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The Observatory

Building & Agents · 1 min read

Define the Role Before the Role Defines You

Greg Brockman's essay "Figuring Out the CTO Role at Stripe" argues that technical leadership is not a fixed job description you inherit but a function you must actively shape — and the same logic applies, with new urgency, to founders building companies where agents are doing the actual work.

Featuring · studied & reframed for AI-native builders“Figuring Out the CTO Role at Stripe” — Greg Brockman ↗

You Cannot Be the Best Agent in the System

Brockman realized early that trying to remain the best individual technical contributor was a trap. The more the system grew, the more that posture became a bottleneck. Founders shipping with agents face the same temptation in a sharper form: the urge to stay close to every prompt, every tool call, every output. That instinct is understandable but self-defeating. Reliable agentic work comes from clear task definitions, well-scoped tools, and evaluation harnesses — not from a founder heroically reviewing each run. Your leverage is in designing the system, not operating inside it.

Standards Are Infrastructure, Not Overhead

Brockman's answer to the bottleneck problem was to invest in culture, standards, and tooling so that good decisions propagated without him in the room. For an AI-native company, the equivalent is the evaluation harness: build the evals before you build the agent, let red cases drive the design, and treat measurement as load-bearing infrastructure. A workflow your team cannot measure is a workflow your team cannot trust in production, which means it cannot scale.

Judgment Is the Non-Delegable Part

What Brockman kept for himself was judgment on the hardest calls — architecture direction, trust decisions, the moments where ambiguity was real. That residue maps cleanly onto what autonomous systems still require humans to hold: setting goals, defining boundaries, and owning accountability when things go wrong. The CTO role Brockman defined was, at its core, a human-judgment role dressed in technical clothing. So is the founder role at a company where agents handle execution.

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