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InsurTech Geek Podcast: Daily Summaries Delivered
by JBKnowledge
A bi-weekly interview series highlighting the technology that is shaping the future of insurance and exploring how industry leaders are leveraging technology to grow their businesses.
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- 2 weeks ago23 min
From AI Activity to Real Impact with Jay Bell from Zurich North America.
Jay Bell, COO and Head of Business Transformation, Global Construction and Surety at Zurich North America, joins host James Benham live at ITC 2026 to explore AI, insurance transformation, and how to turn technology into measurable impact.Jay served six years as an enlisted Marine, then worked as one of the first DSL installers in the country before starting over at 29 as a workers' comp claims adjuster at The Hartford. He became a team leader in about 18 months, traded his Six Sigma skills for an underwriting education, chose construction as the closest he could stay to a blue collar role within a white collar world, and went on to lead The Hartford's middle and large commercial programs before joining Zurich North America. He is also the author of The Goat in the Machine, a leadership field guide to turning AI activity into measurable impact.In this episode:→ Why so much AI work measures activity instead of impact, and why every rollout needs a baseline before it starts.→ Why the industry keeps pointing efficiency efforts at the same intake problems and still expects a different return.→ How Zurich's DAILY (Driving AI Literacy) group grew with no mandate and no budget, and turned casual users into citizen builders.→ How to keep Lean and Six Sigma discipline while hiding the method from underwriters, and why operations should hire people who have done the underwriting job.→ Seven goats, three sheep, and the story behind The Goat in the Machine and its free nine question team assessment.Key Quotes:"I've started to get more relentlessly focused on the difference between activity and impact.""We're just continuing to do the same things we've always been doing.""It's all about empowering the people.""We're turning regular folks into real citizen builders."Chapters:00:00 Cold open00:26 AI activity versus real impact, live at ITC 202601:36 Las Vegas, construction and surety03:10 Connecticut roots and the Marine Corps04:14 Marine assaultman, 1993 to 199905:11 From the phone company to work comp claims at 2906:22 Team leader at 18 months and the Six Sigma trade into underwriting07:42 Choosing construction: a blue collar role in a white collar world08:07 Walking a mile in underwriting's shoes10:32 Claims transformation without claims chaos10:59 Not a technologist: empowering the individual12:06 Activity versus impact: what can people do now?12:45 Lean, 2 Second Lean and Six Sigma behind the scenes14:57 AI, the multi-tool15:29 DAILY: AI literacy with no mandate and no money16:03 How a casual user became a citizen builder17:03 Copilot, Cowork and the frontier models18:34 The Goat in the Machine19:11 Goats, sheep and leading with your weirdness20:25 A field guide and a nine question team assessment21:23 Goats clearing land22:41 Where to get the book, and wrap up🔗 Connect:Jay Bell: https://www.linkedin.com/in/jaybbell/Zurich North America: https://www.zurichna.com | https://www.linkedin.com/company/zurich-north-america/The Goat in the Machine (free copy): https://goatinthemachine.net👤 Host:James Benham: https://www.linkedin.com/in/jbenham🎙️ 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! 🤓
- Oct 9, 202633 min
Cyber Risk Engineering and Emerging AI Risks with Jay Vinda from Mosaic Insurance
Jay Vinda, Global CISO and Cyber Risk Engineering Lead at Mosaic Insurance, joins host James Benham live at ITC 2026 to explore cyber risk engineering, the emerging risks surrounding AI, and how cybersecurity intelligence is changing insurance.Jay grew up in London wanting to be a chef, studied mechanical engineering, and spent a couple of months in Peru building wind turbines for villages without electricity. A cybersecurity graduate scheme in 2016 was meant to last a couple of years; he stayed, earned a master's in information security while working, and spent about eight years protecting banks and government before moving into insurance. At Mosaic he protects the company as its CISO and helps its cyber underwriters assess every risk the way an attacker would.In this episode:• Why the person who buys a cyber policy and the CISO who knows what could go wrong are rarely in the same conversation, and how Jay bridges the two.• How criminal marketplaces and ransomware operators made funding, not technical skill, the real barrier to cybercrime.• Why generative AI erased the old phishing tells, and what the scams that work today look like: no urgency and no link.• Why the basics still beat the shiny tools, and why so much "AI-powered" security is fluff.• What frontier AI changes for defenders, from vulnerabilities that sat undetected for 26 years to a risk appetite far lower than a criminal's.Key Quotes:"Insurers have loads of data, but they're just not using it very well.""Social engineering is still a very easy way to compromise a company.""Our risk appetite on the defensive side is just a lot lower than a criminal's.""Really, you don't need that much to be a criminal."Chapters:00:00 Cyber risk engineering and emerging AI risks, live at ITC 202600:24 First time in Vegas and the original attention hackers02:09 Growing up in London and wanting to be a chef05:25 Mechanical engineering and wind turbines in Peru06:05 Falling into cybersecurity in 201610:06 When cyber stopped being a game and became a board issue11:06 Insurance, the honeypot of data12:10 From banks and government to insurance13:08 What Mosaic does: Lloyd's syndicates and skin in the game14:13 Two hats: CISO and cyber risk engineering lead16:06 The disconnect between the CISO and the cyber insurance buyer18:32 A criminal marketplace that runs like a business19:57 Phishing written by AI and the end of the easy tells21:21 No urgency, no link22:59 "How would I hack Mosaic?" and synthetic voice attacks24:49 What keeps Jay up at night: the basics26:34 Moving goalposts: MFA, passkeys and biometrics28:09 Frontier AI and 26-year-old vulnerabilities29:29 People doing stupid things: the gift card scam30:05 Using AI as a proactive pen tester31:01 Why defenders adopt AI slower than attackers31:59 The people pleaser problem and wrap up🔗 Connect:Jay Vinda: https://www.linkedin.com/in/jayvinda/Mosaic Insurance: https://www.mosaicinsurance.com | https://www.linkedin.com/company/mosaic1609👤 Host:James Benham: https://www.linkedin.com/in/jbenham🎙️ 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! 🤓
- Sep 18, 202628 min
Claims Transformation and Operational Excellence with David Fernandez from Kingstone Insurance
David Fernandez, Chief Claims Officer at Kingstone Insurance, joins host James Benham to explore claims transformation, operational excellence, and why the team comes before the technology.David fell into claims almost by accident: a broken-down car and a newspaper ad for a claims rep trainee job at Progressive, one that came with a company car, started an 18-year run there. A decade at Liberty Mutual followed, then stops at Unum and Point32Health, and now three years as Chief Claims Officer at Kingstone Insurance, where he has helped lead the company's turnaround.In this episode:• Claims quality is a grind, not a project. It is won file by file, day after day, until it becomes how the team works, not something you launch and move past.• Why "until you have a team that you believe in, you're swimming up river" is the foundation every other fix in a claims org sits on top of.• How a small, empowered team rebuilt Kingstone's claims platform in four months, with clear ownership and not a single slide deck.• Why making no decision is worse than making a suboptimal one, and how giving people room to admit mistakes keeps a transformation moving.• Inside Kingstone's catastrophe playbook, built for a Northeast climate that delivered 11 declared catastrophes in the first quarter alone.Key Quotes:"We sell a piece of paper and a promise. Sometimes it's a PDF.""Making no decision is worse than making a suboptimal decision.""Until you have a team that you believe in, you are swimming up river.""There was not a single slide for that whole thing."🔗 Connect: David Fernandez, Kingstone Insurance links👤 Host: James Benham🎙️ Terra sponsor block + InsurTech Geek socials + standard sign-off (unchanged, copied from the standing footer)
- Sep 4, 202623 min
Innovation Ecosystems and Global Market Transformation with Dawn Miller from Lloyd's
Dawn Miller, Chief Commercial Officer of Lloyd's and CEO of Lloyd's Americas, joins host James Benham to explore what an insurance ecosystem actually is, why a 338-year-old market still has to fight to be understood, and how Lloyd's Lab turned an accelerator into a pipeline that keeps its alumni in the industry.Dawn grew up in Georgia and went to university in Washington, D.C. planning to run the United Nations. Instead she found risk transfer — first at OPIC, now DFC, then political risk at Willis — and stayed for 25 years, through Chubb, AXA and AIG, with a detour building a company in Prague along the way. She joined Lloyd's for the transformation challenge: an institution with 338 years of legacy, a license network trading in 200 countries, and a purpose statement that needed a reset.Recorded on site at InsurTech Insights New York 2026.In this episode:• What separates an ecosystem from a marketplace or a network — Dawn's answer is the heartbeat at the center, where you can watch value move between stakeholders• Why Lloyd's reset its purpose statement in March, and why "global" appears in it twice when 60% of market premium comes out of North America• The narrative problem: a coffee house origin story and 338 years are not enough to win capital and clients• Inside Lloyd's Lab seven years on — two themed cohorts a year, structured problem statements, government partners, and the 95% of alumni still in insurance• Why insurance should talk about itself as a resilience industry that happens to sell insurance, and what that reframe does for talentKey Quotes:"We bring together the world's leading risk-takers to advance global progress.""Your competitor one day could be your partner the next, your client the following.""We can't just say we started in a coffee house. We've been here 338 years. That's not enough.""Ecosystem is the only word that gives a sense of a bit of a heartbeat to the center of it.""Talk about us as a resilience industry that happens to sell insurance."🔗 Connect:Dawn Miller: https://www.linkedin.com/in/dawn-mmiller/Lloyd's: https://www.lloyds.com | https://www.linkedin.com/company/lloyd%27s-of-london/👤 Host:James Benham: https://www.linkedin.com/in/jbenham🎙️ 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! 🤓
- Jul 31, 202643 min
Claims Automation, AI Adoption & The Future of Adjusting
Ken Bunn, Vice President of Claims at Builders Mutual Insurance Company, joins hosts James Benham and Rob Galbraith to explore how a construction only Southeast insurer built its claims department from scratch, why the AI tools that stick are the ones adjusters never have to think about, and what it takes to keep training junior adjusters into seniors.Ken's path ran through 18 years at Nationwide, rotating between claims leadership, field training, and IT program management, before Builders Mutual asked him to build a claims department that didn't exist yet. Twelve years later, the company has grown from roughly 200 million to 650 million in revenue, and Ken still leads much of the original team he brought over from an outsourced TPA.In this episode:• Why Builders Mutual pulled its claims department in-house, and how they kept close to 30 of the original 40 people they brought over. • The predictive AI models that worked exactly as designed and still failed to stick. • The unglamorous automation, document routing, indexing, and med record summaries, that actually delivered the ROI. • Ken's leadership philosophy for change management with no formal program at all. • Why work comp rate softening may be hitting a floor as catastrophic claims costs climb. Key Quotes:"You can't work on an assembly line and do brain surgery at the same time.""It's not going to solve all your problems. It's going to help.""There might be something wrong when your claims adjusters are the happiest people in the room.""Be real. Tell people what's going to happen and why you're doing it.""Pick and choose your tools well so they inform the adjuster, not just replace them."🔗 Connect:Ken Bunn: https://www.linkedin.com/in/kenbunn/Builders Mutual Insurance Company: https://www.buildersmutual.com | https://www.linkedin.com/company/builders-mutual-insurance-company👤 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! 🤓
- Jul 10, 202635 min
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.
- Jun 26, 202637 min
Ep. 180: The Future of Cyber Insurance and Parametric Risk
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
- Jun 12, 202642 min
Access, Operations, and Scale: Rethinking the Insurance Market with PoloWorks
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.
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