He Started as a Junior Analyst and Now Runs the Company and Its AI Strategy
James Drury, COO & Chief AI Officer, Cobone; Founder, Outriders.ai, Outriders.ai
Published October 8, 2026 · 32:04
Episode summary
James Drury joined Cobone, one of the original ecommerce companies in the Middle East, as a junior analyst a decade ago. Today he is its COO and Chief AI Officer, and he also founded Outriders.ai, where he builds AI operating systems for founders and executives. He explains why the real value in AI is in the system around the model, not the model itself, and how Cobone turned scattered AI experiments into systems that run the business.
What we cover
- Junior analyst to COO and Chief AI Officer
- Building AI operating systems with Outriders.ai
- The system around the model matters more than the model
- Turning scattered AI experiments into business systems
- Business resilience and crisis management with AI
- Why founders should hit failure as fast as possible