Podcast

A Founder's Life:

Balancing Entrepreneurship, Family, Health, & Fun​

Podcast

A Founder's Life:

Balancing Entrepreneurship, Family, Health, & Fun​

The Real Reason AI Isn’t Boosting Productivity - Charlie Cole - S5 - E4

In this episode, Charlie Cole, CEO of XGen.ai, shares his nonlinear path from math major → realestate.com analyst → Lucky Brand → Toomey → Samsonite → and now running an AI-driven commerce company.

Charlie breaks down how generative AI is reshaping personalization, data, search, and productivity and why the next era of commerce will be defined by agentic experiences, not traditional websites.

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Guest Info

Charlie Cole is the CEO of XGen AI and one of the most respected voices in global e-commerce, digital transformation, and AI-driven customer experience. With more than two decades of leadership across some of the world’s most recognized retail and consumer brands, Charlie has built a career at the intersection of technology, data, and human behavior.

Before joining XGen AI, Charlie served as Global Chief eCommerce Officer for Samsonite, where he oversaw digital strategy across more than 100 countries. He was also the Chief Digital Officer for Tumi, helping guide the company through its acquisition by Samsonite. Earlier in his career, he held executive and advisory roles at Lucky Brand, Assembled Brands, Schiff Nutrition, and several venture-backed startups.

Known for his ability to translate emerging technology into practical business outcomes, Charlie is now focused on leading XGen AI toward the future of agentic commerce—a more adaptive, personalized, intelligence-driven evolution of how consumers discover, shop, and interact with brands online.

Outside of work, Charlie is a father, a world traveler who has visited more than 90 countries, and an athlete with a deep commitment to personal health, sleep, and balance. His leadership philosophy centers on self-awareness, humility, and doing “everything you can today” as a measure of a life well lived.

Show Notes

About this Episode

In this episode, Charlie Cole, CEO of XGen.ai, shares his nonlinear path from math major → realestate.com analyst → Lucky Brand → Toomey → Samsonite → and now running an AI-driven commerce company.

Charlie breaks down how generative AI is reshaping personalization, data, search, and productivity and why the next era of commerce will be defined by agentic experiences, not traditional websites.


Highlights

Early Career: Math major → analyst → unexpected digital career.

Big Challenge: Navigating the chaos and speed of e-commerce growth.

Turning Point: Losing his mother, redefining meaning and adulthood.

Personal Growth: Fatherhood, self-awareness, health, and energy optimization.

Business Success: Leading XGen.ai and shaping the future of agentic commerce.

Future Vision: Safe personalization, AI-driven shopping, and empowering teams to embrace tech.

Resources

👤 Connect with Today’s Guest – Charlie Cole

LinkedIn: linkedin.com/in/charliecole

Email: [email protected]

Company: XGen.ai

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