Context Files: Scale GenAI Across Complex Work
Hosted by Kevin Dewalt
Fri, Mar 13, 2026
5:30 PM UTC (30 minutes)
Virtual (Zoom)
Free to join
Go deeper with a course

Fri, Mar 13, 2026
5:30 PM UTC (30 minutes)
Virtual (Zoom)
Free to join
Go deeper with a course

What you'll learn
Understand core shift behind context files
Build your first context file in 10 minutes
Design a scalable reasoning system
Why this topic matters
You'll learn from
Kevin Dewalt
Three decades building enterprise AI — from neural nets to GenAI
I’m Kevin Dewalt, co-founder of Prolego. For three decades, I’ve built and led enterprise AI systems, from neural networks at Stanford in the early 1990s to today’s production-grade GenAI platforms. In dozens of Fortune 500 engagements, I’ve seen the same pattern: organizations do not lack ideas. They lack focus, sequencing, ownership, and adoption discipline.
My work centers on imposing that discipline. Inside enterprise AI CoEs, I help leaders narrow to the few initiatives that matter, align stakeholders, secure funding, and ship production systems. Over time, this became a repeatable approach for creating focus and execution under pressure.
Career highlights
- Drove approval of $1–$10M annual enterprise AI budgets
- Architected AI strategies underpinning $100M+ board-level investment decisions
- Led dozens of AI strategy and engineering initiatives for Fortune 500 and highly regulated organizations, including Morgan Stanley, Citi, Bristol Myers Squibb, RTX, Bosch, FINRA, Lockheed Martin, Collins Aerospace, and others
- Trained 1,000+ senior executives through private institutional AI leadership programs
- Designed and facilitated executive AI workshops at Stanford, Carnegie Mellon, UC Berkeley, and MIT
- Early strategic investor in Palantir at IQT; supported deployment of its first AI product in the U.S. intelligence community
- 6x technology founder; investor in 35+ startups
- M.S. Engineering (AI), Stanford; #1 graduate, U.S. Coast Guard Academy
