year-over-year increase—alongside $200 million in free cash flow, Obstler tells us.
The CFO attributes the growth to Datadog’s unwavering commitment to product-led innovation. The company began in infrastructure monitoring and quickly expanded into logs, application monitoring, and security. “The company invests R&D at very high and consistent levels to continue to maintain and grow the platform,” Obstler tells us.
His own role centers on scaling the infrastructure needed to support expansion. That includes building global go-to-market operations and strengthening his team across financial planning, predictability, and business operations. “We’ve been investing behind this growth opportunity and doing it in a strong, prioritized way,” he tells us.
With new investments in AI, Datadog is preparing for its next chapter. For Obstler, disciplined prioritization and product-driven growth remain at the heart of how finance can fuel scale.
CFOTL: We have more career-related questions, but since you mentioned (Datadog), let’s first talk about the company. Tell us about (Datadog). What was the opportunity that led you to take the leap again back in 2018 (or 2019) when you joined?
Obstler: Datadog’s co-founders, Olivier Pomel and Alexis Le-Quoc, did a great job finding product-market fit and investing in a product that observed modern cloud workloads. Over time, that expanded into observability and security—really, seeing how cloud workloads function. It aligned with a powerful long-term trend: re-platforming from legacy, on-premise applications to modern cloud applications. The product had strong product-market fit in a growing market. Today, we have over 3,100 customers of all sizes globally—Samsung, Nasdaq, Shell, Autodesk, Toyota. We recently joined the S&P 500, reflecting years of growth and strong performance. In Q2 (ended June), revenue was over $820 million, 28% year-over-year, with over $200 million of free cash flow. For the last five to ten years, the company has scaled against strong demand… with the right product in the right market.
CFOTL: From the CFO seat, what’s fueling this growth, and how are you balancing investment across product lines?
Obstler: First, there’s a long-term secular shift of applications to the cloud, which drives demand. We’re a product-led growth company, so we invest in R&D at high, consistent levels to maintain and expand the platform—starting in infrastructure monitoring and moving into logs, application monitoring, security, and more. AI is another investment area that we believe will further propel growth. My job is to build the infrastructure to support it: scale go-to-market globally and grow my team across financial planning, predictability, business operations, facilities, etc. We invest behind the opportunity in a prioritized, disciplined way to take full advantage of this market.