AIWA "The One Thing" #27: Uber's COO Named the AI Gap. Its CTO Closed it in 60 Days. Forward Deployed FTW.

I'm not a hedge fund manager. But Uber is a Buy.

Read Praveen Neppalli Naga's digital receipts and you'll see why.

*Link to Praveen Neppalli's tweet

Uber's CTO took its most AI-proficient engineers and paired each one with a domain expert from a business function. Finance. Legal. Operations. Marketing. Support.

Two weeks per pod. Ride shotgun. Shadow the work.

Build the agent next to the person doing the job. Ship.

Sixteen pods. Sixty days. The receipts:

Capital allocation across 150 cities. 15 hours to 30 minutes.

Financial pacing reports. 2 days to 10 minutes.

Marketing web quality assurance. 2 weeks to 50 minutes.

Support workflow creation. 9,000 manual workflows to self-service automation.

The results are impressive. The timing is the story.

Remember the headline in May?

*"Uber burned through its entire 2026 AI budget in four months. Now its COO is questioning whether it's worth it." by Fortune 05.26.26

Most people never read the piece or watched the podcast. The headline did the work. It moved by word of mouth. Twitter threads. Podcast asides. Group chats.

And it hardened into one line tied to “tokenmaxxing”: Uber is pulling back on AI.

It never happened.

Watch Andrew Macdonald on Rapid Response starting around the 27th minute. He didn't question their AI commitment. He questioned the math.

Someone pays for the tokens. And nobody had yet drawn a clean line from token spend to net new features. His point was conditional.

He wasn’t pulling back, he was leaning in, looking very closely for the ROI line.

Ninety seconds later he called autonomy existential for Uber. Existential. That is not a leader reconsidering AI.

A measurement question got spun as a retreat. Then Uber answered its own question.

Three things land it for me.

One. Rewire.

In TOT #16 I laid out Automate, Augment, Rewire.

*AIWA TOT #16: The Unit of Production Just Changed. Automate. Augment. Rewire. (From my RDSW Talk)

Uber is deep in Rewire.

"The biggest wins rarely come from automating one task. They come from rethinking an entire workflow." Redesign the workflow around AI and you eliminate handoffs, remove approvals, replace legacy tooling, cut vendor spend. The workflow is the unit of automation. Not the task.

Two. Forward Deployed.

"The best AI opportunities are rarely visible from the outside. You discover them by sitting next to the people doing the work, understanding every friction point, and building with them, not for them." That is the senior operator FDE. The human layer that closes the gap.

Three. The receipts answer the skeptic.

Macdonald wanted a line from spend to value. Pods draw it in outcomes, not token counts. That isn’t “tokenmaxxing.” That's the right token for the right job.

The headline sold a retreat. The digital receipts show a company that found the line every CFO is looking for.

Humans + Machines. Never Humans vs. Machines.