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.