
CFO THOUGHT LEADER 1130: Building Resilient Finance in Uncertain Times | David Obstler, CFO, Datadog
Sep 28, 2025
David Obstler, CFO of Datadog, leads a company that has revolutionized cloud observability and recently entered the S&P 500. He discusses scaling from $300M ARR to a multi-billion run rate, attributing success to disciplined, product-led growth and R&D investments. Obstler emphasizes the importance of adapting finance strategies during economic shifts while maintaining profitability. He also shares insights on integrating AI into operations, the evolution of finance teams, and advice for new CFOs, highlighting the value of fostering trust and collaboration with founder-CEOs.
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Platform Aligned To A Secular Cloud Shift
- Datadog rode a clear secular trend: replatforming from legacy to cloud-native applications.
- Product-market fit plus sustained R&D investment enabled expansion across observability and security.
Invest And Validate Through Customer Signals
- Invest consistently in R&D to expand a platform into adjacent product areas.
- Validate new products by listening to customers and experimenting while integrating tightly into the core platform.
Calibrated Investment Protects Retention
- Datadog balanced growth with disciplined profitability and calibrated investments during uncertainty.
- That approach preserved high gross retention and avoided workforce reductions.






