Real Estate Reimagined: How Leaders are Adjusting to the New AI Landscape episode artwork

EPISODE · Mar 27, 2026 · 1H 1M

Real Estate Reimagined: How Leaders are Adjusting to the New AI Landscape

from The Mid-Market Multiplier · host VirtuousAI

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.

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.

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Real Estate Reimagined: How Leaders are Adjusting to the New AI Landscape

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This episode was published on March 27, 2026.

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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...

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