March 16, 2026
In this episode of The Mid-Market Multiplier, Chris Happ sits down with Todd Dooling, Chief Information Officer of Crow Holdings, to explore what practical AI leadership looks like inside a complex, growth-focused organization.
Todd shares his unique journey from application development to leading business technology, how Crow Holdings fosters a culture of empowerment, and why that matters to employees. The conversation also unpacks why incremental efficiency gains with AI will pay off significantly for companies in the long run, and what mid-market leaders must do to implement AI effectively, including securing top-down support to cultivating subject matter experts.
They also discuss the evolving impact of AI on workforce dynamics, and why curiosity, adaptability, and proactive learning will define the next generation of business leaders.
A must-listen for executives looking to move AI from experimentation to measurable impact.
Everybody's going out and getting their own version of whatever tool they think they want to do something. We want to be more thoughtful about it.
Todd Dooling is the Chief Information Officer of Crow Holdings (2018–Present), responsible for enterprise technology strategy, cybersecurity, modernization, data quality, and AI governance across the national Crow Holdings platform and the Crow Family. He has strengthened the firm’s risk posture, modernized cloud and identity architectures, elevated information governance, and deployed AI capabilities such as GPT Enterprise, Microsoft CoPilot, and Virtuous AI to improve complex business processes. Todd’s leadership emphasizes clarity, cross‑functional partnership, and disciplined execution, positioning technology as a driver of operational performance and institutional resilience.
Prior to Crow Holdings, Todd spent two decades (2003–2018) leading large‑scale technology, security, and transformation initiatives across real estate and financial services. He also served as a Senior Adjunct Instructor, teaching information systems, emerging technologies, and cybersecurity, sharpening his ability to translate complex technical concepts into strategic insights for executive teams and boards.
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.
