InsurTechTalk

Jonathan Crystal opened Crystal Venture Partners on November 1, 2022. ChatGPT launched 30 days later. That timing tells you everything about where this conversation goes.In Episode 163 of InsurTechTalk, the third-generation insurance operator, former CFO of Crystal & Company, and Founder of Crystal Venture Partners joins me for a wide-ranging conversation on what he actually looks for in a founder, why he does not believe in InsurTech anymore, and what the industry is completely missing in its obsession with AI.In this episode:- Why Crystal Venture Partners is not an InsurTech fund — and why that distinction matters- The three things that make a business durable in an AI world: regulatory navigation, capital efficiency, and trusted relationships- How he backed Will Johnson at Gyde after eight to nine months of conversations before ever seeing a pitch deck- Why he skips the first six slides of every founder's deck — and what he actually wants to know instead- The death of pure SaaS: why outcome-based and gain-share models are replacing seat-based licensing- What venture capital actually means for a founder — and why it is the most expensive capital imaginable- How $150M+ in follow-on capital across 11 portfolio companies in six months validates the thesis- His answer to the closing question: the industry is talking too much about technology and not enough about people🔗 Learn more: https://www.crystalventurepartners.com/🔗 Connect with Jonathan: https://www.linkedin.com/in/jonathancrystal/InsurTechTalk is the podcast for insurance professionals, InsurTech founders, and anyone who wants a no-BS look at where the industry is headed.🔔 Subscribe for new episodes every week.

Everyone talks about the AI boom in terms of compute, models, and software. Justin Levine spends his days thinking about something different: who insures the actual construction of the data centers, energy assets, and projects that make all of it possible.The AI race moved from the cloud to the construction site. And the construction site has an insurance problem.In Episode 162 of InsurTechTalk, Shepherd Co-Founder & CEO Justin Levine — civil engineer turned construction risk manager turned InsurTech founder — explains how his company is building the first behavior-based commercial underwriting platform, why the Coalition-Allianz deal is a seminal moment for the MGU model, and how Shepherd Savings is rewarding contractors for technology they already use with up to 25% lower premiums.In this episode:- Why the construction insurance problem is speed and data, not capacity — and why that distinction matters- How Shepherd delivers underwriting indications in minutes by integrating with Procore, Autodesk, DroneDeploy, and OpenSpace- The personal auto telematics parallel: why commercial construction is 20 years behind on behavior-based pricing — and what happens when it catches up- Shepherd Savings: how rewarding existing technology adoption solves the change management problem that killed wearables in workers comp- Why data centers are actually a minority of Shepherd's $400B+ insured portfolio- The seven archetypes of data center construction — and why one size fits none of them- The Coalition-Allianz deal: the first proof point that technology-native MGUs can outperform legacy carrier underwriting- Closed-loop data center developments — power, compute, water, storage — and the new complexity they create for construction insurers- What is next for Shepherd: new programs, new verticals, and announcements expected in Q3🔗 Learn more about Shepherd: https://www.shepherdinsurance.com/🔗 Connect with Justin: https://www.linkedin.com/in/justindlevine29/InsurTechTalk is the podcast for insurance professionals, InsurTech founders, and anyone who wants a no-BS look at where the industry is headed.🔔 Subscribe for new episodes every week.

Cheri Martinen never planned to sell her family's insurance agency. Then she took a meeting that surprised her.In Episode 161 of InsurTechTalk, the fourth-generation agent and Managing Principal at OneDigital shares what made the difference — and drops one of the most practically urgent insights of the season: standard GL policies are now excluding AI-generated content, effective April 2026. Most business owners do not know. Many agents do not know either.In this episode:- Why she sold — and why it was a win for her employees, customers, and family, in that order- What made OneDigital different from every other approach she had received over the years- How to run an agency that sails through due diligence (hint: it is the same as running a good agency)- Why wildland firefighter contractors and water utilities became her niches — and why niche is a moat, not a limitation- The AMS filing cabinet problem that InsurTech still has not solved- Telematics, wildfire prevention, and the agent's role in risk education- The AI content liability gap: GL exclusions, cyber coverage gaps, and the new MGAs launching AI liability products to fill the void🔗 Connect with Cheri: https://www.cherimartinen.com/🔗 Learn more about OneDigital: https://www.onedigital.com/InsurTechTalk is the podcast for insurance professionals, InsurTech founders, and anyone who wants a no-BS look at where the industry is headed.🔔 Subscribe for new episodes every week.

Curtis Barton started ALKEME in the middle of COVID with seven agencies and $25 million in combined revenue. Five years later, it is a $350M+ brokerage operating in 35 states with over 85 acquisitions and backing from GCP Capital and Apollo S3.In Episode 160 of InsurTechTalk, Curtis breaks down the consolidation playbook in a way most people in the industry are not willing to say out loud — why most rollups are overleveraged, why organic growth is being faked through producer poaching, and why the brokerage model is being fundamentally rewritten by AI whether legacy players want it to or not.In this episode:1. The founding story: how Curtis convinced 6 P&C shops and a wealth management firm to build something together instead of selling out2. The integration playbook: signed bilateral roadmaps, day-one absolutes, and why disruption is the devil if you move too fast3. Why most consolidators are more leveraged than they report — PIK instruments, share class waterfalls, and the organic growth illusion4. AI governance at scale: how Alkeme built a BI team that deploys employee ideas the same day within a governed framework5. The prompt-based brokerage: querying the entire network like ChatGPT to find carriers, specialists, and introduction emails in seconds6. Why the AMS duopoly is more vulnerable than it looks7. Cybersecurity as a first-order M&A problem nobody talks about publicly8. The "NIL of the insurance producer world" — and why producer poaching is inflating organic growth numbers across the industry🔗 Learn more about Alkeme: https://www.alkeme.com/🔗 Connect with Curtis on LinkedInInsurTechTalk is the podcast for insurance professionals, InsurTech founders, and anyone who wants a no-BS look at where the industry is headed.🔔 Subscribe for new episodes every week.#insurtech , #insurancebrokerage, #mergersandacquisitions , #insurtechtalk , #insurance , #organicgrowth , #aiininsurance , #insuranceinnovation , #Alkeme, #privateequity , #InsuranceTechnology, #Consolidation, #InsurancePodcast, #Brokerage, #CurtisBarton

What if AI's role in insurance claims isn't to replace the adjuster — but to be a second set of eyes that never gets tired?Heather Wilson, CEO of CLARA Analytics, joins InsurTechTalk episode 159 to explain how her company's claims AI platform — trained on roughly 10 million claims over a decade — surrounds every workers comp, auto liability, and general liability case 24/7, looking for anything that could take it off course. The result: earlier detection of severity changes, better provider matching, litigation risk flags, and millions in reserving corrections that adjusters often miss simply because cases sit untouched for 90 days at a time.In this episode:• How CLARA's AI models learn from adjuster notes and documents — not just structured data fields (which are often filled out poorly)• The real story of a "finger cut" that escalated to an amputation, and how AI caught the severity shift before a human did• Why CLARA frames its AI as "augmented intelligence" — a safety net, not a replacement — and how that framing drives adoption• The change management playbook for getting senior adjusters to trust (and act on) AI alerts• How CLARA works across the entire insurance ecosystem — carriers from tier one to tier five, TPAs, self-insured corporates, and brokers who white-label CLARA's platform• Why "data orchestration" — not data ownership — is CLARA's real competitive moat• The hard truth about selling claims improvement: "we'll make you more profitable without increasing revenue" is one of the toughest pitches in insurance• Multi-tenant data contribution: how anonymized, aggregated industry data benefits every carrier on the platformHeather's vision for the future: connecting claims intelligence directly to actuarial and policy intelligence — closing the loop between the "left hand and right hand" of insuranceA grounded, practical look at what AI actually does inside a claims shop today — not hype, not science fiction, just better outcomes for claimants, carriers, and employers.🔗 Learn more about CLARA Analytics: https://www.claraanalytics.com/InsurTechTalk is the podcast for insurance professionals, InsurTech founders, and anyone who wants a no-BS look at where the industry is headed.🔔 Subscribe for new episodes every week.

AI is everywhere in insurance right now — but is the industry actually ready for it?In episode 157 of InsurTech Talk, Gilad Shai sits down with Jack Siney, co-founder and CRO of FrontRace, to discuss the gap between AI hype and operational reality.Jack explains why most insurance organizations still struggle with disconnected systems, weak data infrastructure, outdated workflows, and incomplete sales processes — and why simply “adding AI” will not solve those problems.The conversation explores:• Why today’s AI adoption resembles the AOL era of the internet• The hidden operational inefficiencies inside insurance organizations• Why most sales and distribution processes are poorly documented• The difference between automation and true operational intelligence• How AI can uncover why top producers outperform everyone else• Why insurers should focus on data readiness before buying more AI tools• The future of AI-driven sales management and underwriting workflowsA practical conversation for insurers, agencies, MGAs, founders, operators, and investors trying to separate real AI value from noise.Subscribe for more conversations with founders, carriers, brokers, investors, and operators shaping the future of insurance and insurtech.#InsurTech #Insurance #AI #ArtificialIntelligence #SalesTech #DigitalTransformation #InsuranceTechnology #EnterpriseAI #Innovation #Underwriting

What if insurance could pay out automatically — no adjuster, no claim dispute, no waiting?Sid Jha, CEO of Arbol, left a career trading commodities at Citadel to build exactly that. In Episode 158 of InsurTechTalk, Sid breaks down how Arbol went from a blockchain white paper in 2018 to a vertically integrated insurance platform spanning MGAs, a property carrier, and reinsurance — all purpose-built for climate-sensitive risks that legacy carriers are quietly retreating from.In this episode:- Parametric vs. traditional insurance — and why the old "basis risk" critique is stale- How Arbol underwrites climate risk using satellite data, AI, and quant methods- Why parametric is a bridge to alternative capital (hedge funds, tokenized funds, and beyond)- The vertical integration journey: MGA → MGU → carrier acquisition (Centuri, 2024)- Tokenized insurance risk — the original white paper vision that's finally becoming real- How Arbol approaches distribution in a market most brokers didn't know existed- The truth about climate risk: it's far more regionally varied than headlines suggestA rare conversation at the intersection of Wall Street, InsurTech, and climate — with someone who's been building quietly at that crossroads for nearly a decade.🔗 Learn more about Arbol: https://www.arbolmarket.com/🔗 Connect with Sid: https://www.linkedin.com/in/siddhartha-jha-ba4b7534/InsurTechTalk is the podcast for insurance professionals, InsurTech founders, and anyone who wants a no-BS look at where the industry is headed.🔔 Subscribe for new episodes every week.

Surety bonds are one of the least understood—but most critical—segments in the insurance ecosystem.In Episode 156 of InsurTech Talk, I sit down with Gary Eastman, founder of SwiftBonds, to break down how this “unsexy” category quietly supports trillions of dollars in economic activity—and why it’s becoming increasingly relevant again.Gary started as an attorney doing probate work, discovered court bonds, and turned a side project into an 18-year business focused entirely on surety. What followed is a masterclass in niche selection, distribution strategy, and underwriting discipline.We cover:What surety bonds actually are (and why they’re not traditional insurance)The three core categories: contract, court, and commercial bondsHow underwriting works in a “zero-loss assumption” modelWhy distribution—not product—is the real bottleneckThe evolution from referrals → SEO → AI-driven discoveryWhere AI can (and can’t) improve underwriting and operationsWhy specialization beats breadth in building a brokerageThe structural role of bonds in financing, construction, and legal systemsKey insight:Surety isn’t just a product—it’s infrastructure. It guarantees execution, compresses risk timelines, and keeps capital flowing in real-world projects.For founders, investors, and operators in insurance and fintech, this is a category hiding in plain sight.

What happens when your core product works perfectly — but your customers still don't stick around?Adam Price, CEO of Kinetic Comp, joins InsurTechTalk episode 155 to unpack one of the most honest startup pivot stories in InsurTech: how Kinetic went from a wearable device company to a $100M+ workers comp MGA powered by claims oversight software — and why that shift was driven entirely by listening to policyholders and brokers.In this episode:Why wearables work great — but change management kills adoptionThe real reason prevention tech struggles in mid-market workers' compHow Kinetic transitioned from hardware to a software-based claims oversight platformWhat "data fusion" actually means in practice (not just buzzwords)The Nationwide Mutual partnership and what a full-stack carrier relationship really looks likeHow to pitch an MGA to investors — and why the $6 trillion TAM slide won't cut itAI in insurance: Kinetic's honest "5 or 6 out of 10" self-assessmentTips for InsurTech founders building MGAs from scratchWhether you're building in workers comp, launching an MGA, or trying to figure out where prevention tech fits in your product strategy — this one is packed with hard-won lessons.🔗 Learn more about Kinetic: https://kineticcomp.com/

Most insurance leaders focus on distribution, underwriting, or AI.But there’s a quieter constraint slowing everything down: producer compliance and onboarding.In episode 154 of InsurTechTalk, Gilad Shai sits down with Luis Pino, CEO of ProducerFlow, to unpack the infrastructure layer behind insurance distribution—how carriers, MGAs, and agencies actually get producers licensed, appointed, and ready to sell.We go deep on:Why producer onboarding speed directly impacts revenueThe hidden complexity behind licenses, appointments, and compliance workflowsHow poor onboarding creates drop-off before production even startsWhy data quality—not AI—is still the limiting factorThe different risk tolerance between carriers and agencies when adopting AIWhere the real moat is forming: data, workflows, and liability ownershipProducerFlow sits at the intersection of compliance, data, and distribution—turning what’s traditionally a back-office function into a frontline growth driver.If you’re a carrier, MGA, agency, or investor, this is a conversation about the layer of insurance most people ignore—and why that’s where leverage is shifting.

In Episode 153 of InsurtechTalk, Gilad Shai sits down with Will Johnson, CEO and Co-Founder of Gyde, to unpack one of the most overlooked—and misunderstood—segments in insurance: health insurance distribution.This conversation goes beyond the AI hype cycle. It dives into the real bottleneck in insurance: the broker.Will shares how Gyde is building an AI-powered platform designed to help agency owners break through capacity constraints, automate low-value workflows, and return to what actually matters—advising clients and growing their business. From renewal automation to client service and cross-selling, this is a deep look into what a true “broker operating system” looks like in health insurance.We also explore:Why health insurance is fundamentally different from P&C—and harder to fixThe growing pressure on brokers, carriers, and the entire systemHow AI is actually being used (and where it’s not)Why distribution is regaining power after years of disintermediation narrativesThe shift from “selling policies” to becoming a true strategic advisorWill brings a rare perspective shaped by nearly a decade at Oscar Health, where he saw firsthand how critical brokers are—and how underinvested they’ve been.Key takeaway:AI won’t replace brokers. But brokers who use AI will replace those who don’t.

Episode 152 of InsurTechTalk Kasey Roh--Head of US, Upstage AI: Building the “Perfect Marriage” Between OCR and LLMs.What happens when AI stops trying to boil the ocean—and instead solves one of the most painful, expensive problems in enterprise workflows?In this episode, I sit down with Kasey Roh, Head of US at Upstage AI, to unpack how a focused, infrastructure-first approach to AI is quietly transforming industries like insurance, healthcare, and manufacturing.We start somewhere unexpected—yoga, discipline, and managing chaos in the age of AI—and quickly move into one of the most important conversations in enterprise tech today: why most AI implementations fail to scale, and what it actually takes to build systems that compound.Upstage isn’t just another “AI wrapper.” They’ve built both their own OCR engine and a proprietary LLM (SOLAR), designed specifically for document understanding—arguably one of the most overlooked bottlenecks in enterprise operations.Key topics we cover:1. Why traditional OCR only solves ~10–20% of enterprise document workflows2. The hidden cost problem of LLMs at scale (tokens, GPUs, inference)3. Why hallucinations kill enterprise trust—and how to design around them4. The “OCR + LLM” architecture as a pragmatic middle ground5. Turning 10 years of unused documents into entirely new insurance products6. Why AI in enterprises is not about automation—but accountability7. The real test for AI adoption: does your investment *compound*?We also go deep on:1. Evaluating AI vendors in a world full of “AI-washing”2. The importance of owning core models vs. relying on wrappers3. Human-in-the-loop systems as a feature—not a limitation4. The future of agentic workflows and governanceThis is a must-watch for operators, investors, and anyone trying to separate signal from noise in the AI hype cycle.Timestamps:00:00 – Yoga, chaos, and entering the AI world04:30 – What Upstage actually does (OCR + proprietary LLM)12:00 – Why enterprise OCR is fundamentally broken20:10 – The cost vs. accuracy tradeoff in LLMs28:45 – Unlocking value from “dead” enterprise data38:20 – AI vs. humans: accountability and trust47:10 – Evaluating AI vendors (what actually matters)55:00 – The compounding framework for AI investmentsAbout Kasey Roh:Formerly at Tesla and Meta, Kasey transitioned from corporate finance and venture investing into operating, now leading Upstage’s US expansion. Upstage has raised ~$150M and is scaling rapidly across global enterprise markets.

InsurTech Under Fire — Resilience, Insurtech, and the Future of Insurance with Kobi BendelakWhat does resilience actually look like?In this episode, we sit down with Kobi Bendelak, who shares an unbelievable story: leading a delegation of 20 startups and 40 people out of Israel during wartime—when all flights were canceled.The solution?A 40-hour journey through the desert, crossing into Egypt, flying via Athens, and pushing forward to London.Not for optics. For trust.Because in insurance, showing up isn’t optional.What we cover in this episode:* The “reverse exodus” journey from Israel via Egypt to London under fire* Why trust is the foundation of the insurance industry* How the Israeli insurtech ecosystem continues to grow—even during a crisis* The evolution of insurtech: from “tech tourism” to real business outcomes* Why B2C insurtech startups had to rethink distribution (hint: brokers win)* The rise of global collaboration across ecosystems* A bold prediction: AI could replace core insurance systems sooner than expectedChapters:00:00 – Introduction02:10 – The 40-hour journey to London08:45 – Resilience and trust in insurance15:20 – Growth of the Israeli insurtech ecosystem24:30 – From “tech tourism” to real business32:10 – B2C vs brokers: hard lessons41:50 – Global expansion and new markets49:30 – AI and the future of insurance core systemsAbout InsurTech IsraelInsurTech Israel supports over 250 startups through investments, accelerators, global roadshows, and partnerships—making it one of the most active insurtech ecosystems in the world.Key takeaway:Resilience isn’t a story you tell.It’s what you do when everything works against you—and you show up anyway.👍 Like, comment, and subscribe for more conversations with leaders shaping the future of insurance and technology.#Insurtech #AI #Insurance #Startups #Innovation #Leadership

What happens when AI doesn’t just support insurance workflows—but replaces them?In Episode 150 of InsurTechTalk, James Benham breaks down what’s really happening inside insurance companies right now:Why ~30% of the workforce is stuck in manual clerical workThe growing shortage of underwriters and adjustersHow AI is reshaping core systems, workflows, and decision-makingWhy most “AI adoption” today is risky, untested, and non-compliantAnd what it actually takes to build a modern, AI-native insurance stackFrom rebuilding policy and claims systems to embedding AI directly into workflows, this conversation goes beyond hype—and into execution.If you want to understand where insurance is really headed, start here.

Episode 149 — InsurtechTalk | Kitt Doucette (Co-Founder, Wildfire Insurance Solution Hub)Wildfire risk is no longer just a catastrophe event—it’s a systemic failure in how insurance understands, prices, and communicates risk.In this episode, Kitt Doucette breaks down why wildfire conflagration is fundamentally different from traditional fire risk—and why the insurance industry must treat it as its own standalone peril.From his background as a professional skier and journalist embedded with wildfire response teams, to building a next-generation insurance platform, Kitt brings a unique perspective on risk, resilience, and prevention.What we cover:• Why wildfire “conflagration” is a distinct and misunderstood risk• The failure of the current reactive insurance model• How FAIR Plans are distorting the market• Why insurers rely on models—but use them the wrong way• The core challenge of pricing prevention vs. reacting to loss• How technology can quantify mitigation (before vs. after risk)• The role of communities, HOAs, and homeowners in risk reduction• Why insurers should act as both incentivizer and enforcer• The case for separating wildfire as a single, insurable peril• WISH: building transparency between insurers and homeownersKitt also outlines how Wildfire Insurance Solution Hub (WISH) is creating:Parcel-level risk visibilityActionable mitigation strategiesA direct link between risk reduction and insurance pricingKey takeaway:Wildfire risk is increasingly manageable—but only if the industry shifts from reactive underwriting to proactive risk engineering.🎙 InsurtechTalk — conversations with founders, CEOs, investors, and operators shaping the future of insurance.Wildfire Insurance Solution HUBhttps://www.linkedin.com/company/wish-wildfire-insurance-solution-hub/

AI is everywhere in insurance conversations—but what does it actually change inside a brokerage?In Episode 148, I sit down with Anupam Gupta, Chief Product Officer at Applied Systems, one of the largest insurtech platforms serving insurance agencies and brokers worldwide.We discuss how the agency management system (AMS) is evolving from a simple system of record into a system of action—powered by AI and digital teammates that help brokers get work done faster.Some of the topics we cover:• Why most commercial insurance submissions still happen through email• How AI agents can prepare renewal packets automatically• Why brokers remain essential as trusted advisors even in an AI-driven world• How automation can reduce administrative work and free brokers to focus on clients• The challenge of change management as agencies adopt new technology• Why the future brokerage will include human experts supported by digital teammatesWe also discuss Applied Systems’ role in the industry, how insurtech competition is evolving, and what brokers should expect from the next generation of insurance technology.Key takeaway:AI won’t replace brokers—but it will dramatically change how work gets done behind the scenes.If you work in insurance, brokerage technology, or insurtech, this conversation provides a practical look at where the industry is heading.

InsurTechTalk Episode 147AI, Claims Automation, and the Future of Insurance | Juan (Tuio) on Building an AI-Native InsurerIn this episode of InsurTechTalk, we sit down with Juan, co-founder of Tuio, a fast-growing Spanish insurtech that is rethinking personal insurance using AI, automation, and behavioral data.Tuio launched in 2021 to serve a segment that traditional insurers struggle with: digitally native customers who expect self-service insurance, transparent pricing, and fast claims resolution. Instead of building another digital wrapper around legacy systems, Tuio designed a platform that uses AI agents to optimize the two biggest drivers of insurance profitability: marketing and claims.Juan explains how their AI system—nicknamed “Watson”—analyzes massive claims datasets, reviews videos and documents submitted by customers, and recommends the next best action for adjusters. Rather than replacing humans, the system creates a human-in-the-loop model where adjusters supervise AI decisions and focus on the most valuable part of the job: helping customers.We also discuss:• Why most AI projects in insurance focus on the wrong cost centers• How Tuio uses AI to improve underwriting, marketing efficiency, and claims handling• Why automation alone doesn’t improve profitability• How digital self-service generates richer underwriting data• The regulatory challenges of AI in insurance pricing• The opportunities for insurtech startups across Spain and Southern EuropeTuio currently serves 100,000+ customers, writes €15M in premiums, and is growing 10% month-over-month following a €15M Series A round led by MassMutual Ventures.If you want to understand how AI is moving from pilot projects to real P&L impact in insurance, this conversation is for you.Guest: Juan Garcia — Co-Founder, TuioHost: Gilad ShaiSubscribe for more conversations with founders, investors, and operators shaping the future of insurance, insurtech, and financial infrastructure.#Insurtech #AI #InsuranceInnovation #Startups #ClaimsAutomation #Fintech

Episode 146 | Climate Tech, Construction Innovation & Insurance RiskWhat does climate tech have to do with construction and insurance?In the first InsureTech Talk episode of 2026, I sit down with Josh Dorfman — climate entrepreneur and Founder of Planted — to unpack the intersection of climate innovation, supply chain resilience, advanced manufacturing, and insurability.Josh shares:- How Planted grows a structural biomass 10x faster than trees- Why verticalized supply chains matter for homebuilders- The real impact of energy competition between the U.S. and China- What $2 trillion per year in clean energy investment actually means- How better building materials could change the insurance equation- Why resilience is the missing link between climate and insurabilityWe also discuss:Fire, hurricanes, and why insurers are pulling back in CA & FLCarbon removal vs. practical climate solutionsAdvanced manufacturing, SpaceX DNA, and scaling hard techWhy construction innovation is becoming an insurance storyIf you care about the future of housing, underwriting, climate resilience, and where capital is flowing next — this episode is for you.Listen now.#InsurTech #ClimateTech #Insurance #ConstructionTech #Resilience #Energy #Underwriting #VentureCapital

🎙️ InsurTechTalk, Episode 145 | Inside the Operating Layer of Insurance with XceedanceIn this episode, I sit down with Katey Walker, Chief of Staff at Xceedance, to unpack the part of insurance most people misunderstand—and underestimate: operations.We discuss why Xceedance doesn’t sell insurance or deploy capital, how vertical domain expertise combined with AI is reshaping underwriting, claims, and actuarial work, and what it really takes to modernize insurance infrastructure globally.From standing up a U.S. FAIR Plan in 120 days to scaling a 5,500-person global services platform, this conversation is a masterclass in how insurance actually runs—and where it’s going next.

🎙️ 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

🎯 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

🎙️ #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

🎙️ 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

🎙️ 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

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.

🎙️ #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/

💡 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

🎙️ #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

🎙️ #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/

🎙️ #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/

🎙️ #insurtechtalk, Episode 134 (episode)Laura McDonald and Dr. Christy Lane, co-founders of Flora Fertility, talk with Gilad Shai about Flora Fertility, fertility Insurance, and the iceberg of fertility challenges modern life has bestowed on us.https://www.heyflora.co/abouthttps://www.linkedin.com/company/heyflora/https://www.linkedin.com/in/laurajaynemcdonald/https://www.linkedin.com/in/christyclane/

🎙️ #insurtechtalk, Episode 133 (episode)https://www.linkedin.com/in/maheshvinayagam/http://www.qbotica.comChapters:0:05 The rise of Pickleball: a social phenomenon 4:24: qBotica9:12 Automation as a Service14:10 Agentic AI: The future of automation19:20 Navigating the insurance industry21:49 The entrepreneurial leap24:40 Lessons learned: overcoming adversity

🎙️ #insurtechtalk, Episode 132 (episode)Fred Blumer joined Gilad Shai on the #insurtechtalk podcast to talk about Mile Auto, insurance pay-per-mile, and collaboration with Porsche.https://www.mileauto.com/https://www.linkedin.com/in/fredblumer/

🎙️ hashtag#InsurTechTalk, Episode 131 (full episode) Adam Chadroff about the Insurance Capital Summit that the Equal Ventures team produces in NYC on May 8th. For more details and to request an invite, check out https://www.ics.equal.vc/

🎙️ #InsurTechTalk, Episode 130 (episode)Benefit Bay empowers the brokers to differentiate or die.Brandy Burch, the CEO of Benefit Bay, discusses how Benefit Bay empowers benefit brokers to differentiate themselves from the competition.https://www.linkedin.com/in/brandy-burch-24389536/http://www.benefitbay.comChapters:0:05 Introduction and background2:10 The Benefits of the ecosystem5:15 Empowering Choice8:06 Building trust: The role of brokers and employers10:17 Benefit Bay: from concept to reality12:43: Brandy: The journey to benefits and FinTech15:55 The Future of Benefit Bay23:00 Navigating the complex benefits landscape26:27 Benefits as a player in the talent acquisition race28:00 The challenges faced by the brokers37:17 The heart of Benefit Bay: A passion for solutions 42:00 Learning from early mistakes50:00 Defining success beyond signups

🎙️ #InsurTechTalk, Episode 129Lisen Kaci, CEO of Discrepancy AI, discusses AI Tool Chaining and how they developed and linked together different models to reach better results.https://www.linkedin.com/in/lisen-kaci/https://www.discrepancyai.com/Chapters:0:05 Microelectronics and autodidact 03:07 Innovation with AI - the birth of Discrepancy AI06:12 Navigating challenges in the LegalTech space08:59 Revolutionize reports in the Insurance sector11:51 Data security and the client's trust17:39 AI Tool Chaining and Model Selection20:28 Learning from failures24:01 Growth plans

🎙️ #InsurTechTalk, Episode 128 (episode)Elan Nyer, CEO and co-founder of Ownli joined Gilad Shai to talk about data ownership and meaningful data in the insurance industry.Chapters:00:45 Introduction to Ownli - a new data ownership paradigm01:50 The concept of data ownership and compensation07:15 Elan's background09:25 The Value of meaningful data in insurance12:04 Engagement strategies with insurance companies 14:34 Aha moment16:22 Beyond insurance 22:57 What's next?25:45 The capitalhttps://www.linkedin.com/in/elan-nyer-a4691823/https://www.ownli.co/businesses/acquire/insurance

🎙️ #InsurTechTalk, Episode 127Brad Schneider, CEO of Nomad Data, talks about asking users for feedback as a secret sauce for improving AI and data categorization.https://www.linkedin.com/in/bradschneider/http://www.nomad-data.comChapters:3:45 Exploring the world of data6:35 Innovation in data and AI8:00 Understanding Nomad Data's unique approach 16:30 Insights from ITC and other conferences19:40 Challenges and Successes in business growth21:05 The future of data and automation

🎙️ #InsurTechTalk, Episode 126 Todd Greenbaum, CEO of Input 1, discusses Input 1, premium financing, payments, and billing systems.https://www.linkedin.com/in/todd-greenbaum-7161b0a2/https://www.input1.com#insurance #paymentsystems #billingsolutions

🎙️ #InsurTechTalk, Episode 125 (episode)Kabir Syed and Gilad Shai discuss Kabir's latest company ennabl. ennabl provides a data platform to insurance agents and brokers, or in other words - truth and understanding of what's going on with the risk (insured) that the agent is trying to place (shop of an insurance policy from one of the many insurance companies).Chapters:0:10 Tbilisi3:20 Kabir Syed's entrepreneurial journey10:52 Enabling insurance brokers17:54 Automation and data quality24:56 Challenges and quirks of the insurance industry31:25 The need for automation and digitalization in the insurance industry37:36 Focusing on solving problems42:27 Company valuations and M&A in insurance. Let's meet at ITC.

🎙️ #InsurTechTalk, Episode 124.Bill Harris and Drake Slaikeu-Lawhead join Gilad Shai to discuss behind-the-scenes topics, such as what's with the astronauts. How can you still grow? How do you boldly go where no insurer has gone before? The "solar system" of InsureTech Connect and the gravitational forces that are at work to allow "moons" to orbit "planets."🤝 Sign up for my town-square meet-up about "Exit and M&A in Insurance: Valuation for Startups and Agencies." https://lu.ma/2n7nr4hi🎟 Join us at ITC Vegas. ⁠https://i.snoball.it/p/Epak/fm⁠🌟 Special Offer: Save an additional $200 off with code: ITCV24SPSNOEB or 200ITC701https://www.linkedin.com/in/billharris3ubiq/https://www.linkedin.com/in/drake-slaikeu-lawhead-54327815/

🎙️ #InsurTechTalk, Episode 124 (clip 2) There are more than 60 parties (that we know of), wine tastings, and meet-ups during the week of InsureTech Connect. 🤝 Sign up for my town-square meet-up about "Exit and M&A in Insurance: Valuation for Startups and Agencies." https://lu.ma/2n7nr4hi 🎟 Join us at ITC Vegas. ⁠https://i.snoball.it/p/Epak/fm⁠ 🌟 Special Offer: Save an additional $200 off with code: ITCV24SPSNOEB, or 200ITC701Enjoy!

🎙️ #InsurTechTalk, Episode 124 (clip 1) I chatted with Bill Harris and Drake Slaikeu-Lawhead about ITC. We touched on many behind-the-scenes topics, such as what's with the astronauts. How can you still grow? How do you boldly go where, hmmm, gone before? The "solar system" of InsureTech Connect and the gravitational forces that are at work to allow "moons" to orbit "planets." 🎟 Join us at ITC Vegas. https://i.snoball.it/p/Epak/fm 🌟 Special Offer: Save an additional $200 off with code: ITCV24SPSNOEB, or 200ITC701Enjoy!

🎙️ #InsurTechTalk, Episode 123 (episode) Marty Smuin, CEO of ARTURO.ai, and Gilad Shai discuss ARTURO, the data and clarity from geospatial resources, and a fresh approach to customers. Chapters: 0:10 Introduction 1:40 Marty's Background 7:28 What is Arturo? 10:23 Differentiating Factors of Arturo in the Geospatial Insights Market 14:20 Addressing Policyholders and Providing Actionable Insights 18:57 Who is the Customer? 19:21 Adoption of New Technology by Insurance Carriers 23:03 Challenges and Feedback in the Insurance Industry 26:25 Differentiation between Top Tier and Regional Carriers 32:22 Advice for New Entrants to the Insurance Industry 35:00 InsureTech Connect (ITC) 2024. Come and meet us at our booth.

🎙️ #InsurTechTalk, Episode 123 (clip) Marty Smuin, CEO of Arturo, shares his thoughts on geospatial imagery and the value it provides to the insurance industry. https://www.arturo.ai/ https://www.linkedin.com/in/marty-smuin-33941b1/

🎙️ #InsurTechTalk, Episode 122 (episode) Bruce Broussard, Managing Director at Percipience, joins Gilad Shai to discuss insurance data, Percipience's data platform, LSU, and football (soccer). Chapters: 0:00 Let's talk about the Euro Cup and Copa América 3:16 Introduction Bruce and Percipience 6:32 What is the challenge of insurance data? 10:13 The role of data in underwriting and claims 13:09 Models and Regulation 17:30 Data and decision making. How do we help the CxO? 20:47 ML, algorithms, and documenting for regulators 23:16 The challenge that the Core System providers face 28:06 Decision-making by the regional carriers 39:54 Finding the data provider gems at ITC's expo hall 45:05 What would you advise your past self just entering the insurance industry? https://www.linkedin.com/in/bruce-f-broussard-jr-flmi-acs-59481b/ https://percipience.com/

🎙️ #InsurTechTalk, Episode 121 (full episode) Many are familiar with the quality, time, and cost project-management triangle. In their conversation, Gilad Shai and Jon Corrin, co-founder and CEO of XILO.io, talk about the trade-off between product, sales, and customer success. Chapters: 0:00 The SoCal lifestyle and XILO 3:17 The role of automation in the insurance industry 6:05 The Agents' Customer experience 13:15 XILO's customers 15:38 Second Startup 21:31 Applying knowledge from software development to insurance 25:43 Trade off between Sales - Product - Customer Experience 38:10 Advice https://www.xilo.io/ https://www.linkedin.com/in/jonathancorrin/

🎙️ #InsurTechTalk, Episode 121 (clip) Jon Corrin, co-founder and CEO of Xilo.io, presents XILO.io and the value it provides their clients by automating workflows. https://www.xilo.io/ https://www.linkedin.com/in/jonathancorrin/

🎙️ #InsurTechTalk, Episode 121 (clip) Jon Corrin, co-founder and CEO of Xilo.io, shares advice for startup founders who enter the insurance and financial industries. https://www.xilo.io/ https://www.linkedin.com/in/jonathancorrin/

🎙️ #InsurTechTalk, Episode 120 (episode) Jared Brier, co-CEO and founder of AKKO joined Gilad Shai to discuss AKKO, Customer and User Experience, Warranty, and BMW Z4. Chapters: 0:05 Driving 4:01 Introduction 9:08 Warranty 12:00 Customer Experience 28:54 Memorabilia 29:56 Advice