During post-COVID uncertainty, David Obstler spotted early signs of customer optimization and reprioritized Datadog’s investments. By pulling back selectively while sustaining rapid investment in key areas, he preserved profitability, avoided layoffs, and strengthened the company’s ability to reaccelerate growth—building long-term resilience without compromising culture.
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Now Watch the Complete Episode Featuring CFO David Obstler
David Obstler explains how Datadog scaled by pairing product-led growth with disciplined investment. He describes joining in 2018 as observability expanded into logs, application monitoring, and security amid the broader shift to cloud. Datadog now serves 31,400+ customers and recently joined the S&P 500 after reporting over $820 million in quarterly revenue, 28% year-over-year growth, and $200+ million in free cash flow. Obstler emphasizes calibrating spend during uncertainty—“we pulled back a little bit”—to preserve profitability and avoid layoffs while staying close to customers, sustaining mid-to-upper-90s gross retention. Looking ahead, he’s investing in AI capabilities and infrastructure to support global scale.
| CFO’s Strategy Playbook |
|---|
| • Prioritize product-led growth with disciplined investment |
| • Calibrate spend to protect profitability and agility |
| • Use customer signals to guide prioritization |