The a16z Show

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The CISO Playbook for AI Agents | Datadog

Explore episode Aug 11, 2026

Where this was said

The CISO Talent Problem and Waiting for Vendors

At 14:00 · chapter starts 12:00

Escobar recounts a roundtable on agentic security he led the previous week where the dominant emotion among participants was helplessness — a waiting game for commercial products to make the problem go away. He finds this troubling, not because buying security products is wrong, but because the space is moving too fast for passive observation. De la Garza picks up the thread, tracing the talent gap back to the CISO role's origins: the title barely existed a generation ago, and when security teams grew large enough to need managers, the profession hired managers — not technologists. That history means a lot of CISO programs are structured around procurement rather than building. For companies where software isn't the competitive advantage, that's defensible. For companies like Datadog, it isn't.

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