Ep 36: Kim Nevinger, Vice President and Commercial Lines Manager at Tompkins Financial

Ep 41: Alex Bond on Hiring for AI, Startup Mentality, and Who Gets Left Behind

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.

Ep 40: Bill Devine & Jon Reynolds on Moving AI from Hype to Production

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. ‍ ‍

Ep 39: Natasha Kiemnec on AI Risk, Underwriting, and Why the Human Still Matters

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.

Ep 38: Reghan Brandt on Loss Runs, Automation, and Building in the Age of AI

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.

Ep 37: Broker Buddha AI + Ryan Hanley on the Future of the Insurance Industry and AI

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.