Insurance Town

Heath Shearon
  • 4.8 (52)
  • Business
  • Updated Weekly

Welcome to Insurance Town! Your host is the Mayor of Insurance Town, Heath Shearon. After many years in different parts of the insurance world, Heath wants to share his experience with you. Join in on conversations with Heath and many of the friends he's made along the way. Insurance Town is a production of Insurance Town LLC! Find more info at http/://www.Insurancetownpodcast.com Music: "Mornin, Noon, and Nite" by Daddy Long Legs

  1. 5d ago

    Where do I even start when it comes to AI in my agency?

    In this weeks episode the Mayor talks with Dave Rose, an agency operator at Bolt and former Liberty Mutual and Travelers leader, about what independent agents can learn from captive carriers, how connected distribution works, and how agencies can start using AI without overhauling everything. Dave brings a practical, operator’s perspective from both the agency side and the tech side, with a focus on real-world implementation rather than hype.In this episode, they cover the process discipline of captive agencies, the power of referrals and centers of influence in the independent channel, and why AI adoption is more about solving specific pain points than chasing tools. They also preview Dave’s ITC session on building an AI-first agency plan in 30, 60, and 90 days. Timestamps 00:00 — Intro, sponsors, and welcome to Dave Rose 08:24 — What Bolt does as a connected distribution platform 10:25 — What Dave learned moving from captive to independent 12:40 — Why independent agency success depends on knowledge, not just choice 15:03 — Centers of influence and building referral pipelines 17:05 — Why branding and marketing matter in the independent channel 19:19 — Why Dave wanted to be both an agency operator and technology builder 20:16 — How Bolt tests technology from the agency side first 23:04 — Why AI vendors all sound similar and what actually matters 24:57 — Advice for technology vendors: think through the agency lens 27:00 — The difference between insurance-first technology and tech-first insurance 28:17 — ITC and the growing role of agents at the conference 29:36 — A real example of an agency owner unsure where to begin with AI 31:18 — Why the industry is still early in its AI journey 34:13 — Three AI myths Dave wants to challenge 36:02 — Why AI should support, not replace, relationship-driven work 38:36 — Dave’s ITC session: practical next steps for agencies 41:26 — Agent Day at ITC and the value-first approach 42:23 — Session title: The AI First Agency: Your 30-, 60-, and 90-Day Plan in 15 Minutes 46:03 — The origins of Bolt and its connected distribution mission 47:28 — How Bolt connects lead generation, quoting, binding, and servicing 49:31 — Who should talk to Bolt and who benefits most 51:29 — How to reach Dave and Bolt 52:40 — Why ITC is worth attending for independent agents 54:58 — Why ITC works because of its concentration of knowledge and conversation Sponsors:Canopy Connect1fortViva If you have not registered for ITC Vegas. Go check it out and use discount code : 1AGSPKSNB for $200 off

  2. Aug 27

    How do I close more prospects ?

    This week in insurance town Heath Shearon sits down with Martin Mashalov, co-founder of Gridpull, to unpack why buying more leads is not the same as getting more business. They dig into how appetite matching, renewal timing, and trigger-based prospecting can help agencies spend producer time more efficiently and improve conversion rates. Martin explains how his background in applied math and insurance analytics led him to build tools for finding better prospects, not just more prospects. The conversation stays practical throughout, with examples from restaurants, commercial real estate, and new business triggers. 00:00 - Welcome to the episode and the lead buying problem  05:22 - Why insurance complexity pulled him toward technology  09:55 - Modeling insurer risk and learning the agency and brokerage chain  12:04 - How lead buying became a prospecting problem  14:39 - Why volume alone does not fix lead performance  18:39 - What “appetite” means for agencies and carriers  20:29 - Restaurant examples and carrier appetite edge cases  27:17 - New business triggers as a smarter prospecting strategy  28:21 - Permits, hiring, and licensing as insurance signals  31:38 - Trigger stacking for stronger prospecting profiles  33:20 - Why Gridpull was built around a real workflow problem  34:08 - Where AI fits and where it should stay out of the way  39:30 - How Gridpull organizes renewals, contacts, and follow-up  42:43 - Using existing books of business for cross-sell opportunities  44:10 - Early conversion rate and revenue gains from Gridpool  47:40 - How Gridpull supports agencies beyond just software  48:13 - Contact options and demo availability  49:22 - Free trial, credits, and privacy considerations   Sponsors :CANOPY CONNECT1 FortVIVA

  3. Aug 20

    How Can I Maximize My Conference Experience?

    This week Drake Lawhead comes to visit us in Insurance Town to talk all things conference , and maximizing the conference experience. We get into what all goes into building a major industry event and how attendees can actually get value from showing up. They also dig into how ITC evolved from an investor-focused conference into a broader experience for agents, brokers, carriers, and the tech vendors serving them.We discuss why in-person networking still matters, how to prepare before a conference, and what makes ITC’s agent and broker programming different from a typical trade show.   00:00 - Welcome to Insurance Town and sponsor shoutouts  08:25 - What conference planning really looks like behind the scenes  09:36 - How conference teams handle complaints and reduce friction  11:42 - How attendees should prepare before a conference starts  13:25 - Why some people should attend with a plan and others should leave room for serendipity  15:46 - Why staying present beats taking conference-day Zoom calls  18:48 - Why in-person networking still beats digital connection  19:49 - How ITC’s app and meeting system help people connect fast  28:35 - Why insurance is a natural fit for technology and AI  31:09 - What ITC Agents attendees can expect from Tuesday through Thursday  33:43 - Expo hall, main stage, happy hours, and the closing concert  38:05 - Why ITC was built for introverts too  39:43 - Quiet zones, lounges, puppy park, and low-pressure networking  42:31 - How ITC borrows ideas from other conferences  45:01 - Why intentional networking matters more than just putting people in a room  46:45 - Why Drake enjoys the independent agency world  47:58 - Dates, location, and how to register  48:59 - ITC events around the world  50:49 - Final push to register and use the app  51:47 - Closing thanks and signoff   Thank you to my Sponsors:   Canopy Connect 1fort Viva Virtual Solutions

  4. Aug 13

    Should I give my clients my personal cell number ?

    In this weeks Episode, I got the chance to talk to my brother, my homie, my main man, Casey Nelson of Agency X and Eclipse Insurance. We talked about a major career shift, returning to the agency side with Eclipse Insurance, and why that move is giving him a new lens on what  works and what doesnt inside an agency. They also dig into Agency X, Casey and Jessica Holder’s upcoming behind the scenes podcast about fixing real agency problems in real time. Think, Reality TV meets VLog, meets Podcast, and all rolled into some entertaining and Educational Content built for insurance agencies.  A big part of the conversation centers on the tension between old school workflows, modern automation, and AI, plus how agencies can adopt technology without creating chaos. Let me be real , this one gets SPICY, QUICK!!  Timestamps 00:00 - Welcome to Insurance Town and sponsor rundown 02:25 - Casey joins the conversation and catches up with Heath 08:51 - Why agency owner alignment on process is non negotiable 09:46 - Paper workflows, printed emails, and missing documentation 14:07 - Why no insurance tech is truly ready out of the box 15:04 - Preparing clients for AI driven service changes 20:28 - Front door theory and getting everything into the ecosystem 22:24 - Why agents should stop using personal cell phones for business 24:14 - Relationship business vs order taker mentality 27:10 - The value of honest staff feedback on workflows 31:17 - How AI adoption has changed since the Zapier era 32:26 - Why agencies that resist tech risk falling behind 37:46 - AI fatigue and why younger generations may push back 39:21 - Why agencies should map pain points before buying AI tools 40:22 - Change one variable at a time and keep a baseline 41:38 - What is agency X 47:40 - Casey’s ITC speaking opportunity 49:10 - What Casey will talk about at ITC 50:42 - Why the agent and vendor halls at ITC are worth the trip 51:38 - ITC promo code details and closing thoughts 52:32 - Final thanks, future guest host plans, and signoff Sponsors:Canopy Connect 1Fort AIViva Virtual Solutions

  5. Aug 6

    Can Voice AI Transform the Insurance Customer Experience?

    This week in Insurance Town, I got to sit down with Francisco Lopes of Sonant.AI for a conversation about one of the fastest-growing technologies in the insurance industry: voice AI. Artificial intelligence has become one of the biggest topics in our business, but with all the excitement comes plenty of skepticism. Francisco and I discussed where voice AI has come from, why today's technology is dramatically different than the automated phone systems of the past, and how agencies can begin using AI in ways that improve both customer experience and operational efficiency. We also talked about the concerns many agency owners and employees have about AI replacing jobs. Francisco shared why he believes AI is best used to support people, not replace them, allowing agency teams to spend more time building relationships and solving complex client needs while automation handles routine conversations. Whether you're just beginning to explore AI or you're looking for practical ways to implement it in your agency, this episode offers valuable insights into where the technology is headed and what independent agencies should be doing today to prepare for tomorrow. Chapters 00:00 Introduction and episode overview 02:23 Francisco's background and journey from astrophysics to AI 08:01 Moving to Silicon Valley and the lessons learned building AI technology 12:00 How Sonant.AI found its niche serving independent insurance agencies 14:46 Overcoming skepticism about voice AI and changing perceptions in insurance 17:47 Why creating a great customer experience matters more than achieving technical perfection 21:56 Addressing concerns about AI replacing jobs and why AI should empower agency teams 28:50 The future of AI in insurance, agentic AI, and where agencies should begin 36:01 Practical advice for insurance agencies looking to implement AI today 38:00 How to connect with Francisco and learn more about Sonant.AISponsors:Canopy Connect-1Fort AIViva Virtual Solutions

  6. Jul 30

    The Future of AI in Insurance with Christina Lucas {LIVE}

    There are some interviews you enjoy... and then there are conversations you genuinely don't want to end. This was one of those. Recorded live from the iconic Santa Monica Pier during InsuranceFest 2026, I had the opportunity to sit down with Christina Lucas of Google Cloud, and what a fantastic conversation it turned out to be. While many people know Christina for her work at Google Cloud, what really stood out was her incredible journey. From leading teams across the United States to living and working around the world, her experiences have shaped a unique perspective on leadership, innovation, and the future of our industry. She shared lessons learned from different cultures, different organizations, and different stages of her career—and in doing so, taught all of us something valuable. Of course, we couldn't sit down with Christina without talking about artificial intelligence. We explored how Google Cloud is helping transform the insurance industry, why trust and security remain at the center of innovation, and how organizations can embrace AI in practical, meaningful ways. Rather than focusing on the hype, Christina brings a thoughtful perspective on how technology can empower people and create better outcomes across the insurance ecosystem. We also discussed her newly co-authored book, Artificial Intelligence in the Insurance Industry, where she shares practical insights into how AI is already reshaping underwriting, brokerage, customer experience, operations, and leadership. Whether you're just beginning your AI journey or looking to take the next step, her perspective is one every insurance professional should hear. This episode is packed with leadership lessons, technology insights, and plenty of laughs along the way. I had an absolute blast recording this one, and I think you're going to enjoy every minute of it. A huge thank you to Christina for taking the time to join us and for sharing her wisdom with the Insurance Town community. A special thank you to our amazing sponsors for making Insurance Town possible: 🏙️ Canopy Connect – The easiest way to collect verified insurance information from your clients in minutes. 🏙️ 1Fort – Helping insurance agencies leverage AI to streamline submissions, improve workflows, and create more time to serve clients. 🏙️ VIVA Virtual Solutions – Providing highly trained virtual professionals who help agencies scale efficiently while delivering exceptional service.

  7. Jul 23

    The Relay of information !

    In this weeks episode i interview my new friend Jerry Ye, we explore how AI is transforming the insurance industry through the lens of Jerry Ye, in this engaging episode. Learn about the practical applications of AI in streamlining workflows, enhancing client relationships, and the future agency model.   The journey of Jerry Ye into the insurance and AI space, including his background in machine learning and entrepreneurshipHow AI is helping agencies automate manual tasks like policy checks, renewals, and COI generationThe importance of integrating AI deeply into agency workflows versus superficial useThe myths and realities of AI replacing versus augmenting insurance agentsPractical tips for agencies to adopt AI, including buy versus build strategies and overcoming industry resistanceFuture vision: AI's role in reducing operational bottlenecks and enabling agents to focus on relationship-building  Time Stamps   00:00 - Introduction to the episode and guest Jerry Ye02:30 - Jerry's background in AI, entrepreneurship, and insurance07:15 - Stereotypes in insurance: sales and service myths10:45 - Why insurance remains resilient and adaptive13:30 - The impact of AI on insurance agency workflows16:40 - The role of call coaching and relationship building in sales19:50 - AI's future in automating operational tasks and deep system integration22:15 - The challenge of adopting AI in traditional, old-school agencies26:00 - Key bottlenecks in agency operations: renewals, policy checks, and more29:20 - The buy versus build debate in AI software adoption32:00 - How integrated AI solutions should work in agencies35:20 - Origin story of Relay AI and its mission37:00 - The agency of the future and strategic AI adoption40:00 - How to connect with Jerry and upcoming MAC Conference Sponsors!  Canopy Connect 1Fort Insurance AI Viva Virtual Assistants   Connect with Jerry Ye:   LinkedIn  Twitter

  8. Jul 16

    How to scale a family owned insurance agency.

    In this weeks episde here in Insurance Town I got to interview my friend Jackson Rollo. In this episode Jackson, president of Rollo Insurance Group, shares how a second-generation family agency achieved remarkable growth by embracing unorthodox strategies rooted in community focus, technological innovation, and strong culture. Discover how intentional investment in people and purpose can transform an agency into a leading industry force. Main Topics Covered:   The evolution and rapid growth of Rollo Insurance over the past five years, doubling its offices despite a 26-year historyThe agency’s dedication to community involvement, including volunteer programs that foster local relationshipsReinventing agency culture: Building trust, loyalty, and unconventional hiring practicesThe importance of niching versus community focus, with insights into their local-market strategies in ArkansasHow adopting technology and AI enhances human creativity and service, not replaces itBalancing profit, purpose, and team development within a family-owned businessThe mindset shifts necessary for agency owners to move from producer to leader  Timestamps: 00:00 - Welcome & overview of Jackson Rollo’s agency story 04:10 - How culture evolution fuels rapid growth 06:15 - Local market dominance through community focus & tech adoption 09:00 - Debunking niche-focused growth: Community first approach in Arkansas 11:45 - The role of technology and AI in empowering staff 14:30 - Building trust and loyalty through unconventional hiring 17:00 - Leadership mindset: Transitioning from producer to leader 20:30 - Balancing family legacy with modern agency scaling 23:45 - Developing staff & the importance of loyalty and character 26:50 - Personal branding and empowering individual agency staff 29:40 - Reinventing agency culture: From day one to long-term growth 33:10 - Embracing contrarian approaches to agency success 36:20 - The value of investing in people for sustainable growth 39:45 - How to develop a future-focused, innovative agency culture 43:20 - The impact of AI and technology on human creativity & problem solving 47:15 - The evolution of Jackson’s personal leadership & maturity 50:45 - Traits of team-building and loyalty seen in Jackson’s family business 54:50 - Managing local engagement while embracing technology 58:15 - Connecting with Jackson & resources for agency growth   Canopy Connect1FortViva

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About

Welcome to Insurance Town! Your host is the Mayor of Insurance Town, Heath Shearon. After many years in different parts of the insurance world, Heath wants to share his experience with you. Join in on conversations with Heath and many of the friends he's made along the way. Insurance Town is a production of Insurance Town LLC! Find more info at http/://www.Insurancetownpodcast.com Music: "Mornin, Noon, and Nite" by Daddy Long Legs

Information

  • Creator
    Heath Shearon
  • Years Active
    2020 - 2026
  • Episodes
    343
  • Rating
    Explicit
  • Copyright
    © 2020 Insurance Town Media
  • Show Website
    Insurance Town

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