Olivier Pomel (Datadog): Reimagining observability for the AI-powered enterprise

Datadog co-founder and CEO Olivier Pomel joins Pigment co-CEO Eléonore Crespo to discuss how AI is reshaping software operations – including why teams now spend more time running applications than building them, what it takes to trust AI-driven automation in mission-critical systems, and how Datadog maintains product simplicity while serving both startups and Fortune 500 companies. In this interview, Olivier shares his take on why observability has become essential as AI accelerates system complexity, the discipline behind fast feedback loops, and why false positives will kill AI adoption faster than anything else. Key topics: Why observability matters more than ever How AI shifts engineering work from primarily building to primarily operating software What decisions should remain human-centered versus fully automated Calibrating trust in AI systems and the 90%+ accuracy threshold How Datadog organizes for AI adoption with both top-down and bottom-up approaches Why second-generation coding agents unlocked explosive developer adoption Building outside Silicon Valley and staying grounded in customer problems The biggest opportunity and underestimated risks as enterprises adopt AI Guest: Olivier Pomel, Co-Founder and CEO of Datadog Host: Eléonore Crespo, Co-CEO of Pigment Series: Perspectives by Pigment Chapters: What is observability, and why does it matter for AI? (00:00) The ultimate vision: systems that fix themselves (03:25) What should remain human-centered versus fully automated? (06:24) Calibrating the right level of trust in AI and building the right guardrails (11:35) How to differentiate AI hype from real business value (16:09) Top-down versus bottom-up AI adoption and building a culture of experimentation (18:58) Why the second generation of coding agents changed everything (24:47) How leadership and product building have evolved (26:46) Building outside Silicon Valley’s gravitational pull (30:05) Maintaining simplicity across a diverse customer base (34:35) The biggest opportunities and risks ahead (38:27) Datadog’s incremental, transparent approach to product-building (44:18) How to stay informed on AI (45:40) Read the key takeaways here: https://www.pigment.com/perspectives-...