AI isn’t just another software tool. It’s a transformation in how companies operate.

In this episode of Build Boldly, Pat Rodgers sits down with Santi Jaramillo, co-founder and co-CEO of Pragmatico, to discuss how mid-market and growing companies can move from experimenting with AI tools to becoming truly AI-native organizations.

Santi, a three-time founder with over $100M in exits, explains why most businesses are stuck in the “dabbling phase” of AI and what it takes to achieve 90% company-wide adoption and real productivity gains.

Together they talk about the leadership, technology, and cultural changes required to implement AI at scale. You’ll learn:

• Why leadership commitment is the most important driver of AI adoption
• How to create a clear AI vision and roadmap for your organization
• Why companies should standardize tools like ChatGPT or Claude
• The security risks of employees using personal AI accounts at work
• Practical “low-hanging fruit” AI use cases (meetings, email, financial analysis)
• Why early AI adopters will gain a massive competitive advantage

Santi also shares how organizations can use gamification, live training, and cultural change management to turn AI into an everyday productivity engine rather than another unused tool.

If you’re a business owner, executive, or team leader trying to figure out how AI actually fits into your company, this conversation will give you a practical roadmap to get started.

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