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
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August 20, 2026Episode 34551 min
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
August 13, 2026Episode 34453 min
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 AI Viva Virtual Solutions
August 6, 2026Episode 34341 min
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.AI Sponsors: Canopy Connect- 1Fort AI Viva Virtual Solutions
July 30, 2026Episode 34238 min
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.
July 23, 2026Episode 34135 min
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 entrepreneurship How AI is helping agencies automate manual tasks like policy checks, renewals, and COI generation The importance of integrating AI deeply into agency workflows versus superficial use The myths and realities of AI replacing versus augmenting insurance agents Practical tips for agencies to adopt AI, including buy versus build strategies and overcoming industry resistance Future 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 Ye 02:30 - Jerry's background in AI, entrepreneurship, and insurance 07:15 - Stereotypes in insurance: sales and service myths 10:45 - Why insurance remains resilient and adaptive 13:30 - The impact of AI on insurance agency workflows 16:40 - The role of call coaching and relationship building in sales 19:50 - AI's future in automating operational tasks and deep system integration 22:15 - The challenge of adopting AI in traditional, old-school agencies 26:00 - Key bottlenecks in agency operations: renewals, policy checks, and more 29:20 - The buy versus build debate in AI software adoption 32:00 - How integrated AI solutions should work in agencies 35:20 - Origin story of Relay AI and its mission 37:00 - The agency of the future and strategic AI adoption 40:00 - How to connect with Jerry and upcoming MAC Conference Sponsors! Canopy Connect 1Fort Insurance AI Viva Virtual Assistants Connect with Jerry Ye: LinkedIn Twitter
July 16, 2026Episode 34059 min
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 history The agency’s dedication to community involvement, including volunteer programs that foster local relationships Reinventing agency culture: Building trust, loyalty, and unconventional hiring practices The importance of niching versus community focus, with insights into their local-market strategies in Arkansas How adopting technology and AI enhances human creativity and service, not replaces it Balancing profit, purpose, and team development within a family-owned business The 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 Connect 1Fort Viva
July 9, 2026Episode 33927 min
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 manufactured they'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 matters Why "fake it till you make it" may be holding you back How being true to yourself is actually the easiest long-term branding strategy How to identify the people you truly want to serve Why trying to serve everyone weakens your reputation How to define what you want to be known for Why protecting your reputation sometimes means saying "no" to the wrong clients How one bad-fit customer can impact your culture, your team, and your future business Why networking is really about building genuine friendships, not collecting business cards A simple way to talk about what you do without sounding like everyone else How to build a reputation that creates trust, referrals, opportunities, and long-term influence Sponsor Shout out: 1Fort AI 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 Connect Eliminate 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 Solutions Looking 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 .
July 2, 2026Episode 33854 min
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 agencies Canopy Connect – One-click insurance data collection VIVA Virtual Solutions – Insurance-trained virtual assistants Connect with Caleb Cramer LinkedIn 1fort on Linkedin
June 25, 2026Episode 33740 min
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. Sponsors Canopy Connect 1Fort AI Viva (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
June 18, 2026Episode 33644 min
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 Connect MAV 1Fort
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