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On the show
From 14 epsHost
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Recent episodes
Why AI in Insurance Isn’t Ready Yet | FrontRace’s Jack Siney
May 24, 2026
35m 30s
From Citadel Quant to Insurance CEO: How Arbol Is Rewiring Climate Risk Coverage
May 24, 2026
40m 18s
Surety Bonds Explained: The $Trillion Insurance Market No One Talks About | Gary Eastman
May 24, 2026
38m 13s
From Wearables to $100M+ Workers Comp MGA: How Kinetic Pivoted to Claims Oversight Software
May 24, 2026
56m 33s
AI Won’t Fix Insurance Until This Problem Is Solved with Luis Pino, ProducerFlow
Apr 24, 2026
37m 41s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 5/24/26 | ![]() Why AI in Insurance Isn’t Ready Yet | FrontRace’s Jack Siney✨ | AI in insuranceoperational inefficiencies+4 | Jack Siney | FrontRace | — | AIinsurance+5 | — | 35m 30s | |
| 5/24/26 | ![]() From Citadel Quant to Insurance CEO: How Arbol Is Rewiring Climate Risk Coverage✨ | climate risk coverageparametric insurance+5 | Sid Jha | ArbolCitadel+2 | — | insuranceclimate risk+7 | — | 40m 18s | |
| 5/24/26 | ![]() Surety Bonds Explained: The $Trillion Insurance Market No One Talks About | Gary Eastman✨ | surety bondsinsurance market+5 | Gary Eastman | SwiftBonds | — | surety bondsinsurance+7 | — | 38m 13s | |
| 5/24/26 | ![]() From Wearables to $100M+ Workers Comp MGA: How Kinetic Pivoted to Claims Oversight Software✨ | startup pivotworkers compensation+5 | Adam Price | Kinetic CompNationwide Mutual+1 | — | wearablesclaims oversight+6 | — | 56m 33s | |
| 4/24/26 | ![]() AI Won’t Fix Insurance Until This Problem Is Solved with Luis Pino, ProducerFlow✨ | insurance distributionproducer compliance+4 | Luis Pino | ProducerFlow | — | insuranceproducer onboarding+6 | — | 37m 41s | |
| 4/24/26 | ![]() The Future of Health Insurance Brokers in an AI World with Will Johnson CEO of Gyde✨ | health insuranceAI in insurance+4 | Will Johnson | GydeOscar Health | — | health insurance brokersAI platform+5 | — | 1m 13s | |
| 4/9/26 | ![]() OCR + LLM: The Architecture That Actually Scales AI in Insurance | Kasey Roh Upstage AI✨ | AI in insuranceOCR and LLM integration+5 | Kasey Roh | OCRLLM+2 | USinsurance+2 | AIOCR+6 | — | 48m 21s | |
| 4/8/26 | ![]() InsurTech Under Fire — Resilience, Insurtech, and the Future of Insurance with Kobi Bendelak✨ | resilience in insuranceIsraeli insurtech ecosystem+4 | Kobi Bendelak | InsurTech Israel | IsraelEgypt+2 | insurtechresilience+5 | — | 28m 35s | |
| 4/7/26 | ![]() Jame Benham, CEO of JKB and Terra: AI, Core Systems, and the Insurance Workforce Crisis✨ | AI in insuranceworkforce crisis+5 | James Benham | JKBTerra | insurance | AI adoptioninsurance workflows+5 | — | 43m 25s | |
| 4/6/26 | ![]() Why Wildfire Is Breaking Insurance (and How to Fix It) with Kitt Doucette, Co-Founder, W.I.S.H.✨ | wildfire riskinsurance pricing+4 | Kitt Doucette | Wildfire Insurance Solution HubW.I.S.H.+1 | — | wildfireinsurance+6 | — | 1h 09m 25s | |
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| 3/18/26 | ![]() How AI Is Becoming a Digital Teammate for Insurance Brokers | Anupam Gupta, CPO at Applied Systems✨ | AI in insurancebrokerage technology+4 | Anupam Gupta | Applied Systemsinsurtech+2 | — | AIinsurance+6 | — | 45m 52s | |
| 3/17/26 | ![]() Juan Garcia, Co-Founder of Tuio✨ | AIClaims Automation+5 | Juan Garcia | TuioAI+1 | SpainSouthern Europe | insuranceAI+8 | — | 43m 33s | |
| 3/1/26 | ![]() Josh Dorfman, co-founder and CMO of Plantd✨ | Climate TechConstruction Innovation+4 | Josh Dorfman | PlantedSpaceX | U.S.China+2 | climate techconstruction+6 | — | 40m 04s | |
| 3/1/26 | ![]() Katey Walker, Chief of Staff at Xceedance✨ | insurance operationsAI in underwriting+4 | Katey Walker | XceedanceU.S. FAIR Plan | — | insuranceoperations+7 | — | 36m 40s | |
| 2/28/26 | ![]() Sasha Haco, Founder & CEO of Unitary.ai | 🎙️ Episode 144 — AI, Automation, and the Real Work Behind Insurance OperationsIn Episode 144 of InsurTechTalk, I sat down with Sasha Haco, Founder & CEO of Unitary.ai, for a wide-ranging conversation that cuts through the AI hype in insurance.We explore why not every workflow needs AI, why deterministic automation still matters, and how the smartest teams are blending software, RPA, and AI reasoning—very deliberately. Sasha also breaks down the difference between AI as a feature and AI as the core product, and why large, multi-year “transformation projects” are quietly falling behind.From MGA submissions intake to underwriting operations, this episode is a practical guide to choosing the right tool for the job—not just the loudest buzzword.If you’re thinking seriously about AI, automation, and operational scale in insurance, this conversation is worth your time.#InsurTechTalk #AIinInsurance #InsuranceOperations #Automation #Underwriting #MGA #DigitalTransformation | — | ||||||
| 2/28/26 | ![]() Brian Greenbreg, CEO of Quoteplicity | 🎯 From SEO Gold Rush to AI-Driven Insurance FunnelsIn Episode 143, Gilad Shai sat down with Brian Greenberg to unpack one of the most complete real-world journeys in modern insurance distribution. The conversation traces Brian’s path from selling life insurance face-to-face at MetLife, to building and scaling a top-ranking life insurance website during the SEO “golden years,” exiting the operating business, and ultimately turning that hard-won technology into a platform now powering agents, agencies, RIAs, and financial professionals.The discussion highlights why life insurance is sold—not bought—and why funnels matter more than ever. Brian explains how nearly 90% of a life insurance application can be completed before an agent ever picks up the phone, and why direct-to-consumer life insurance models failed once the human layer was removed. We also explore how AI is finally helping agents tackle the hardest part of life insurance—underwriting—and why trust, consistent follow-up, and even physical mail continue to outperform purely digital strategies.This conversation is a masterclass in distribution strategy, funnel economics, and a clear reminder that the best technology in insurance doesn’t replace agents—it empowers them.If you’re in insurance, financial services, or InsurTech, this episode is worth your time.#InsurTechTalk #LifeInsurance #InsuranceAgents #AIinInsurance #DigitalDistribution #CustomerAcquisition #FounderStory #InsurTech | — | ||||||
| 12/11/25 | ![]() Lior Keren, President of Pumpkin | 🎙️ #insurtechtalk Episode 140 I sat down with Lior Keren of Pumpkin to explore the intersection of pet care and insurance.🐾 Pet insurance isn’t just about policies — it’s about trust at the vet’s office. 👉 The Vet Channel — where education, trust, and adoption really happen.This was a fun and fluffy conversation (pun intended 🐶🐱) with real insights for anyone building in the pet care ecosystem.Chapters:00:00 – Dog or Cat Person?02:45 – Emotional Value of Pets04:10 – Introducing Pumpkin06:00 – Pet Insurance vs. Wellness Coverage08:20 – How Pet Insurance Works10:50 – Market Size & Opportunity13:30 – Regulation & Innovation Barriers16:00 – The Vet Channel18:20 – Covered Pets & Product Scope19:30 – Why the U.S. Lags Behind21:30 – Behavioral Nudges & Awareness23:30 – Inflation & Pumpkin Now26:00 – COVID Surge & Pet Trends28:30 – Strategic Investors & Focus31:30 – Advice for Founders34:00 – Moving Fast in a Regulated Industry36:00 – Closing Thoughts & ITC Vegas | — | ||||||
| 12/11/25 | ![]() Stephanie Mier, Chief Insurance Officer at ServiceUp | 🎙️ On #InsurTechTalk Episode 141, Stephanie Mier, Chief Insurance Officer for ServiceUp, talks about modernizing Direct Repair Programs (DRP) in the insurance and auto repair industry. Discover how ServiceUp is leveraging technology, AI, and strong partnerships to streamline claims, reduce repair times, and create better outcomes for carriers, fleets, repair shops, and consumers. If you want to understand how digital innovation is reshaping insurance and auto repair, this episode is a must-watch!00:00 - Introduction & Welcome02:05 - Stephanie’s background in insurance and insurtech07:40 - What are Direct Repair Programs (DRPs)?12:20 - The legacy challenges in claims and repair networks17:30 - ServiceUp’s mission and value proposition23:10 - Role of automation and digital claims in modern insurance28:25 - Improving repair cycle times and efficiency34:55 - Collaboration with insurers, fleets & repair shops39:10 - Using AI for better claims experiences43:00 - The future of claims management & insurance technology46:00 - Final thoughts & recommendations47:30 - Closing remarks#InsurTechTalk #ServiceUp #DRPNetworks #DigitalClaims #InsuranceInnovation #ClaimsManagement #InsuranceTech | — | ||||||
| 12/10/25 | ![]() Stephanie Mier, Chief Insurance Officer at ServiceUp (clip 1) | 🎙️ On #InsurTechTalk Episode 141 (clip 1), Stephanie Mier, Chief Insurance Officer for ServiceUp, joined me to discuss ServiceUp and its game-changing partnership with Clearcover!She highlights why Clearcover is one of their most important partners:Tech & Scale: The technology is highly scalable! 📈 Clearcover played a key role in developing the insurance vertical at ServiceUp.Collaboration: They helped create new technologies, updates, and product additions specifically to simplify life for Clearcover's adjusters. A true industry collaboration! 🤝Dream Team: Stephanie gives a major shoutout to the fantastic Clearcover team, including Kyle, Aaron Wheaten, and Brandon (Senior Director of Damage), calling it the "greatest partnership ever".Seamless Workflow: Clearcover's entire adjuster team uses email to input data into the portal, ensuring instant visibility for all involved! 📧👀.#insurtechtalk #ServiceUp #Clearcover | — | ||||||
| 11/29/25 | ![]() Robert Lewis, CEO of INTX Insurance Software | From Dynamite to Reinsurance Tech: The Wild Origin Story Behind INTX Insurance Software.In this episode, we go on an unexpectedly fascinating journey — starting with coyotes and foxes, moving through African farming and UK wildlife, and ending in the heart of what this conversation is really about: insurance, reinsurance, and building modern core systems for carriers.Our guest, Robert Lewis, has one of the most unique backgrounds in the insurance world:🧨 8th-generation insurance lineageHis family first entered the industry because they *couldn’t get insurance* for transporting dynamite into South African mines — so they built their own mutual group, which ultimately grew into a Lloyd’s syndicate.🌍 From Mozambique to London to AustinRobert and his brother bought an insurance company in Mozambique 25 years ago. After struggling to find good software, they hired a young developer and built their own system, which eventually evolved into the modern platform that became Intx.💻 Rewriting over 1 million lines of codeIntx has since been rebuilt for the U.S. market on a Microsoft stack (SQL Server, C#, Blazor) to avoid proprietary coding traps and to make it easier to hire local developers without dependence on offshore or legacy languages.🧾 What Intx actually doesIn this episode, we dig deep into policy administration, reinsurance software, assumed/ceded reinsurance, treaty management, facultative placements, loss corridors, retrocession, regulatory reserves, claims integration, and why Excel remains the “core system” for 55% of insurance professionals.📉 Why legacy core systems are failingWe break down:* Why siloed systems (claims separate from underwriting) break the data chain* Why implementations cost carriers tens of millions* Why external integrators drag timelines for years* Why Intx is offering zero implementation cost and using its own insurance-literate team🏗 The new cohort of core system challengersWe discuss the Austin ecosystem (Guidewire → legacy, Duck Creek → aging guard, Socotra → modern competitor) and how Intx differentiates through its architecture, economics, and reinsurance depth.✔️ Family origins in South African insurance✔️ Building an 8-generation insurance legacy✔️ Starting an insurance carrier in Mozambique✔️ Building and modernizing core insurance software✔️ The difference between proprietary vs. Microsoft stack tech✔️ Reinsurance: ceded, assumed, treaties, facultative, loss corridors✔️ Retrocessions and capital markets✔️ Why Excel is still dominant in the industry✔️ Why most core system implementations never end✔️ The economics of modernizing a carrierIf you're an MGA, reinsurer, carrier, or investor in insurance infrastructure:This episode offers a rare, insider look at the technical, financial, and operational pain points within the core systems world—and how the next wave of challenger platforms is addressing them. | — | ||||||
| 10/6/25 | ![]() Dan Bratshpis, CEO of INSHUR #insurtechtalk #insurance #ondemanddelivery | 🎙️ #insurtechtalk, Episode 138 Dan Bratshpis, the CEO and co-founder of INSHUR, and Gilad Shai discuss INSHUR, the impact of the on-demand economy on the autonomous driving industry, and the new risks that the insurance industry needs to cover.Chapters:0:01 Introduction6:32 INSHUR11:53 Adapting to the market17:22 The future of autonomous vehicles and insurance24:00 Challenges in the TPA industry31:05 MGA and capacityhttps://www.linkedin.com/in/dan-bratshpis/https://inshur.com/en-us/ | — | ||||||
| 10/6/25 | ![]() Lior Keren, President of Pumpkin #petinsurance #insurtechtalk Data is King | 💡 Start small. Measure fast. Let data lead.🎙️ On #InsurTechTalk Episode 140 (clip 2), Lior Keren from Pumpkin explains why MGAs should pilot early and let real data—not assumptions—drive scale.“It’s easy to try to boil the ocean.Run a pilot, get real data fast. The real data is the king here.”📊 You can’t optimize what you haven’t validated.#InsurTech #MGA #DataDriven #InsuranceInnovation #PetInsurance | — | ||||||
| 8/14/25 | ![]() Chris Kalinski, CEO of Redkik | 🎙️ #insurtechtalk, Episode 137 (episode)Gilad Shai is hosting Chris Kalinski, CEO of Redkik. Redkik is an amazing global team that came together to re-envision cargo insurance. The team built and launched a high-performance per shipment cargo insurance offering that creates tremendous value add for our freight forwarder partners. Premiums are dynamic and custom for each shipment, provided in real time.https://www.linkedin.com/in/ckalinski/www.redkik.com | — | ||||||
| 7/31/25 | ![]() Dan Woods, CEO of Socotra | 🎙️ #insurtechtalk, Episode 136 (full episode)Dan Woods, CEO of Socotra, discusses the impact of AI on Insurance Core Systems, particularly on policy administration.Chapters:0:00 Tradition of the gong2:55 Team dynamics and sales culture6:12 Socotra8:50 The evolution of the policy administration systems11:30 The importance of data models in insurance14:35 Navigating regulatory challenges in insurance17:27 Innovation in product configuration20:19 Reflections on 11 years in insurance23:10 Limitations of legacy core systems25:15 Understanding software and its usability29:50 Remote work38:14 The future of AI in insurancehttps://www.socotra.comhttps://www.linkedin.com/in/danwoods1/ | — | ||||||
| 7/30/25 | ![]() Ali Safavi, CEO of COVU | 🎙️ #insurtechtalk, Episode 135 (episode)Ali Safavi, co-founder and CEO of COVU, joins Gilad Shai to talk about COVU, a customer management system for insurance agencies. https://www.linkedin.com/in/asafavi/https://www.covu.com/ | — | ||||||
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