Caterpillar has been selling autonomous machines for years — haul trucks, drills, dozers — mostly to mining operations where labor is scarce and conditions are dangerous. Now the company is betting it can take that hard-won expertise into messier environments: construction sites, quarries, and the daily workflows of its 118,000 employees.

That means tools like the Cat AI Assistant, a voice-controlled system that lets technicians standing next to a broken machine pull up repair procedures, troubleshoot issues, and identify parts before they start work. CTO Jaime Mineart says it’s already in the hands of customers and operators. The assistant works because Caterpillar sits on an enormous data trove: roughly 1.6 million connected assets worldwide generating more than 16 petabytes of structured data. That’s the kind of proprietary fuel most AI startups can only dream about.

The company is also deploying AI for digital twins in manufacturing, site scanning, and the unglamorous work of modernizing legacy code. “We use AI agents to modernize legacy code, generate and test new software, and identify defects earlier,” Mineart said at the Ai4 conference in Las Vegas. It’s the same enterprise AI story playing out across every Fortune 500 company — except Caterpillar is doing it with physical machines that can kill people if the software gets it wrong.

That’s where the $100 million comes in. Mineart said the company will spend that amount over five years training employees in AI, autonomy, and robotics. The challenge isn’t just teaching people to use new tools; it’s rethinking how jobs change when one operator oversees multiple machines from a remote command center instead of sitting in a single dozer. “The hard part about autonomy and about physical AI is incorporating that technology into the customer jobsite and into the workflows,” she said. The AI boom is already showing up on the balance sheet — quarterly revenue hit a record $20.5 billion in Q2, with power-generation sales up 72% on data center demand. CEO Joe Creed put it bluntly: “No one is slowing down” on cloud and generative AI infrastructure. Caterpillar isn’t just selling the picks and shovels of the AI gold rush. It’s trying to become one of the miners too.