https://simplecast.com The Reality Layer There's a layer beneath every decision: the data, the insights, the truth on the ground. The Reality Layer explores how data, AI, and emerging technology are reshaping the way organizations operate, compete, and make decisions, industry by industry. Hosted by David Tobias, Chief Product Officer at Nearmap. This season, we start in insurance. Copyrights © 2026 All Rights Reserved by Nearmap en Wed, 23 Sep 2026 13:52:00 +0000 Wed, 23 Sep 2026 18:39:45 +0000 https://podcasts.fame.so/the-reality-layer The Reality Layer https://image.simplecastcdn.com/images/6a22931a-8733-45a4-ae8d-fa756192aa5d/0e3ecd7d-b737-4165-a7ca-bda2b1667bfd/3000x3000/a33a9620-b769-11f1-9e49-39f6ec1237ca.png?aid=rss_feed https://podcasts.fame.so/the-reality-layer episodic There's a layer beneath every decision: the data, the insights, the truth on the ground. The Reality Layer explores how data, AI, and emerging technology are reshaping the way organizations operate, compete, and make decisions, industry by industry. Hosted by David Tobias, Chief Product Officer at Nearmap. This season, we start in insurance. Nearmap false https://feeds.simplecast.com/oBn0BtfM Insurance, insurance quotes, House insurance, AI in Real Estate, Geospatial Intelligence, AI in architecture, Structural damage, AI analytics, architecture, modern construction, Property Intelligence, aerial photogrammetry, aerial imagery, GIS geographic David Tobias team@fame.so 703rz371 Why AI Pilots Fail with Jake Burns 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.

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.


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.

If you enjoyed this episode, make sure to subscribe, rate, and review it on Apple Podcasts, Spotify, and YouTube Podcasts. Instructions on how to do so are here.


Episode Resources:


]]> Wed, 23 Sep 2026 13:52:00 +0000 team@fame.so (Nearmap) https://podcasts.fame.so/the-reality-layer 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.

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.


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.

If you enjoyed this episode, make sure to subscribe, rate, and review it on Apple Podcasts, Spotify, and YouTube Podcasts. Instructions on how to do so are here.


Episode Resources:


]]> Why AI Pilots Fail with Jake Burns Nearmap 00:20:48 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. 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. commercial property risk modeling, how can ai improve commercial real estate underwriting?, convective storm risk assessment, property risk assessment tools, why do ai pilots fail in insurance carriers?, property intelligence, high-frequency aerial imagery, how to turn aerial imagery into decision-ready claims data?, the reality layer podcast, how can carriers move from reactive claims to prevention-first insurance?, ai-ready roof geometry analytics, why ai pilots fail in enterprise, property condition and cost analytics, property claims modernization, property level truth data, macro to micro property risk, weather probability modeling for capture, force multiplier for human expertise, what are the top property intelligence platforms for insurers?, impactresponse emergency monitoring, proactive property loss prevention, high-resolution geospatial capture, proprietary llms for insurance carriers, how does high-frequency property data reduce claim cycle times?, regulated industry ai compliance, proactive risk mitigation vs reactive claims, ai-driven change detection, post-catastrophe aerial capture, disaster risk and spatial hazard analytics, p&c underwriting precision, ground truth data, automated underwriting accuracy, built environment resiliency, catastrophe loss trend analysis, what is property intelligence in p&c insurance?, climate risk and severe weather modeling, enterprise ai decision-making tools, digital truth in insurance, property intelligence platform, aerial property change detection, time travel imagery in risk modeling, rapid catastrophe response insurance, building materials data analytics, carrier solvency and risk management, mitigating climate-induced loss volatility, tornado and hailstorm loss analytics, agentic ai in insurance workflows, how can aerial data replace manual boots-on-the-ground inspections?, p&c insurance thought leadership, moving ai prototypes to production false full 1 81znk4k1 Trailer



]]> Wed, 23 Sep 2026 11:08:00 +0000 team@fame.so (Nearmap) https://podcasts.fame.so/the-reality-layer



]]> Trailer Nearmap 00:01:04 Welcome to The Reality Layer, a podcast exploring the data, signals, and real-world insights shaping the future of insurance and the built environment. Hosted by Dave Tobias, Chief Product Officer at Nearmap, each episode brings together executives and experts who are closest to the data and the decisions that matter. From underwriting and claims to catastrophe response and policyholder experience, discover what the data actually shows and how it can shape what’s possible. The Reality Layer is brought to you by Nearmap. Subscribe now and join us for The Reality Layer. Welcome to The Reality Layer, a podcast exploring the data, signals, and real-world insights shaping the future of insurance and the built environment. Hosted by Dave Tobias, Chief Product Officer at Nearmap, each episode brings together executives and experts who are closest to the data and the decisions that matter. From underwriting and claims to catastrophe response and policyholder experience, discover what the data actually shows and how it can shape what’s possible. The Reality Layer is brought to you by Nearmap. Subscribe now and join us for The Reality Layer. false full 0