AI Liability, Insurtech Innovation & The Future of Reinsurance | Freddie Scarratt (Gallagher Re) - Ep. 181

Freddie Scarratt, Global Deputy Head of InsurTech at Gallagher Re, joins James Benham and Rob Galbraith to unpack why 95% of all insurtech funding in Q1 2026 flowed into AI-focused companies, and what that means for the birth of an entirely new risk class: AI liability. From the Air Canada chatbot case that made headlines, to the hard lesson the industry learned when cheap venture capital tried to scale insurtechs like SaaS businesses, Freddie brings a reinsurance broker's view of where AI liability, cyber, and professional indemnity are converging into one digital risk category, and why insurance, unlike every other industry, can never fully cap its downside.

Cyber risk is evolving faster than the policies written to cover it. Rick Wong, Head of Insurance at Parametrix Insurance, sits down with James Benham live at RIMS 2026 to talk about the future of parametric cyber — and why the standard tech E&O form wasn't designed for the exposures that actually matter today. Parametrix is a Lloyd's coverholder writing parametric cyber, SLA, and enterprise risk. Named Cyber Underwriting Team of the Year at the Intelligent Insurer Awards, Q1 2026 already at 60% of full-year 2025 volume. In this episode:→ Why standard cyber policies fail data centers→ How parametric products are being used as financial tools — not just risk transfer→ AI-powered criminal organizations, nation-state actors, and what's coming in cyber threats→ Building a differentiated MGA in a space with growing capacity and real opportunity Guest: Rick Wong - Head of Insurance at Parametrix InsuranceWebsite: https://www.parametrixinsurance.com/LinkedIn: https://www.linkedin.com/in/rick-b-wong/ Host: James Benham - Founder & CEO at JBKnowledge Sponsor: Terra - Cloud-native Workers' Comp and P&C platform | terra.insure

Paul Andrews and Mark Elliott of PoloWorks join us to discuss how insurers can access,operate, and scale across the Lloyd’s and broader insurance market. Drawing on decades ofexperience across underwriting, reinsurance, and operations, they share how PoloWorks issimplifying complexity through turnkey managing agency solutions, outsourced services, andsupport across the full insurance lifecycle.

Danilo Raponi, Group Head of Innovation at Generali, joins us to discuss how one of the world’s largest insurers structures and scales innovation. From venture investments and startup partnerships to AI, IoT, and climate-focused solutions, Danilo shares how Generali is evolving insurance from a reactive claims payer to a proactive partner in risk prevention. 

Dr. Thomas Kuhnt, Chief Information Officer and Chief Operating Officer at HDI Global SE, joins hosts James Benham and Rob Galbraith to explore leading digital and AI transformation in corporate and specialty insurance — recorded live at Insurtech Insights London on March 18, 2026.Dr. Kuhnt's path is unlike most in insurance. A PhD in algebraic number theory from the University of Illinois Urbana-Champaign, 15 years at McKinsey building the European insurance practice, and now a dual CIO/COO seat overseeing technology, operations, and transformation at one of the world's oldest and largest industrial insurers. He brings a systems thinker's lens to one of the most complex transformation challenges in the industry.In this episode:• Why organizations must stop waiting for perfect conditions and start experimenting with AI now• How agentic AI is transforming input management and underwriting workflows at HDI Global• Why business leads — not IT — should own AI transformation in global insurance organizations• The process trap: how applying AI to broken workflows just accelerates the breaking• What the next 5–10 years really looks like for underwriters and claims professionals at the desk levelKey Quotes:"Don't wait. Start to experiment and iterate. This is not going to go away.""Business becomes IT — and IT becomes business.""We're overestimating the short-term impact — but underestimating it in the long term.""Seventy to eighty percent of an underwriter's work is just rekeying data. That's not really underwriting.""The first question should always be why — and that's an ops question, not a tech question."🔗 Connect:Dr. Thomas Kuhnt: https://www.linkedin.com/in/thomas-kuhnt/HDI Global SE: https://www.hdi.global/ | https://www.linkedin.com/company/hdi-global/👤 Hosts:James Benham: https://www.linkedin.com/in/jbenhamRob Galbraith: https://www.linkedin.com/in/rob-galbraith/🎙️ This episode is sponsored by Terra — the next-generation Workers' Comp and Commercial P&C Software.Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/📌 Find InsurTech Geek:LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/Twitter/X: https://twitter.com/InsurtechGeekInstagram: https://www.instagram.com/insurtechgeek/Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓

Amir Kabir, Founding & Managing Partner at Overlook Ventures, joins hosts James Benham and Rob Galbraith to reimagine risk in the age of AI — what the last decade of insurtech got wrong, where the next wave of opportunity actually lives, and why "liability is getting weird" is an understatement.Amir spent the first chapter of his career in Germany, building enterprise software at a Karlsruhe startup that was eventually acquired by a Silicon Valley company. In 2013 he immigrated to the US for an MBA at Georgetown, became the third person on the founding team at Munich Re Ventures, and helped grow that fund from $50M to over $1B. He later served as General Partner at AV8 Ventures leading the financial services practice before launching Overlook Ventures to invest full-time at the intersection of risk and frontier technology.In this episode:• Why the early insurtech era mistook insurance for a scalable SaaS business• "Insurance is a get-rich-slowly business" — and what that means for exit math• The Overlook thesis: investing in the infrastructure of risk across every tech cycle• Where AI is real in insurance today (claims, underwriting data extraction) — and where regulation still slows it down• The emerging risk categories that don't fit today's policy structures: autonomous systems, longevity, and reputational narrative riskKey Quotes:"Insurance is a get-rich-slowly business.""Technology moves in cycles. Risk always evolves through them.""Liability is getting weird.""Try to find a problem before you find a solution.""A brand can be destroyed in 48 hours by a viral moment."🔗 Connect:Amir Kabir: https://www.linkedin.com/in/amirkabir/Overlook Ventures: https://www.overlook.vc | https://www.linkedin.com/company/overlookvc/👤 Hosts:James Benham: https://www.linkedin.com/in/jbenhamRob Galbraith: https://www.linkedin.com/in/rob-galbraith/🎙️ This episode is sponsored by Terra — the next-generation Workers' Comp and Commercial P&C Software.Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/📌 Find InsurTech Geek:LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/Twitter/X: https://twitter.com/InsurtechGeekInstagram: https://www.instagram.com/insurtechgeek/Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓

Vineet Bansal, Chief Information and Technology Officer at The Mutual Group, joins hosts James Benham and Rob Galbraith to explore how technology leadership, disciplined AI adoption, and a shared operating model are shaping the future of mutual insurance — from inside a two-year-old, Bain Capital-backed startup built to help community-based carriers compete and grow.Vineet brings over 20 years of financial services and insurance technology experience to the role — from engineering roots in Nagpur, India, to nearly two decades at Fidelity Investments across ten different business lines, to building a greenfield digital platform as CTO at IptiQ by Swiss Re. Now at The Mutual Group, he's architecting a shared technology and operations platform designed to scale across multiple member companies — starting with GuideOne Insurance in Des Moines, Iowa.In this episode:Why insurance is a deliberately risk-managed industry — and what that means for responsible AI adoptionHow The Mutual Group is building a multi-tenant platform to help smaller mutual carriers access enterprise-level capabilitiesWhy clean data, API-driven ecosystems, and strong governance are the real foundation for AI success — not the tools themselvesWhat it means to hold the combined CIO and CTO role — and how Vineet divides his focus across operations, applications, strategy, and multi-member platformThe shift toward hyper-personalized insurance: policies sold by the hour, by the day, or only when the risk event is happeningKey Quotes:"The winners will be the ones with the strongest foundation.""Insurance sits at the intersection of risk, regulation, economics, and human behavior.""AI won't solve your data issues. It's garbage in, garbage out.""There's no easy answer. It takes meticulous planning and thoughtful execution.""We may have insurance products sold by the hour, by the day."🔗 Connect:Vineet Bansal: https://www.linkedin.com/in/vineet-bansal/The Mutual Group: https://www.themutualgroup.com/ | https://www.linkedin.com/company/the-mutual-group/👤 Hosts:James Benham: https://www.linkedin.com/in/jbenhamRob Galbraith: https://www.linkedin.com/in/rob-galbraith/🎙️ This episode is sponsored by Terra — the next-generation Workers' Comp and Commercial P&C Software.Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/📌 Find InsurTech Geek:LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/Twitter/X: https://twitter.com/InsurtechGeekInstagram: https://www.instagram.com/insurtechgeek/Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓

Holly O'Dell, President & CEO of Montana State Fund, joins host James Benham to discuss how systems thinking, people-first leadership, and strategic clarity are transforming workers' compensation — from inside a mission-driven organization that competes and wins in a fully open market. Holly brings a rare combination of credentials to the role: a BSN from Oregon Health & Science University, a JD from Lewis & Clark College, and an MBA from the Wharton School.Before joining Montana State Fund in 2022, she spent nearly 17 years at SAIF Corporation in Oregon, rising from trial attorney to VP of Strategy, Government Relations, Legal, and Procurement. Montana State Fund covers more than 60% of Montana's workers' comp market — in a fully competitive environment where they earn every dollar.In this episode:- Why risk tolerance is the real foundation of innovation — and how to build it before anything else- How Montana State Fund reduced 27,000 annual policy cancellations by two-thirds — without a single new technology- The people-first shift that brought claims turnover from 40% down to 4.5%- Building a culture where frontline employees have genuine FOMO about AI and innovation projects- What it means to be strategic in an industry full of shiny objects- The world's first workers' comp regulatory sandbox — and what it could unlockKey Quotes:"I'm not into norming. I'm into storming.""Risk is an opportunity for gain or for a loss.""Nonprofit is not a business model.""Strategy is an integrated set of choices.""This is an industry worth hanging out in."Timestamps:07:53 — The 20-sided dice: why insurance attracts multi-disciplinary thinkers15:12 — "I'm not into norming. I'm into storming." — Holly's leadership philosophy19:30 — Cancel cancellations: solving a 27,000-policy problem without technology23:57 — From 40% turnover to 4.5% — the people transformation at Montana State Fund27:04 — The FOMO effect: building a culture where everyone wants in on AI35:51 — Firefighter training injuries reduced from 50% to zero — the predict-and-prevent model in action🔗 Connect:Holly O'Dell: https://www.linkedin.com/in/holly-o-dell-26228452Montana State Fund: https://www.montanastatefund.com/ | https://www.linkedin.com/company/montana-state-fund/👤 Host:James Benham: https://www.linkedin.com/in/jbenham🎙️ This episode is sponsored by Terra — the next-generation claims and policy software for Workers' Comp.Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/📌 Find InsurTech Geek:LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/Twitter/X: https://twitter.com/InsurtechGeekInstagram: https://www.instagram.com/insurtechgeek/Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓

Dan Bratshpis, CEO and Co-founder of INSHUR, joins host Rob Galbraith to discuss how commercial auto insurance is being reimagined for the platform economy — and why traditional products are failing the drivers powering the gig economy.Dan built INSHUR from a two-person MGA startup into a 200-person global company operating across the US and UK, with embedded insurance partnerships with platforms like Uber, Amazon, and DoorDash. His approach: build coverage that works with how people actually live and work, not how insurers traditionally categorize risk.In this episode:Why traditional commercial auto products fall short for gig and platform workersHow INSHUR embeds insurance directly into platform onboarding — and what that data advantage means for underwritingThe usage-based wallet model: pay-per-ride, pay-per-delivery, pay-per-minuteHow COVID wiped out rideshare demand overnight — and became the pivot that launched INSHUR's delivery insuranceWhy INSHUR built Komodo Claims from scratch instead of outsourcing to TPAsWhat autonomous vehicles mean for frequency, severity, and the future of commercial auto insuranceKey Quotes:"What doesn't kill you makes you stronger.""Technology is an enabler to do things differently, do things better.""Claims is kind of at the heart of insurance.""These things don't get into accidents nearly as much as humans do." — on autonomous vehicles"Insurance is a really big part of protecting this new economy."Timestamps:09:05 — The wedding night pitch that launched Columbia Pacific Finance (placeholder — update with actual)10:55 — From Wall Street to rideshare insurance (placeholder — update with actual)19:13 — The COVID cliff: how INSHUR pivoted to delivery insurance overnight23:49 — Building Komodo Claims: why INSHUR owns its claims infrastructure26:22 — Autonomous vehicles and the frequency drop coming for commercial auto🔗 Connect: Dan Bratshpis: https://www.linkedin.com/in/dan-bratshpis/ INSHUR: https://inshur.com/ | https://www.linkedin.com/company/inshur/👥 Host: Rob Galbraith: https://www.linkedin.com/in/robgalbraith1/🎙️ This episode is sponsored by Terra — the next-generation claims and policy software for Workers' Comp. Visit 👉 https://terra.insure📲 Find InsurTech Geek: LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/ Twitter/X: https://twitter.com/InsurtechGeek Instagram: https://www.instagram.com/insurtechgeek/Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓

Hosts ⁠James Benham⁠ & ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Rob Galbraith are joined by Reghan Brandt, Chief Digital Operations Officer at K2 Insurance Services.Reghan joins us to discuss how digital strategy and operational transformation are changing the way underwriting teams, MGAs, and carriers work. With experience co-founding Columbia Pacific Finance and Loss Run Pro, Reghan shares a practical perspective on building scalable systems, driving technology adoption, and aligning people, process, and technology to create more efficient and human-centered insurance operations.This Episode is sponsored by ⁠⁠⁠⁠Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Twitter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠; or follow James on⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Twitter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!