Most companies wait for their tech team to lead AI adoption. At Howard Hughes, the push started from the CFO's office.
Carlos Olea spent decades mentally cataloging process inefficiencies — as an auditor, he'd spot problems he had no authority to fix; as a finance leader, he'd hit budget or technology walls. When AI broke through both barriers, he pulled out his backlog and started building. His first project? A tool that parsed vendor bids to surface the best value — not just the cheapest price. That small win opened the door to automating lease abstraction, a notoriously manual process in real estate, with higher accuracy than humans.
Carlos talks about the risks of being a "very different CFO," why imagination — not tools or budget — is now the real bottleneck, and how he assembled a tiger team that moves at startup speed inside a public company. His playbook for winning over skeptics: fix the tasks everyone hates first.
- Why a CFO — not a CTO — became Howard Hughes' AI champion
- The decades-long efficiency backlog that finally found its tools
- How to pitch AI to your board when you don't have a tech background
- Why chasing every new model is the fastest way to accomplish nothing
- Building a tiger team that blends enterprise rigor with startup speed
Carlos Olea — Chief Financial Officer, Howard Hughes Holdings. A CPA-turned-AI-builder who led the company's first AI investments and now runs its innovation push from the finance function.
Howard Hughes Holdings: https://www.howardhughes.com/
Carlos Olea on LinkedIn: https://www.linkedin.com/in/carlosolea/
