Insurance Town

Networking Not Working, Live From InsuranceFest 2026

This episode is live from the Santa Monica Peir at Insurance Fest 2026. Sponsors: Canopy Connect -Making it easier for agencies to collect insurance information directly from clients and prospects, helping speed up the quoting process and improve the customer experience. Bind AI- An AI-powered digital teammate built to help insurance professionals automate repetitive work, increase efficiency, and give their teams more time to focus on the human side of the business. V!VA- Helping insurance agencies scale with trained virtual professionals who can support service, operations, marketing, and more giving your team additional capacity without sacrificing the customer experience.

Can I Scale My Insurance Agency Without Losing My Culture?

This week in Insurance Town, Mayor sits down with longtime friend and fellow insurance leader Heath Barnett, co-owner of Legacy, for a conversation about growth, culture, ownership, and building a business people actually want to be part of. Heath Barnett is an insurance agency leader and co-owner of Legacy. After beginning his career in the captive insurance world, Heath transitioned into the independent channel and helped build Legacy into a multi-state insurance organization. His leadership philosophy centers on developing people, creating opportunities for ownership, giving local leaders autonomy, and building an organization where professional success doesn’t have to come at the expense of family and the things that matter most. Heath’s story starts in Memphis, Texas, where he grew up around agriculture, small-town relationships, and a family Farmers agency. After working alongside his grandfather and eventually purchasing the agency, Heath began seeing opportunities beyond the captive model. That journey ultimately led him into the independent insurance world and to what has become Legacy—an organization that has grown to roughly 250 people across multiple states. But this episode isn’t simply about getting bigger. It’s about how you grow without losing who you are. Heath and Mayor talk about the importance of training agents to understand what they are actually selling instead of competing on price alone. They dig into what the captive world can teach independent agencies about carrier training and development, why Legacy intentionally recruits coaches and teachers, and why the right culture can become one of the strongest recruiting and retention tools an agency has. They also get into ownership, succession planning, producer autonomy, burnout, family priorities, faith, and creating an organization where people have the opportunity to build something of their own. If you’re an agency owner thinking about growth, recruiting, producer development, culture, or succession, there are plenty of nuggets in this one. Episode Timestamps 00:00 – Welcome to Insurance Town 03:21 – Meet Heath Barnett 09:27 – Leaving the captive model for the independent channel 10:34 – Rebuilding culture in the independent insurance world 15:43 – What Farmers got right about training and support 18:26 – Stop selling price and start understanding the product 21:54 – Why Legacy recruits coaches and teachers 29:19 – Burnout, family priorities, and faith at work 32:53 – The original vision for Legacy’s growth 36:54 – Why producers choose the Legacy model 41:41 – Ownership, succession, and protecting an agent’s book 43:42 – Why Legacy moved beyond the traditional last-name agency model 44:53 – Connecting with Heath Barnett and Legacy 45:45 – Legacy’s growing multi-state footprint 46:02 – What could be next for Legacy 49:19 – Texas football, Texas Tech, and the Longhorns 51:15 – Closing thoughts Learn more about Legacy at legacyinsurance1.com. Proud Partners of Insurance Town Canopy Connect Stop chasing down declaration pages and PDFs. Canopy Connect helps insurance professionals collect verified insurance information directly from prospects and clients in seconds, creating a faster and easier experience for everyone involved. Bind AI Formerly 1Fort, Bind AI is helping insurance organizations put AI to work as a digital teammate—supporting workflows, increasing capacity, and helping teams spend more time on the work that requires human judgment and relationships. V!VA Virtual Solutions V!VA helps insurance agencies build effective virtual teams by focusing on more than simply placing a VA. Their approach centers on processes, training, accountability, and helping agencies create measurable return on their investment. Insurance Town listeners can receive $1,000 off when getting started with V!VA Virtual Solutions. Thank you to our partners for supporting Insurance Town and helping us continue bringing real conversations, practical ideas, and stories from people doing the work across the insurance industry. One change I particularly like here is positioning the episode around the question, “How do you grow without losing who you are?” That feels very on-brand for Insurance Town and gives the entire episode a stronger through-line.

How do I grow my agency using Virtual Employees?

in this weeks episode, Heath Shearon sits down with Rob Lopez, CEO of V!VA, for a wide-ranging conversation about insurance, outsourcing, virtual assistants, and AI. Rob shares how his path from broadcast journalism and sports radio led him back into the insurance world, and why his focus has always been on building real departments not just filling seats. They also dig into what makes V!VA different: process-driven onboarding, bilingual support, nearshore staffing in El Salvador, and a consultative approach that helps agencies document workflows before adding talent. https://vivateams.com/insurancetown Timestamps 00:00 – Welcome, sponsors, and introducing Rob Lopez from V!VA 03:33 – Why Rob stays present in the industry 05:32 – Rob’s early life as an Allstate kid 06:30 – Broadcast journalism, the Houston Rockets, and a career shift 07:26 – The first life insurance claim that changed Rob’s perspective 07:55 – Hurricanes Katrina, Rita, and Wilma 08:44 – Distribution work, aggregators, and building agency networks 09:35 – Why aggregator margins eventually hurt the value proposition 10:29 – Rob’s sports talk and media background 12:30 – Why catastrophe work mattered more than commissions 14:53 – Rob’s father and front-line catastrophe response 17:37 – Delivering a claim check and overcoming fear at the kitchen table 18:43 – Why showing up during claims builds trust 20:40 – Heath and Rob discuss the mission behind insurance 22:32 – How Rob entered the virtual assistant space 23:43 – Hiring for impact, not headcount 24:39 – The story behind V!VA’s first hire 27:18 – How that first hire became part of V!VA’s origin story 29:13 – The evolution from “VA” to trained insurance team members 30:13 – Why checklists and SOPs are essential 32:03 – Using virtual assistants to document workflows 33:27 – Why Rob is willing to say no to the wrong client fit 36:01 – Cheap labor versus true partnership 37:26 – Building departments instead of relying on one person 41:06 – Why turnover is inevitable without documented processes 42:31 – The impact of losing a virtual assistant 44:21 – V!VA’s systems and strategy review process 45:48 – Quarterly check-ins and role alignment 47:12 – Virtual assistants, licensed agents, and career growth 49:17 – Why nearshore support can be effective for insurance agencies 51:06 – AI versus humans in the agency 53:30 – V!VA Front Desk and AI-powered communication 55:22 – AI for after-hours lead capture 56:48 – Cost savings, payroll, and E&O coverage 60:04 – How to contact Rob and access the Insurance Town offer 61:26 – The $1,000 setup credit for Insurance Town listeners Sponsors: Canopy Connect - get dec pages , gather information , meet your clients where they are Get a discount using my code !! 1fort.ai- it is AI for insurance agencies , save time, be more efficient and win more deals with 1 Fort AI Viva - see why more people are going to viva for near shore talent. And get a massive discount for being a listener of the show

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 Connect 1fort Viva If you have not registered for ITC Vegas. Go check it out and use discount code : 1AGSPKSNB for $200 off

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 CONNECT 1 Fort VIVA

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

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

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

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.

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

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

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.

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

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

• Chapters

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

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.

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

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 quoting 1Fort AI - AI automation for insurance submissions and quoting MAV - 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.

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. :)

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 intro 06:17 - The importance of selling on value versus price 09:02 - 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 book 14:40 - 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 WeInsure 39:00- 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 Group Jay Wolfberg’s email Connect with Jay Wolfberg LinkedIn Twitter