Uber's Engineers Cloned Their CEO's Brain for Pitch Practice

What happens when your engineers get so tired of bombing CEO presentations that they literally build a digital twin of your boss?

Uber just gave us the answer. During a February 24th appearance on "The Diary of a CEO" podcast, CEO Dara Khosrowshahi dropped a bombshell: his engineers built "Dara AI" - a chatbot that simulates his responses so teams can practice their pitches before the real deal.

This isn't some weekend hackathon project. It's part of Uber's massive AI transformation where 90% of software engineers use AI tools daily, with 30% as "power users" completely rethinking technical architecture. Khosrowshahi called the productivity impact "unlike anything I've witnessed before in my career."

The Technical Cocktail Behind Digital Dara

Building an executive simulator isn't trivial. Dara AI likely combines:

• Natural language processing for complex business queries
• Pattern recognition from Khosrowshahi's historical decisions
• Contextual awareness of Uber's priorities
• Feedback integration from actual meetings

The engineering team probably fine-tuned large language models using public statements, emails, and meeting recordings. Smart developers could replicate this approach for their own organizations - imagine having a CTO bot to stress-test your architecture proposals.

From $3B Losses to AI-Powered Everything

This move makes perfect sense given Uber's transformation. Khosrowshahi took over in 2017 when Uber was bleeding $3 billion annually. Now they're generating over $9 billion in free cash flow.

The company isn't stopping at CEO chatbots either. Recent launches include:

1. Uber Autonomous Solutions for robotaxis

2. AI Solutions initiative (October 2025) letting contractors train AI models via phones

3. Predictions of majority robot-operated trips in 15-20 years

Uber positions itself as a technology company where engineers are the core "builders" - and apparently, they're building everything, including their boss.

When Meetings Get Too Easy

Here's what's fascinating: teams now show up to CEO meetings with incredibly polished presentations because they've already been grilled by Digital Dara. No more stumbling through questions. No more "um, let me get back to you on that."

But is this actually good?

The upside is obvious - streamlined processes, reduced meeting friction, better preparation. The downside? Over-reliance on simulations might create an echo chamber where teams only prepare for predictable responses.

Hot Take: This Is Brilliant and Terrifying

Let's be honest - Dara AI is genius-level problem-solving. How many times have you walked into a stakeholder meeting unprepared, only to get demolished by questions you should have anticipated?

But here's the uncomfortable truth: if you can simulate a CEO's decision-making patterns accurately enough for pitch practice, you're uncomfortably close to automating that CEO.

Khosrowshahi himself predicts AI will replace 70-80% of human work in the next decade. His advice? Simply "work hard." That's... not particularly reassuring coming from someone whose digital twin already exists.

The real question isn't whether this technology works - clearly it does. It's whether we're building tools that enhance human capability or quietly replacing human judgment entirely.

What happens when Dara AI starts giving better feedback than actual Dara?

For now, Uber's engineers seem thrilled with their productivity gains. But in a world where your boss can be simulated, trained, and potentially replicated, the line between augmentation and replacement gets blurrier every day.

Maybe the most human thing about this story is that engineers, faced with a challenging boss, didn't complain - they just built a better version to practice with first.