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Uber engineers built an AI version of their boss

Read the full articleUber engineers built an AI version of their boss on TechCrunch

What Happened

Uber CEO Dara Khosrowshahi said the company’s employees have gone all in on AI, going so far as to build a chatbot of him that they use to practice their pitches.

Our Take

Honestly, building an AI version of your CEO for pitch practice is either genius or the most dystopian thing I've heard. But it works—rehearsal against a knowledgeable opponent beats talking to yourself.

The wild part? Nobody's freaking out about it. People are just using it to get better. That's a tonal shift worth noticing: AI-as-tool is so normalized inside orgs now that it doesn't even register as weird.

What To Do

Try this internally: record pitches, feed them to Claude with 'critique like a skeptical investor'—cheaper than hiring a coach.

Builder's Brief

Who

internal tooling and developer experience teams

What changes

Normalizes persona-cloning of leadership for internal use, raising new questions about voice/likeness consent policies

When

months

Watch for

A formal HR or legal policy at a major employer explicitly governing AI persona use of executives

What Skeptics Say

A CEO chatbot trained on public statements teaches pitch-rehearsal against a sanitized persona, optimizing for approval signaling rather than substantive business reasoning—a productivity theater exercise.

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