Michael Ley on Agency Networks, Tech Stacks, and the HawkSoft Purple Cow | Connected Conversations in InsuranceIn this episode of Connected Conversations in Insurance, Ray Huang sits down with Michael Ley, Director of Network Relations at HawkSoft, to talk about what agency networks and aggregators are doing to stand out and deliver real value beyond commission splits.Michael shares his journey from a family-owned agency to HawkSoft and breaks down what agencies should look for before joining a network—from book ownership and carrier access to contract terms, transparency, and technology investments.They also dive into the modern agency tech stack, why the AMS is at the center of it all, and the tools helping agencies work smarter, including CRM, texting and VoIP, e-signatures, and streamlined intake solutions.Plus, Michael talks about HawkSoft’s customer-first “Purple Cow” philosophy and wraps things up with a fun travel-themed round of “Where Would Michael Sit?”0:00 Networks Look Alike00:46 Meet Michael Ley01:37 What Network Relations Means03:23 From Teacher to Agent06:01 Networks vs Associations06:33 Network Pain Points10:35 Agency Network Checklist15:27 Tech Stack Talk17:28 Open APIs and Data Ownership21:35 Must Have Agency Tools29:15 Purple Cow Branding32:35 Culture and User Community34:10 Travel Game Setup34:54 Aisle vs Window Debate35:47 Bathroom Row Stories36:47 Family Travel Tradeoffs37:10 Accidental Private Jet38:02 Subway Seat Strategy39:42 Rental Shuttle Tactics41:19 Doctor Waiting Room Picks41:53 Conference Room Power Seats43:16 Movie Theater Sweet Spots44:43 Best Seats in the Stadium47:39 Airplane Selfie Side Eye49:28 Season Wrap and Sponsor

Nick Berry on TotalCSR, Microlearning, and Unhinged Insurance Marketing | Connected Conversations in InsuranceIn this episode of Connected Conversations in Insurance, host Ray Huang welcomes former co-host Nick Berry back to the show to share what he’s been up to since leaving Canopy Connect, including his new role as head of marketing at TotalCSR. Nick explains how TotalCSR helps agencies find, assess, and train talent across personal lines, commercial lines, and health and benefits, including license tracking and a microlearning app designed to reinforce knowledge retention—especially for complex commercial topics. They discuss common resistance to training, the need for ongoing skills checks, and how staying sharp builds trust as a “trusted advisor.” Ray and Nick then shift to marketing, emphasizing outcome-driven ads, creative that doesn’t look like ads, long-form copy, memes, and delivering value to local audiences rather than relying on direct “get a quote” messaging.00:00 Career With Cool People00:41 Podcast Welcome Back02:27 Nick Joins TotalCSR05:17 What TotalCSR Does07:16 Microlearning For Retention09:34 Canopy Connect Ad Break10:38 Custom Learning Paths13:19 Training Resistance And Trust15:02 Golf Practice Analogy17:23 Insurance Mustache Game20:49 Mayhem Ad Love21:07 Guessing Celebrity Jingle22:29 Progressive and Farmers Faces23:44 Canopy Connect Pitch24:49 Top of Funnel Marketing27:36 Unhinged Ads That Work32:26 Value First Local Ads36:06 Marketing Is Everything38:49 Wrap Up and Where to Find39:53 Final Canopy Connect Outro

Peter Wood on Mentorship, Community, and Collaboration in Insurance | Connected ConversationsPeter Wood didn't find insurance. Insurance found him. In this episode, Carrie sits down with Peter, agency owner at Kraken Insurance Services based in Chandler, Arizona, to talk about what it really takes to build a thriving agency, a strong community, and a mentorship culture that actually works.Peter shares how Kraken grew from around $5,000 a month in commissions to $350,000 in just 18 months, why he believes your problems are never as unique as you think, and the hard truth he has had to accept about helping people who are not ready to be helped. He also gets into what makes the Winning at Insurance Facebook community different, why listening matters more than talking in this business, and the three pieces of advice he gives every agent whether they are brand new or years into their career.If you have ever felt like you wanted to help someone more than they wanted to help themselves, or wondered whether the grass is really greener at a higher comp rate, this one is for you.00:00 Insurance Found Me00:55 Meet Peter and Kraken01:30 From Copiers to Captive03:26 Joining Kraken Growth06:07 Nationwide Footprint Event07:25 Collaboration Over Competition10:06 Peer Learning Communities11:32 Value Without Expectation12:51 Fact Finding Sore Thumb14:20 Coaching With Parma16:51 Feedback That Stings18:54 Building Group Culture20:21 Value Without Expectation21:40 Mentorship Learning Curve24:22 Book Recommendations for Leaders28:35 Listening to Understand31:31 Canopy Connect Ad Break32:37 Advice for Agents33:03 Mentors and Red Flags36:47 Compensation vs Support39:58 Closing and Outro

Austin Panter on Client-First Tech, Canopy Connect, and Using AI Without Losing the Human Touch | Connected ConversationsIn this episode of Connected Conversations, Canopy Connect host Carrie Thornbrugh speaks with Austin Panter of Kevin Panter Insurance in Blue Ridge, Georgia, about modernizing agency operations by adopting technology that prioritizes client convenience. Austin shares how his agency uses Canopy Connect as a secure, encrypted intake link to quickly gather dec pages and verified policy data, reducing manual scanning and duplicate entry, and how clear communication helps overcome occasional security concerns or internal resistance. He highlights a tech stack including HawkSoft, Risk Advisor, and AI tools like PowerBroker AI for comparing policies and improving efficiency, while cautioning against over-automation that removes relationships from a relationship-driven business. Austin explains that insurance is a “noble profession” focused on helping clients in crises, and closes with advice to always do what’s right for the client.00:00 AI and Agency Change00:42 Podcast Welcome and Guest Intro01:36 Austin’s Path Into Insurance03:17 Client First Tech Philosophy04:18 Canopy Connect in Practice08:11 Building a Modern Tech Stack09:25 Ad Break Insurance Intake10:29 Real World Wins With Tech12:34 Handling Objections and Security16:43 Future of Insurance and AI Tools19:09 Ad Break 10 Second Handshake20:15 Balancing Automation and Relationships24:57 Why Insurance Matters Most29:26 Doing the Right Thing Closing31:13 Final Thanks and Outro Ad

Casey Nelson on SOPs, Front Door Theory & Content as a Growth Differentiator | Connected ConversationsCasey Nelson joins Carrie Thornbrugh for the Connected Conversations season finale to talk about why agencies struggle with tech and operations—and how to fix it. He breaks down Catalyit’s role, the three common “origin stories” that lead to messy systems, and why solid SOPs, training, and accountability actually make tech work.Casey also shares his “front door theory” for standardizing how requests come in (so your data isn’t a mess), plus some practical tips for getting your team on board with change. They wrap with a look at why content will be a key differentiator as tech becomes more commoditized—and a simple upgrade: ditch the generic “contact us” and use structured forms with automated replies.00:00 Why Tech Fails00:41 Season Finale Intro01:48 Meet Casey Nelson04:33 From Teaching to Insurance08:28 Teachers as Sales Pros11:15 Canopy Connect Ad Break12:22 Why SOPs Break Down12:48 Three Agency Origin Stories16:05 Resistance and ROI Objections17:57 Front Door Theory22:37 Accountability and Change25:10 Implementation at Canopy25:45 Driving Full Adoption26:12 Getting Team Buy In27:49 Pain Points Before Tools30:20 Avoid Shiny Object Traps31:40 Canopy Connect Ad Break32:47 Content As Differentiator36:59 Wrexham Story Marketing39:39 Simple Content Ideas41:16 Fix Your Contact Flow43:26 Wrap Up And Final Plug

Dylan DiMarchi on Premium Lock: A 3-Year Price Guarantee for Homeowners Insurance | Connected Conversations in InsuranceRay Huang hosts Dylan DiMarchi, co-founder of Eventual, to discuss the volatility in U.S. homeowners insurance since COVID and how Eventual’s Premium Lock offers a three-year price guarantee as a supplement to standard one-year admitted homeowners policies. Dylan explains how home insurance premiums rose nationally in the high teens (about 15–18%) in 2022–2024, with current growth around 12–13%, while state trends differ—Florida decelerating and California accelerating (around 19–20%) amid availability challenges. He outlines how Premium Lock predicts a home’s premium path over three renewals and reimburses homeowners if premiums exceed the guaranteed threshold, using data, modeling, and agent-submitted quoting information. They also cover agent benefits like differentiation, improved retention, reduced service workload, and how agents can get appointed and quote quickly via a portal and Canopy Connect integration.00:00 Insurance Costs Surge00:40 Podcast Welcome01:37 Dylan's Background03:20 Premium Lock Explained04:08 Market Volatility Trends07:24 How Pricing Is Predicted13:00 Guarantee And Payouts14:09 Canopy Connect Ad Break15:15 Agent Challenges Today20:19 Selling Premium Lock22:32 Product Mechanics Clarified24:38 Canopy Connect Automation25:42 Eligibility And Renewals29:21 Agent Onboarding Steps30:56 Hot Takes Segment35:10 Closing Remarks35:43 Final Canopy Connect Outro

Victoria Ardito on Insurance Education, Relationship-Driven Selling & InsurTech | Connected ConversationsIn this customer-focused episode of Connected Conversations, host Carrie speaks with Victoria Ardito, a personal lines insurance advisor at Insurance Office of America with 14 years in the industry. Victoria shares how she entered insurance by walking into a mom-and-pop agency for an auto quote and quickly advanced from receptionist to executive staff roles, driven by a passion for helping people understand the value of having the right coverage. They discuss how Florida’s market shifted from soft to hard due to fraud, insolvencies, carrier pullouts, and premium spikes, and how it’s now softening with more carriers returning and competing through offerings like leak detection technology to mitigate losses. Victoria explains why education and relationship-building can’t be replaced by online quoting or AI, how automation tools like Canopy Connect free time for coverage conversations, and lessons learned about adapting communication styles, avoiding rushed quoting, and building long-term referral-based client bonds.00:00 Why Coverage Matters00:41 Meet the Guest01:59 Accidental Insurance Career04:28 Passion for Education06:29 Market Shifts in Florida08:46 InsurTech Differentiators11:19 Automation Frees Advisors15:22 Choosing Value Over Price20:23 Why Humans Still Matter21:08 AI Job Fears22:22 InsurTech Reality Check23:21 Building Client Bonds26:20 Lessons From Failure29:20 Canopy Connect Pitch30:27 Meet Clients Where They Are33:58 Future Of Insurance36:27 Career Advice And Wrap38:09 Final Canopy Connect OutroConnect with Victoria: https://www.linkedin.com/in/victoria-ardito-1a2907133/

Meaghan Dowd on P&C Insurance Planning for Financial Advisors | Connected Conversations in InsuranceIn this episode of Connected Conversations in Insurance, host Ray Huang talks with Meaghan Dowd, Director of Insurance at Holistiplan, about why personal lines (P&C) insurance is a missing but high-demand piece of financial planning. Meaghan shares her background as a longtime insurance broker and explains how proactive insurance planning helps transfer risk, protect clients’ wealth, and support advisors’ fiduciary duty without requiring them to become insurance experts. They discuss market data showing low advisor adoption despite strong client interest, common friction between advisors and agents, and how needs-based reviews shift conversations away from price shopping. The episode also covers Holistiplan’s approach to education, the Canopy Connect integration to streamline declarations collection, and how automation may change quoting while increasing the value of contract and claims guidance.00:00 Why Insurance Matters00:37 Podcast Welcome01:53 About Meaghan Dowd 03:37 Holistiplan Growth05:58 Why Add PNC Planning07:53 Advisor Value of PNC10:14 Advisor Agent Collaboration14:05 Better Client Conversations17:41 Canopy Connect Ad Break18:47 Holistiplan Canopy Integration22:43 Industry Shift to Needs24:25 Building Advisor Referrals27:41 Canopy Connect Automation Ad28:47 Kiss Marry Kill Trends31:06 Future of Automation33:47 Wrap Up and Links35:07 Final Canopy Connect Outro

Tony Lew on InsurTechNY, AI, and the Human Side of Insurance | Connected ConversationsIn this episode of Connected Conversations in Insurance, host Ray Huang sits down with Tony Lew, co-founder and managing director of InsurTechNY, to discuss how the organization grew from filling a community gap in New York’s insurance innovation scene into a multi-pronged hub offering events, a corporate innovation membership program, an MGA-focused accelerator, and an early-stage venture fund. Tony breaks down how InsureTechNY helps carriers and brokers at different stages of innovation through education, market intelligence, and curated startup partnerships, and he previews the InsurTechNY conference’s content tracks, networking, expo expansion, and multiple pitch competitions. The conversation also explores how agencies can prioritize core systems like an AMS and CRM, automate back-office work, evaluate emerging AI tools, and differentiate in a rapidly changing landscape while keeping humans central to insurance.00:00 Why InsurTech NY Started00:41 Meet Tony Lew01:47 Four Pillars of the Hub04:18 Corporate Innovation Program06:14 Inside the Annual Conference08:06 Startup Competitions and Expo12:35 Global Reach and Attendees13:09 Sponsor Break Canopy Connect14:15 Agency Tech Differentiation20:47 AI Hype vs Real Use Cases24:45 Sponsor Break Automation Pitch25:49 Human Side of Insurance31:44 Hot Take AI Agencies Scaling34:11 Wrap Up and Where to Learn

Season 3 Kickoff: New Cohost, Podcast Mission, and Change in InsuranceSeason three kicks off with Ray sharing the updated vision for the show, exploring the people, stories, and technology shaping insurance and related industries.Ray also introduces new cohost Carrie Thornbrugh, Canopy Connect’s customer and partner marketing manager, who brings a background in marketing, community building, teaching, and even local radio.00:00 New Co-Host Tease00:44 Season Three Mission02:00 Meet Carrie Thornbrugh04:34 Show Format Explained05:42 Carrie's Origin Story07:36 From Teacher to Storyteller09:05 Collector Superpower12:04 Books and Slow Productivity16:51 Ray Superpower and Startup Roots22:43 Find a Way Culture23:29 Hot Topics Setup24:00 Agents Biggest Challenge24:39 Selling Change in Agencies27:14 Keep What Works Add Tech28:00 Hypergrowth and Change Fatigue29:27 Avoid the Tech Frankenstein30:55 Hot Seat Game Break32:25 Zombie Five Year Olds Debate36:21 Alternate Career Paths43:54 Season Three Wrap Up