Why AI Pilots Fail with Jake Burns
September 23, 2026
Why do so many promising AI pilots fall apart when companies try to put them into production? In part one of this two-part episode of The Reality Layer, Dave Tobias sits down with AI Strategist, Technologist, and former AWS Executive in Residence, Jake Burns, to explore what separates AI experimentation from meaningful enterprise results. From overcoming legacy data challenges and controlling AI costs, to building internal expertise and earning employee buy-in, Jake shares what leaders need to get right, as AI moves from proof of concept to core business capability.
In this episode of The Reality Layer, host Dave Tobias sits down with AI Strategist, Technologist, and former AWS Executive in Residence, Jake Burns. Together, they analyze why enterprise AI initiatives stall after early success and how leadership can fix it.
With four decades of hands-on experience advising over 1,000 executive teams, Jake brings sharp builder intuition. He breaks down why building a proof of concept is easy, while engineering a secure, scalable production system trips up most organizations.
With four decades of hands-on experience advising over 1,000 executive teams, Jake brings sharp builder intuition. He breaks down why building a proof of concept is easy, while engineering a secure, scalable production system trips up most organizations.
For insurance carriers, legacy data and technical debt create friction. Jake explains why waiting for pristine data environments is a mistake. Instead, teams should build with current datasets and leverage AI to clean up legacy debt.
Technology is only half the battle. People and internal culture dictate ultimate success. Employees need a clear executive roadmap and personal incentives to support AI execution. AI is a capability multiplier designed to expand what your business can achieve.
Technology is only half the battle. People and internal culture dictate ultimate success. Employees need a clear executive roadmap and personal incentives to support AI execution. AI is a capability multiplier designed to expand what your business can achieve.
What You’ll Learn:
- Why enterprise AI proofs of concept succeed easily but stall during production scaling.
- How to build effective AI capabilities immediately without waiting years to fix legacy data.
- How execution gaps and scarce agentic talent convert promising builds into expensive failures.
- Why people, culture, and employee buy-in are fundamental to successful AI transformation
- How companies can combine existing industry knowledge with new AI skills instead of relying entirely on outside specialists
- Why executives should use AI themselves to develop a practical mental model of what the technology can and cannot do
- Why regulated industries such as insurance can adopt AI securely without treating compliance as a reason to delay
- How smarter model selection, architecture, and token usage can dramatically change the economics of enterprise AI
Jake Burns is an AI Strategist, Technologist, and former Executive in Residence at Amazon Web Services, where he spent nearly seven years as an Enterprise Strategist.
With four decades of technical experience, Jake has guided over 1,000 global executive teams through AI strategy, cloud adoption, enterprise optimization, and change management.
Today, Jake spends much of his time researching and building AI systems while advising executive teams on AI strategy and execution.
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