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#015: AI Strategy for Mid-Market CEOs: How to Start, Scale & Succeed Without Getting Left Behind | Chris Happ

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A conversation with Chris Happ of Virtuous AI

Is AI overwhelming your mid-market business? You’re not alone. In this unfiltered episode of CEOs Unscripted, host Jane Gentry sits down with Chris Happ, CEO of Virtuous AI and serial entrepreneur, to break down exactly how mid-market CEOs should approach AI strategy—without the tech jargon or corporate bureaucracy.

 

What You’ll Learn:

 

✅ Why AI is a STRATEGIC initiative, not an IT project
✅ How to identify the right business problem to solve with AI first
✅ The MIT study revealing why 95% of Fortune 500 AI pilots fail
✅ Why mid-market companies have a competitive advantage over enterprise
✅ How to manage AI as a change initiative (and avoid employee resistance)
✅ Real case studies: inventory optimization, workflow automation, and BI transformation
✅ The critical mistake of “bolting on” AI tools that create more silos
✅ How to protect your competitive advantage and proprietary data
✅ Why you should never wait to start experimenting with AI

 

Key Takeaways:

 

🔹 Start with ONE meaningful business problem (growth, profitability, or retention)
🔹 AI can clean your dirty data BEFORE you even begin analysis
🔹 You don’t need a massive budget—nimbleness is your superpower
🔹 Think “revenue per head” metrics (target: $1M per employee)
🔹 Avoid the subscription trap—consolidate around strategic platforms
🔹 Your AI strategy should be owned by the CEO, not delegated to IT

 

Perfect For: Mid-market CEOs, founders, business leaders navigating digital transformation, operations executives, and anyone feeling overwhelmed by the AI landscape.

 

Timestamps:

0:00 – Introduction: Why AI is overwhelming mid-market CEOs
2:34 – The MIT study: 95% of Fortune 500 AI pilots fail
5:38 – AI as a change initiative, not just technology
8:59 – Why mid-market CEOs have the advantage
12:33 – Predictive vs deterministic AI explained simply
15:48 – Start with a business problem, not the technology
19:10 – Case study: AI-powered inventory optimization
21:42 – The dirty data problem and how AI solves it
27:09 – Common mistakes and opportunities
33:35 – The subscription model trap killing mid-market budgets
40:18 – AI for business intelligence and real-time reporting
44:44 – Critical cautions: protecting your competitive advantage
49:58 – What happens if you need to switch vendors?
55:32 – Final takeaways and next steps

 

Resources Mentioned:

 

  • MIT Fortune 500 AI Study
  • Virtuous AI Platform (BAYO – Business Automation Intelligence & Outcomes)

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Episode Guest

Guest: Chris Happ is the CEO of Virtuous AI and a proven mid-market CEO who has successfully sold multiple companies. He specializes in helping businesses implement AI strategically without the enterprise complexity.

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ABOUT JANE GENTRY

Jane Gentry has had a successful 30-year career as a CEO, Business Consultant, Executive Coach, and Keynoter. Jane formed her practice in 1999 and since then has partnered with her clients to improve growth, profitability, client retention, employee retention, leadership capabilities and business value.

Jane leverages strategies including the proprietary Value Blueprint to enable business owners and leaders to successfully create healthy organizations, plan for succession or sell their businesses for the highest possible market value. Jane is considered one of the top voices in leadership and sales.

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CEOs UNSCRIPTED

Bi-weekly podcast by mid-market CEOs for mid-market CEOs

Welcome to CEOs Unscripted, the podcast where real talk drives real growth and delivers real results for mid-market leaders. Each episode offers an unfiltered, behind-the-scenes look at the wins, the losses, and the playbooks shared by CEOs, founders, and executives. Grab a seat and join us for unscripted, honest conversations about what it takes to lead, grow, and scale in today’s business landscape. 

no fluff. no jargon.