Insurance Town

Heath Shearon

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. 1d ago

    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

  2. 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

  3. Jul 9

    A 90's Kid's Guide to Personal Branding

    In this episode of Insurance Town, we've got a Mayor Solo episode. No guest this week, just me and my fellow citizens of Insurance Town. Today, we're tackling a topic that I think has become way more complicated than it needs to be: personal branding. I'm going to challenge some of the biggest buzzwords in business and marketing today. What if "personal branding" is really just your reputation? What if authenticity is simply being true to yourself? What if networking is nothing more than making genuine friends? As a 90's kid, I don't think these ideas are new. I think we've spent the last twenty years creating new words for principles our parents were teaching us long before social media, LinkedIn, and personal branding became a thing. In this episode, we'll talk about how to intentionally build a reputation people trust, how to protect that reputation, why "fake it till you make it" is a dangerous philosophy, how to discover who you're uniquely called to serve, and why the strongest personal brands aren't manufacturedthey're built one promise, one relationship, and one act of integrity at a time. If you've ever wondered how to become known, trusted, and remembered without pretending to be someone you're not, I think you're going to enjoy this conversation.In this episode, you'll learn: Why your brand starts long before you ever have a "name brand"The difference between reputation and personal branding—and why it mattersWhy "fake it till you make it" may be holding you backHow being true to yourself is actually the easiest long-term branding strategyHow to identify the people you truly want to serveWhy trying to serve everyone weakens your reputationHow to define what you want to be known forWhy protecting your reputation sometimes means saying "no" to the wrong clientsHow one bad-fit customer can impact your culture, your team, and your future businessWhy networking is really about building genuine friendships, not collecting business cardsA simple way to talk about what you do without sounding like everyone elseHow to build a reputation that creates trust, referrals, opportunities, and long-term influenceSponsor Shout out: 1FortAI is changing the insurance industry, but the biggest opportunity isn't just automation, it's having proactive digital teammates that help your agency work smarter every day. Learn more at https://1fort.com. Canopy ConnectEliminate manual data entry and create a better client experience with Canopy Connect. Their technology allows prospects and clients to securely share insurance information in minutes. Learn more at https://usecanopy.com/heath. VIVA Virtual SolutionsLooking to grow your agency without adding unnecessary overhead? VIVA Virtual Solutions connects insurance agencies with highly trained virtual professionals who can help you scale your operations while delivering exceptional service. Learn more at https://vivavs.com.

  4. Jul 2

    Is your AI Reactive or Proactive?

    Most insurance agencies are still using AI like a search engine. They open ChatGPT. They ask a question. They get an answer. That’s useful. But it’s also reactive. The next generation of AI doesn’t wait to be told what to do. It monitors activity, organizes information, surfaces opportunities, flags missing data, drafts communications, and helps move work forward before anyone even asks. That’s the difference between using AI as a tool and working alongside an AI Digital Teammate. In this episode of Insurance Town, Heath Shearon sits down with Caleb Cramer of OneFort to explore how proactive AI is reshaping insurance agencies, commercial insurance workflows, and the future of agency operations. Together, they discuss why the conversation around AI needs to move beyond chatbots and prompts toward intelligent systems that actively support producers, account managers, and agency owners throughout the day. From commercial submissions and renewals to proposal generation, risk assessment, and customer communication, this episode provides a practical look at how AI is becoming an everyday teammate for insurance professionals. Most importantly, Heath and Caleb explain why the agencies that thrive over the next decade won’t replace people with AI. They’ll empower people with AI. Episode Chapters 00:00 — The Shift from Reactive AI to Proactive AI 02:11 — Meet OneFort: Your AI Digital Teammate 04:10 — Why Insurance Is Ready for Its Next Technology Leap 06:02 — Will AI Replace Insurance Professionals? 08:17 — AI-Powered Commercial Insurance Workflows 11:25 — Why Waiting on AI May Be the Biggest Risk 12:25 — The Rise of Proactive AI 16:44 — Lessons from Previous Technology Revolutions 18:23 — Thinking Beyond Today’s AI 22:15 — Why Human Connection Matters More Than Ever 27:36 — Personalization at Scale with AI 32:39 — Building Trustworthy AI for Insurance 37:22 — Why Humans Stay in the Driver’s Seat 43:24 — Security, Privacy, and Responsible AI 45:51 — Overcoming AI Skepticism Inside Agencies 50:07 — Commercial Insurance Renewals Reimagined 55:24 — Where Agencies Save the Most Time 58:35 — Simple Pricing and Fast Adoption For decades, insurance technology has waited for us to click the next button. The next generation won’t wait. It will organize, prioritize, recommend, draft, monitor, and help move work forward before anyone asks. That’s the promise of proactive AI. Not replacing insurance professionals. Creating AI Digital Teammates that handle the routine work so people can focus on building trust, advising clients, and growing their agencies. The future of insurance isn’t simply using AI. It’s working alongside it. Insurance Town Sponsors  1Fort AI – AI digital teammates built specifically for insurance agenciesCanopy Connect – One-click insurance data collectionVIVA Virtual Solutions – Insurance-trained virtual assistantsConnect with Caleb Cramer LinkedIn1fort on Linkedin

    Is your AI Reactive or Proactive?

  5. Jun 25

    From Family Agency to Insurance Business Rising Star | Kelly Smith

    In this week’s episode of Insurance Town, I had the privilege of sitting down with my good friend Kelly Smith. Kelly is one of those people who has truly lived the insurance industry from every angle. She grew up in a family agency, spent time at the front desk, worked in personal lines, commercial lines, agency operations, underwriting, carrier sales, and now helps independent agencies grow through her work with FirstChoice. What I loved about this conversation is that Kelly’s story is not just about insurance. It is about curiosity, hard work, education, family, leadership, and finding your place in an industry that can open a lot of doors if you are willing to keep learning. We talked about what it was like growing up in an independent agency, hiding under desks, messing with paper files, and learning the business from the inside out. Kelly shared how that agency background gave her a completely different perspective when she moved to the carrier side. She understood the urgency agents feel because she had sat in that seat herself. We also talked about her passion for education. Kelly shared a powerful story about being homeschooled, feeling behind academically when she started college, and how that experience fueled her desire to keep learning. Since then, she has earned multiple designations, completed her CPCU, and recently finished her MBA in insurance.  The best insurance professionals don't just master one job. They learn the entire ecosystem. Kelly's career took her from an independent agency to the carrier side and now to helping agencies grow through a network. Each step gave her a new perspective that made her more valuable. Whether it's earning a designation, volunteering with an association, mentoring others, or simply staying curious, investing in your education compounds over time. Your next opportunity often comes from something you're willing to learn today.  One of my favorite parts of the episode was our conversation about the next generation. Kelly’s daughter recently attended risk management camp at App State, and we talked about how important it is to show young people that this industry is bigger than home and auto insurance. There are opportunities in sales, underwriting, claims, marketing, leadership, technology, agency ownership, and so much more. Kelly also shared what it means to be recognized as one of Insurance Business America’s Rising Stars. Her humility really came through in this part of the conversation. She talked about being grateful for the opportunities she has had, but also wanting her story to encourage others, especially women and young professionals, to see what is possible in this business. 00:00 Welcome  02:35 Born Into Insurance   06:00 Agency vs. Carrier: Seeing Both Sides   09:10 Can We Attract the Next Generation?   12:20 From Homeschool to MBA   17:45 Why Education Creates Opportunity   23:45 Leadership Through Service   26:00 Becoming an Insurance Rising Star   30:15 Helping Independent Agencies Grow   31:45 The Truth About Insurance Networks   35:45 Connect with Kelly   36:50 Sponsors & Closing If you're looking for one of the most innovative events in the insurance industry, check out Insurance Fest, hosted by Insurance Business America. It's not your typical conference. You'll hear from industry leaders, discover what's next in insurance, and connect with people who are helping shape the future of our industry. It's also where today's guest, Kelly Smith, will be recognized as one of Insurance Business America's Rising Stars, an honor that's incredibly well deserved. After hearing her story, I'm sure you'll understand why she's being recognized as one of the industry's emerging leaders. I'll be there as well, speaking on stage and recording a live episode of Insurance Town with Christina Lucas from Google.  If you're planning to attend, come find us. Stop by, say hello, celebrate Kelly's accomplishment, and join us for the live podcast recording. I'd love to meet you in person. To learn more or register, visit Insurance Business America's Insurance Fest. I hope to see you there. SponsorsCanopy Connect1Fort AIViva  (00:00) - Welcome (02:35) - Born Into Insurance (06:00) - Agency vs. Carrier: Seeing Both Sides (09:10) - Can We Attract the Next Generation? (12:20) - From Homeschool to MBA (17:45) - Why Education Creates Opportunity (23:45) - Leadership Through Service (26:00) - Becoming an Insurance Rising Star (30:15) - Helping Independent Agencies Grow (31:45) - The Truth About Insurance Networks (35:45) - Connect with Kelly (36:50) - Sponsors & Closing

  6. Jun 18

    Are You Using the Right Technology to Scale Your Insurance Agency?

    In this week's episode of Insurance Town Podcast, I sat down with my good friend Mariah Gates. Mariah has become one of the insurance industry's leading voices on automation, technology adoption, and helping agencies work smarter. What makes her perspective unique is that it is grounded in service, faith, and a genuine desire to help others succeed. During our conversation, we discussed how agencies can stop viewing technology as a burden and start seeing it as a strategic advantage. Mariah shares practical advice for building an effective technology ecosystem, implementing AI without overwhelming your team, and creating processes that allow agencies to scale while maintaining strong relationships with clients. Whether you're just beginning your technology journey or looking to maximize the tools you already have, this episode is packed with actionable insights you can apply immediately. Main Topics Covered: • Mariah's journey into insurance technology and automation• How faith and servant leadership have influenced her career• The evolution of AI and its growing impact on insurance• Why agencies struggle to fully utilize their existing technology• Building a connected and scalable technology ecosystem• The role of CRM systems in agency growth and efficiency• Lessons learned from the industry's digital transformation during the pandemic• Practical first steps for implementing automation and AI• Avoiding technology overload and choosing the right solutions• Personal productivity and automating everyday life Key Takeaways: • The insurance industry still has significant room for growth when it comes to technology adoption.• Most agencies are only utilizing a fraction of the capabilities available within their current technology stack.• Successful agencies focus on creating connected workflows instead of collecting disconnected tools.• AI implementation works best when agencies start with specific business challenges rather than chasing trends.• Team buy-in is critical for successful technology adoption.• Leaders should focus on solving employee pain points before introducing new technology.• Technology should support relationships, not replace them.• Faith, service, and integrity can serve as powerful foundations for leadership and business growth.• Building within established technology ecosystems often creates better long-term outcomes than relying on standalone solutions.• Small automation improvements can create significant time savings in both business and personal life. Timestamps: (00:00) Welcome to Insurance Town(00:26) Sponsor spotlight and technology solutions for agencies(01:55) Introducing Mariah Gates(03:46) Mariah's background and path into insurance technology(05:17) Faith, leadership, and serving others(07:04) Helping others before building a business(09:11) The opportunity for greater CRM adoption in insurance(09:30) How technology is changing agency operations(11:14) The pandemic's role in accelerating digital transformation(13:45) Why agencies often underutilize their technology(17:28) Building an integrated tech stack that works together(22:11) Common mistakes agencies make when selecting technology(27:36) Practical ways to begin implementing AI(33:20) Getting employee buy-in for automation initiatives(39:12) Choosing technology based on business needs(45:08) Personal automation and productivity hacks(50:41) Final thoughts and advice for agency leaders(54:22) Where to connect with Mariah Gates Connect with Mariah Gates: LinkedIn: https://www.linkedin.com/in/mariah-gates Sponsors:Canopy ConnectMAV1Fort

  7. Jun 11

    Your Team Is Wasting Hours Every Week Doing This

    In this week's episode of the Insurance Town Podcast, I got to sit down with my good friend Carl Ziade, co-founder of Gaia, for a conversation about innovation, entrepreneurship, AI, and what it really takes to drive meaningful change inside an insurance agency. One of the things I appreciate most about Carl is that while he's a technologist at heart, he understands that technology alone doesn't solve problems. Process comes first. People come first. Technology simply helps great organizations execute better. Carl's journey is a fascinating one. As a Lebanese immigrant and Stanford-trained computer scientist, he didn't originally set out to build solutions for the insurance industry. In fact, Gaia emerged after lessons learned from a completely different startup venture. What followed was a relentless focus on listening to customers, solving real-world problems, and building tools that help insurance professionals eliminate repetitive work and focus on higher-value activities. In our conversation, we discuss: • Carl's entrepreneurial journey and path into insurance technology • The lessons learned from early startup failures and pivots • Why customer feedback should drive product development • The importance of strong business partnerships and company culture • Why process matters more than technology • Practical strategies for AI adoption inside insurance agencies • How Gaia's browser extension automates repetitive data entry • The power behind Gaia's "super copy" and "super paste" functionality • Change management and gaining team buy-in for new technology • What's next for Gaia and the future of data enrichment in insurance One of my favorite takeaways from this conversation is Carl's advice to start small. Too many agencies feel like they need a complete transformation overnight. The reality is that successful AI adoption often starts with one process, one workflow, and one win. Build momentum, create confidence, and then scale from there. If you've been wondering how AI can help your agency become more efficient without disrupting everything you're already doing, this episode is packed with practical insights you can apply immediately. Pull up a chair, grab your favorite beverage, and enjoy my conversation with Carl Ziade A special thank you to our sponsors for supporting the Insurance Town Podcast: • Canopy Connect, helping agents collect verified insurance information from prospects in minutes. • 1Fort, helping agencies streamline commercial insurance submissions and placement through AI-powered workflows. • MAV, helping agencies scale smarter sales and close more deals with Texting to quality quote and connect prospects with your producers We appreciate their support and their commitment to helping insurance professionals build better businesses.

  8. Jun 4

    What Separates This Growing Agency from Everyone Else?

    In today’s episode of Insurance Town, Heath sits down with Paul Riemer, CEO of Riemer Insurance Group and Panther Insurance. Paul shares how his agency has grown through a commitment to relationships, community involvement, strategic niche markets, and a willingness to embrace innovation while maintaining a personal touch. As a second-generation insurance professional, Paul discusses the lessons learned from starting at the ground level, building trust with clients, developing strong teams, and navigating today’s rapidly changing insurance marketplace. Key Topics Discussed: • Building a successful agency through relationships and community engagement • Opportunities emerging in challenging insurance markets • Growing through niche markets and specialized expertise • Creating a culture that attracts and retains great people • Balancing technology, AI, and personal service • Lessons learned from a family-owned insurance business Episode Timeline (0:01 - 1:57) Introduction & Sponsors  (2:19 - 4:13) Paul’s Introduction & Market Insights (6:04 - 8:01)Personal Background & Family Business (9:33 - 13:02)Challenges & Learning in Insurance (13:52 - 15:21)Agency Growth & Team Dynamics  (19:29 - 20:57)Community Engagement & Relationship Building (43:00 - 44:28)Innovation & Maintaining the Personal Touch (47:43 - 49:35)Conclusion & Contact Information Thanks to our Sponsors: 1fort AI Canopy Connect Mav The Sassy Happy

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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
    337
  • Rating
    Clean
  • Copyright
    © 2020 Insurance Town Media
  • Show Website
    Insurance Town

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