The AI-First CEO: Episode 2
Crow Holdings has 75 years of real estate history. Todd Dooling is making sure the next chapter is written by AI. In Episode 2, VirtuousAI CEO Chris Happ and legendary category creator Christopher Lochhead sit down with Todd Dooling, CIO of Crow Holdings, for one of the most honest conversations about AI leadership you'll hear anywhere. No theory. No hype. Just what it actually takes to rewire a sophisticated, multi-entity real estate organization around AI — from the culture up. The line that changes how you think about AI:"AI is not a bolt-on, an assistant, a co-pilot. No, no, no. AI is the co-founder of my company." — Christopher Lochhead Todd doesn't just agree; he's living it. From automating invoicing to rethinking how an entire department shows up for the business, this episode traces the real inflection points that separate AI talk from AI transformation. What you'll hear: How Todd rebranded IT as "Business Technology" — and why the shift goes far deeper than semantics Why Crow Holdings gave employees "lots of rope" and what that has to do with AI adoption working at scale The moment Todd realized AI wasn't a tool to add — it was a foundation to build on How to move from incremental AI wins to compounding competitive advantage The cultural and people challenges no vendor will warn you about If you're a real estate leader or CEO serious about putting AI at the core of how your business operates — not as a bolt-on, but as the engine — this conversation is required listening. About the Guest Todd Dooling is the Chief Information Officer of Crow Holdings. Since 2018, he has led enterprise technology strategy, cybersecurity, cloud modernization, and AI governance across a national real estate platform — deploying GPT Enterprise, Microsoft Copilot, and VirtuousAI. Two decades of large-scale transformation. Rare strategic clarity. The credibility to back it up. Your Hosts Chris Happ is the CEO of VirtuousAI and a serial entrepreneur focused on helping mid-market companies close the Execution Gap — the costly distance between where they want to go and their ability to get there.Christopher Lochhead is a legendary category designer, bestselling author of Play Bigger and Category Pirates, and one of Silicon Valley's most provocative strategic minds. About VirtuousAI VirtuousAI builds BAIO, the Corporate Brain for mid-market companies — a continuous operating environment where finance, sales, marketing, and operations draw from the same connected intelligence in real time. The result is radical alignment, with strategy and execution architecturally connected, not periodically synced. Brands already running on BAIO include Crow Holdings, Mugsy, Ziosk, Conewago, Footwear Unlimited, Puroast, FRYE, and Smoker Craft. They didn't add an AI tool. They gave their entire organization a shared brain.