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

    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

    41 min

  2. 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

    44 min

  3. 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.

    39 min

  4. 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

    48 min

  5. May 28

    How Is AI Transforming Insurance with Data Accuracy and Efficiency

    In this episode of Insurance Town, I get to interview my good friend Casey Armstrong of Canopy Connect. We dive into the innovative ways Canopy Connect is revolutionizing data collection for insurance agencies. Casey shares insights on how their platform simplifies client interactions, enhances data accuracy, and integrates seamlessly into existing workflows. Join us for an engaging discussion on the future of insurance technology and how agencies can leverage these tools for growth and efficiency..In this episode:   Casey shares his journey with Canopy Connect from its inception in 2020 and how agency data collection has evolved.The simplicity of using QR codes and custom referral links to streamline prospect interactions.How Canopy Connect’s Trailhead feature offers flexible, choose-your-own-adventure insurance pathways.The real-world impact of instant loss runs and deck pages extracted directly from carriers’ systems.The role of AI in automating mundane tasks, freeing agents to focus on trusted advisory.Unique marketing strategies like limo rides and conference appearances to connect with customers creatively.The importance of human oversight in AI solutions to ensure accuracy and trust.Case stories illustrating premium increases through correct coverage and client advocacy.Practical tips for agencies new to Canopy Connect, including the ease of integrating it into current workflows.Casey’s heartfelt message on gratitude, technological progress, and the future of insurance.  Timestamps: 00:00 - Welcome to Insurance Town & Casey Armstrong intro 00:29 - Canopy Connect: The one-click solution for agencies 00:58 - The benefits of automation and the Trailhead feature 01:26 - AI for insurance: saving time and improving accuracy 02:23 - Exploring innovative marketing strategies and conference fun 03:00 - Casey’s background, biking stories, and Northwest Arkansas 07:28 - How Canopy Connect transforms prospect engagement 08:08 - The value of instant carrier data and loss runs 09:39 - Bringing human oversight to AI automation 10:34 - The manual effort saved by AI and data accuracy 12:23 - How deck pages from carriers eliminate errors 15:08 - Commercial accounts insights and loss history access 16:13 - Simplified onboarding for new users of Canopy Connect 16:53 - Embedding Canopy into existing agency workflows 20:16 - Real-world client stories: under-insured homes & premium impacts 24:28 - Trailhead: The flexible, customizable journey paths 28:23 - The speed and efficiency benefits of Canopy Connect 30:34 - Lead tracking and prospect management dashboard 36:37 - Creative marketing: conference limos & branded experiences 38:35 - Heartfelt messages to existing customers and prospects 42:08 - Casey’s call to action: harnessing technology for growth & successResources & Links:   Canopy Connect - Streamline client data collection and quoting1Fort AI - AI automation for insurance submissions and quotingMAV - Text messaging solutions for prospect qualification  Casey Armstrong on LinkedIn  Connect with Casey:   LinkedIn  Email: casey@usecanopy.com  Note: This lively and authentic discussion highlights cutting-edge solutions shaping the future of insurance. Whether you're an agent, agency owner, or industry innovator, Casey's insights will inspire your next move—embrace technology, improve efficiency, and grow your business with confidence.

    44 min

  6. May 21

    How can I use Content to Build Relationships and Grow my book?

    In this week’s episode of Insurance Town, I had the privilege of interviewing my friend Ema Roloff of Roloff Consulting. Ema and I dive deep into what it really means to lead in today’s digital world, especially in an industry built on relationships, trust, and communication. Ema shares her journey from education into digital sales and consulting, along with the lessons she learned during the COVID era that completely transformed the way she approached content, technology, and leadership. This conversation is packed with practical insights for insurance professionals, business owners, marketers, and anyone trying to navigate change without losing authenticity along the way. We talk about the power of educational content, why relationship-building still wins, how to use AI intentionally, and what it means to become a true digital leader inside your organization. If you’ve ever struggled with showing up online, wondered how to balance authenticity with innovation, or felt overwhelmed by the pace of change in business today, this episode is for you. Timestamps  00:00 – Introduction and episode overview  07:25 – Overcoming sales challenges through content and education  09:33 – Why relationship-building beats traditional sales tactics  11:45 – Long-term trust development and sales cycles  13:09 – Creating authentic, value-driven content for B2B success  22:06 – Change management and decision fatigue  24:24 – Moving from product-focused to problem-focused content  26:55 – The mindset of serving and educating through social media  31:36 – Balancing authenticity with experimentation and technology  36:31 – Intentional implementation of AI and tech solutions  46:33 – Avoiding hype cycles and focusing on purposeful growth  54:32 – Reflecting on COVID as a catalyst for growth and innovation  59:10 – Ema’s current work and how to connect with her  And as always, thank you to our amazing sponsors:  Canopy Connect  MAV  1Fort AI Be sure to subscribe, leave a review, and share this episode with someone in the insurance industry who could benefit from the conversation. ----------------------------------------------------------------------------------------------------------------------------------------------- The Sassy Happy- For all of your corporate gifting needs- contact Mysassyhappy@gmail.com for more information on all things client gifts, employee gifts, or personal gifting to your best friend or favorite person too. :)

    1h 3m

  7. May 14

    How Does Hyper-Responsiveness Set Top Insurance Agencies Apart?

    In this episode, Jay Wolfberg shares his remarkable journey from a small Connecticut town to leading a $32 million agency in Florida, and discusses his insights on scaling, client relationships, and franchise models in the insurance industry. Whether you're an aspiring agent or an industry veteran, Jay’s strategic approach to responsiveness and authenticity offers valuable lessons for growth and success. Timestamps 00:00 - Introduction and episode overview 02:24 - Meeting Jay Wolfberg and intro06:17 - The importance of selling on value versus price09:02 - How Jay figured out his agency’s unique value proposition 11:37 - Handling commoditized auto coverage and understanding customer needs & growth y to a $32 million book14:40 - The secret to hyper-responsiveness and proactive customer service 18:48 - Creating an effortless, customer-centric experience 22:41 - Building and leading a franchise with WeInsure 37:21 - The structure and benefits of the WeInsure39:00- how to find JAY 1Fort: AI for insurance agencies, automating submissions, quoting, and binding to save time and win more commercial PNC.Canopy Connect: The one-click solution for getting deck pages needed to quote prospects.MAV: AI-powered insurance expert managing unlimited leads with friendly text to qualify, quote, and connect prospects to agents.Resources & Links WeInsure GroupJay Wolfberg’s emailConnect with Jay Wolfberg LinkedInTwitter

    41 min

  8. May 1

    Am I Listening Enough to Close More Deals?

    In this episode, Tyler Brown shares a grounded and practical look at what actually drives success in insurance sales. Drawing from his upbringing and career journey, Tyler explains why authentic listening is still the most underrated skill in the business. He breaks down how emotional connection influences buying decisions, how to ask better questions, and why consistent follow-up separates top producers from everyone else. The conversation also explores how tools like AI, including platforms like Nova Intel, can sharpen sales performance without replacing the human element. If you are looking to improve close rates, build stronger client relationships, and bring more intention into your sales process, this episode offers a straightforward roadmap. A quick thank you to our sponsors who make conversations like this possible: 1Fort, Canopy Connect, and MAV. What You’ll Learn:  Why listening is more powerful than pitching in today’s sales environment  How emotional triggers influence buying decisions  Practical ways to improve your follow-up process  The art of asking deeper, more meaningful questions  How AI can support, not replace, strong sales habits  Why trust is built through honesty and transparency, not pressure Key Takeaways: Tyler makes a strong case that most sales problems are not pipeline problems, they are communication problems. Agents often talk too much, assume too much, and follow up too little. One of the biggest shifts discussed is moving from surface-level conversations to deeper discovery. When you slow down and truly understand what matters to a client, your recommendations become more relevant and your close rate improves naturally. Another important theme is consistency. Follow-up is not complicated, but it does require discipline. The agents who win are the ones who stay in front of prospects in a thoughtful and helpful way. On the technology side, AI is positioned as a tool for refinement. Whether it is helping analyze conversations, suggest better questions, or improve messaging, it gives agents an edge if they are willing to use it. Notable Quotes:  “If you listen long enough, people will tell you exactly how to sell to them.”  “People don’t buy policies, they buy peace of mind.”  “Follow-up isn’t about being pushy, it’s about being present.” Canopy Connect If you’re still chasing down dec pages and playing email tag with clients, you need to check out Canopy Connect. It’s a simple tool that lets your clients securely share their current insurance information in minutes. That means faster quoting, cleaner data, and a much better client experience. It takes friction out of the process, which is something every agency can benefit from. MAV Finding good people is one of the hardest parts of running an agency right now. MAV helps solve that by connecting you with trained, remote insurance professionals who are ready to step in and contribute. Whether you need help with service, sales support, or operations, MAV gives you a way to scale your team without all the traditional hiring headaches. 1Fort (1fort.ai) 1Fort is bringing AI into the insurance workflow in a practical way. This isn’t about hype, it’s about helping agencies move faster and make smarter decisions. From streamlining submissions to improving how you manage data and communication, 1Fort helps you operate more efficiently so you can spend more time where it matters most, building relationships and growing your book.

    33 min
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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
    333
  • Rating
    Clean
  • Copyright
    © 2020 Insurance Town Media
  • Show Website
    Insurance Town

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