The Enlightened Agent

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.

In Episode 40 of The Enlightened Agent, Jason Keck sits down with Bill Devine and Jon Reynolds to explore how AI is moving from experimentation to real-world impact in insurance.

Bill and Jon share the story behind Naitiv and their approach to helping carriers and brokers accelerate AI adoption by rethinking workflows, modernizing data, and building on platforms like ServiceNow. As the industry shifts from ideas to execution, the goal is simple: close the gap between innovation and production.

The conversation dives into one of the biggest challenges facing insurance organizations today: AI is advancing rapidly, but most workflows, systems, and data structures were never designed for it. From underwriting and claims to onboarding and broker-carrier communication, they discuss why true transformation requires more than plugging AI into existing processes.

They also explore how ServiceNow evolved from an IT ticketing platform into a broader enterprise workflow engine, and why Naitiv sees an opportunity to help the insurance industry modernize operations with AI-first infrastructure and orchestration.

Together, they discuss:

• Why many AI initiatives struggle to move beyond proof of concept
• How outdated workflows and fragmented data slow innovation
• The role of ServiceNow in modern insurance operations
• Why AI should be embedded into workflows, not layered on top
• How agentic AI can reduce friction across broker and carrier interactions
• Why speed, orchestration, and governance all matter in regulated industries

If you are an agent, broker, carrier, or insurance leader trying to understand how AI will actually reshape operations and workflows, this episode offers a practical look at what comes next.

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In Episode 39 of The Enlightened Agent, Jason Keck sits down with Natasha Kiemnec for a candid, no-filter conversation about artificial intelligence, risk, and how the role of insurance professionals is evolving.

Natasha shares the story behind Lion Specialty and how she and her team built a modern brokerage focused on high-touch service, data, and thought leadership. As AI reshapes the industry, the goal is not just adoption, but rethinking how work gets done across underwriting, claims, and client service.

They explore the less-discussed side of AI, including emerging risks, regulatory considerations, and how carriers and brokers are beginning to adapt. From hallucinations and errors & omissions exposure to real-world underwriting use cases, the conversation highlights why a human-in-the-loop remains critical.

In this episode, they discuss:

• How AI is changing risk profiles across underwriting and claims
• Where AI introduces new exposures, including hallucinations and E&O risk
• Why redesigning workflows matters more than simply adopting AI
• How leading firms are using AI to compress weeks of work into hours

If you are an agent, broker, or insurance leader trying to understand not just the opportunity but the risk of AI, this episode offers a practical look at what’s changing and what to watch next.

Jason Keck sits down with Reghan Brandt for a candid, no-filter conversation about loss runs, operational complexity, and what it really takes to build in insurance today.

Reghan shares the story behind Loss Run Pro and how she turned one of the most painful, manual processes in commercial insurance into a scalable, automated workflow used by thousands of agencies. From fax machines and follow-ups to APIs and automation, the goal is simple: eliminate friction and get agents the data they need, faster.

They explore how AI is actually being applied across the industry, where it’s overhyped, and where it’s driving real impact. The conversation also dives into how modern agencies are thinking about build vs. buy, integrations, and creating more connected technology ecosystems.

Together, they discuss:

• Why loss runs remain one of the most complex and critical workflows in insurance
• How automation and APIs are reshaping agency operations
• Where AI adds real value vs. where it’s just noise
• The shift toward more connected, flexible tech stacks

If you are an agent, broker, or insurance leader looking to streamline operations and better understand how modern tools are changing the industry, this episode offers a practical look at what’s working and what’s next.

In the Series 4 kickoff of The Enlightened Agent, Jason Keck sits down with Ryan Hanley for a direct, no-filter conversation about artificial intelligence and what it means for insurance agencies right now.

Jason shares the vision behind Broker Buddha AI, a new enterprise-grade platform designed to unify CRM, task management, e-sign, service workflows, rating, loss runs, and more into a single AI-powered system integrated with major AMS platforms. After nine months of rapid development, the goal is simple: fewer systems, more flexibility, and faster innovation.

Ryan challenges the comfortable narrative around AI, arguing that transactional work will be automated and agencies must refocus humans on what they do best: building relationships, solving complex problems, and selling.

Together, they discuss:

• Whether AI replaces jobs or reshapes them
• Why agencies still need a secure core system of record
• The shift from bloated software bundles to modular tools
• How AI-driven development enables real-time product iteration

If you are an agent, broker, or insurance leader trying to understand what is hype and what is real, this episode offers a candid look at where the industry is headed and how to prepare.

On this episode of The Enlightened Agent, Broker Buddha CEO is joined by Tompkins Financial Vice President and Commercial Lines Manager, Kim Nevinger. Kim is responsible for the overall direction and management of the commercial lines service department, and as part of the agency’s senior leadership team, supports strategic initiatives across the organization. Kim has more than 30 years of experience in the insurance industry.

On this week's episode of The Enlightened Agent, Broker Buddha's CEO Jason Keck is joined by Sheri Weaver, Learning and Development Manager at HNI Risk Services. As a Learning & Development professional with a passion for collaboration and for creating memorable and meaningful learning experiences Sheri absolutely loves working with others and always seek to discover and encourage their strengths. Throughout her career, she has enjoyed the opportunity to be one of the first in line to welcome new talent and help craft their onboarding journey. From new talent onboarding through instructional design, training facilitation, project management and workflow management she has eagerly embraced the opportunity to have fun, empower others and weave unforgettable experiences into learning and development programs.

On this week's episode of The Enlightened Agent, Broker Buddha's CEO Jason Keck is joined by Lockton Chief Operating Officer and Chief Diversity Officer Brian Roberts. As COO for the Midwest, Brian is be responsible for operations and business development for Lockton’s regional hub, including Chicago, Cleveland, Green Bay, Memphis, Milwaukee, Nashville, Pittsburgh and St. Louis. A skilled people developer and coach, is also be responsible for attracting the best industry talent and maintaining Lockton’s position as the best place to work and do business in insurance.