In Episode 43 of The Enlightened Agent, Jason Keck sits down with Ashley Bennett Jones, SVP of AI Risk and Advisory at Lockton, for a conversation about what AI actually means for risk, coverage, and the brokers caught in the middle of it all.

Ashley spent eleven years at Lockton and a stretch before that as an insurance coverage litigator. She has seen this industry from almost every angle. Now she is in a role that did not exist a couple of years ago, doing work the industry is only starting to realize it needs.

The conversation gets into why AI is not really creating new risk so much as turning up the volume on risk that was already there, and what that means for policies written before anyone had a clear picture of the exposure. They talk through the coverage Goldilocks moment, where AI was quietly included in existing policies until exclusions started appearing. They get into vendor supply chains, shadow AI inside companies, the HuggingFace incident, and what it looks like when an AI agent ends up in the D&O seat. None of it is theoretical anymore.

In this episode, they discuss:

• Why AI risk is mostly amplified existing risk, and what that means for current coverage
• The gap between a policy written twelve months ago and the exposure a company has today
• How vendor contracts are creating liability that most companies have not thought through
• What the HuggingFace incident means for companies relying on third-party AI tools
• Why "we can't because regulators" is still the wrong answer, and what to do instead
• How Lockton is walking clients through the AI risk conversation before the market forces it

If you are a broker, risk manager, or business leader trying to get your arms around what AI actually means for your coverage and your clients, this is the conversation to start with.

In Episode 42 of The Enlightened Agent, Jason Keck sits down with Bryan Falchuk, President and CEO of the PLRB, for a candid conversation about what AI actually means for the insurance industry when you are sitting at the center of it.

Bryan brings 25 years in P&C, a background spanning claims, operations, distribution, and specialty lines. Now he is leading an organization that has spent 75 years building a knowledge business, and watching AI start to ask the same questions his members used to pay him to answer. That is not a comfortable position, and he does not pretend otherwise.

They get into hallucination risk and how the design of a tool matters more than the model behind it, why a big chunk of the carrier market is still waiting for regulatory clarity that is not coming, and what it actually looks like to move forward anyway. The conversation keeps coming back to the same tension: the industry defaults to "we can't because," and the moment calls for something closer to "how might we."

In this episode, they discuss:

• Why AI is an existential question for knowledge-focused organizations like PLRB
• How to design AI tools that give the right answer, or say nothing, rather than a confident wrong one
• Why regulatory uncertainty is not a reason to stop moving
• What claims speed and accuracy mean for agents, brokers, and their clients
• The "we can't because" problem in insurance and what it costs the industry

If you work in claims, run a carrier, or sell coverage and want a ground-level read on where AI is creating real pressure right now, this one is worth your time.

In Episode 41 of The Enlightened Agent, Jason Keck sits down with Alex Bond, founder of FinPro and host of the Leadership in Insurance podcast, for a straight-talking conversation about what it actually takes to build an AI-ready organization and the people who make or break that effort.

Alex has spent six years at the center of insurtech hiring, placing talent across carriers, MGAs, and SaaS businesses at every stage. He brings a ground-level view of where AI adoption is stalling, who is getting ahead, and why the biggest gap right now is not technology; it is leadership.

They dig into what "AI experience" really means when you are hiring, why middle management is where technology adoption either takes hold or quietly dies, and what separates the companies that are moving from the ones that are still talking about it. The build versus buy debate gets a fresh look, too, now that prototyping is faster and cheaper than anyone expected.

In this episode, they discuss:

• What hiring managers should actually look for when screening for AI fluency
• Why middle management is the make-or-break layer for any AI rollout
• How startup mentality maps to AI openness and what signals to look for
• The re-skilling gap nobody wants to talk about
• Why build versus buy is becoming build and buy, and what that means for insurtech

If you are a founder, executive, or insurance leader trying to figure out who to hire, how to structure your team, and where the people risk really sits in an AI-first world, this one is worth your time.