September 1, 2026
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:
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:
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.
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.
Christopher Lochhead is a thirteen-time #1 bestselling co-author, renowned category designer, entrepreneur, and business podcast host. Widely known as the “godfather” of Category Design, he has helped shape how companies create and define new markets.
A former three-time Silicon Valley public-company CMO, Lochhead has advised more than 50 venture-backed startups and is a venture capital limited partner. He is the co-author of Play Bigger, Niche Down, Snow Leopard, and Category Design Toolkit, among other works exploring marketing, innovation, and category creation.
Today, Lochhead is focused on helping entrepreneurs, marketers, and creators design a different future through Category Pirates, while continuing to challenge conventional thinking through his #1-charting business and marketing podcasts.
He joins Chris Happ on The AI-First CEO Podcast to explore what it takes for leaders and companies to think differently—and build for an AI-first future.
Chris Happ is the CEO of VirtuousAI, where he’s pioneering a new era of execution for mid-market businesses with BAIO—the world’s first Business Automation, Intelligence & Outcomes platform. A serial entrepreneur and seasoned technology leader, Chris has spent his career transforming how companies operate, scale, and win with data.
Driven by a deep understanding of the challenges mid-sized businesses face, Chris launched VirtuousAI to close The Execution Gap, the costly distance between a company’s strategic goals and its ability to deliver. Under his leadership, VirtuousAI is redefining how businesses compete in the AI era: not by outspending the giants, but by out-executing them. His mission is to empower mid-market leaders to move faster, work smarter, and achieve measurable outcomes that drive sustainable growth.
Before founding VirtuousAI, Chris built and exited multiple successful ventures at the intersection of finance, supply chain, and enterprise software. His background blends deep operational knowledge with a visionary approach to automation and business intelligence, making him a trusted voice on the future of work, data, and strategic AI.
