The Mid-Market Multiplier

The Mid-Market Multiplier

The Mid-Market Multiplier with Chris Happ is the go-to podcast for mid-market CEOs who want to turn AI from buzzword to business value. In each fast-paced episode, Chris Happ, CEO of VirtuousAI, sits down with industry leaders to tackle high-value questions that cut through the hype and get straight to the “how.” Expect thought-provoking conversations, real-world examples (failures included!), and practical strategies you can apply immediately. If you’re a mid-market senior executive ready to adopt AI strategically and unlock growth, this podcast is your multiplier.

Episodes

March 26, 2026 61 mins

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...

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Mark as Played

In this episode of The Mid-Market Multiplier, we sit down with multi-time founder Kate Boyer as she shares the entrepreneurial journey behind building the Anatomie brand and the operating principles that helped her scale. Kate emphasizes that strong core values, grassroots marketing, and personal customer relationships are foundational to durable growth—and that speed in customer service is a direct signal of respect for the custom...

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Mark as Played

In this episode of The Mid-Market Multiplier, we sit down with Dina Belon-Sayre, President of StayPineapple, to explore how AI is reshaping the future of hospitality. From hyper-personalized guest experiences to smarter operations and more agile decision-making, AI is opening new doors for mid-market hotel brands ready to innovate.Dina shares how StayPineapple thinks about customer delight, the role of data in crafting bespoke stay...

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Mark as Played

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