On this episode of The Edge, host Tim Leman sits down with entrepreneur and former CEO turned executive coach, Santiago "Santi" Jaramillo. Santi shares the arc of his journey—from growing up in Cali, Colombia, to building Emplify, to coaching leaders—and how those experiences shaped his approach to leadership, culture, and now AI adoption. They explore the importance of inner work after achieving external success, and Santi opens up about learning to separate self-worth from productivity, as well as the power of leading from love rather than fear. They also dig into why AI is first a cultural transformation, not just a technical one.

Connect with Santi on LinkedIn and his website.

Key Takeaways:

The problem Emplify was solving: engaging the modern workforce (1:27)
The #1 driver of engagement: the manager relationship (6:25)
Santi's origin story: Cali, Colombia to the U.S. (8:38)
Santi's journey from driven entrepreneur to executive coach (10:20)
The challenge of achieving success and still feeling unfulfilled (12:09)
Introspection and focusing on the inner work (13:28)
Separating self-worth from productivity (15:55)
Shifting from fear-based to love-based leadership (20:00)
How Santi starts AI enablement with execs: "start from the work" (23:25)
AI as a fundamental shift (25:00)
Why AI adoption is a cultural problem, not just a technical one (32:15)
"Peak work magic": what great teams feel like (35:37)

Santiago Jaramillo on entrepreneurship, inner work, and AI transformation