The Future of Insurance

Episode Detail

Recorded live in front of senior Claims leaders, this panel episode of The Future of Insurance brings together two founders rethinking long-standing parts of the property claim. Curtis Kincaid, Founder & CEO of Scopeworx, and Alexis Vertefeuille, Founder & CEO of Sinistar, join Bryan Falchuk to talk about where AI and market data are making a real difference in Claims today, and where they still fall short.

Curtis explains why a general-purpose chatbot can't produce a roof estimate a carrier can defend, and how guided inspections and live, weekly labor and material pricing produce consistent results inside Xactimate and Cotality. Alexis describes how a bidding marketplace for temporary housing has sped up placements for displaced families while lowering costs, and why carriers should keep their data organized and in-house as owning their own AI becomes realistic. The conversation also covers AI bias versus human bias, the risk of AI "wrappers," slow adoption cycles, and how the adjuster's role is changing.

Guest Bios

Curtis Kincaid is the Founder & CEO of Scopeworx, a roof estimating marketplace that produces third-party, unbiased roofing estimates for property claims. He has more than 15 years of experience in insurance and restoration. From 2004 to 2018 he worked in catastrophe adjusting and management, and he then built and led a 17-person estimating firm that produced and settled more than 200,000 estimates. He founded Scopeworx to bring balance and speed to roof claims by giving carriers, contractors, adjusters, attorneys, and homeowners the same transparent, market-based pricing.

Alexis Vertefeuille is the Founder & CEO of Sinistar, an AI-enabled temporary housing platform built for insurance claims. He started the company in Quebec after helping a friend's mother who had been displaced by a house fire and spent months in a hotel. He went on to build a bidding marketplace where vetted local hosts compete to house displaced policyholders in furnished homes. He holds a law degree from Université Laval, which he completed while founding Sinistar. He was named to the 2024 Forbes 30 Under 30 North America list in the Social Impact category.

This episode was recorded live at the 2026 JCEA Annual Fall Meeting.

Show Notes:

Bringing the Market Into the Claim:

• Competition for every relocation: Sinistar invites hosts to bid on each temporary housing placement, which widens supply and, per Alexis, has lowered temporary housing prices by about 15%.

• Pricing that reflects today: Scopeworx tracks labor from about 3,500 contractors and pulls material pricing by API, updating every Friday, so estimates hold up even when a major CAT event moves the market.

• Historical data has its own bias: Curtis notes that carrier data built on past settlements reflects past guidelines and negotiations, which live market data helps avoid.

Where General-Purpose AI Falls Short:

• Same prompt, five answers: Curtis's team ran an identical prompt through the same chatbot five times and got estimates up to 30% apart, a result no carrier could defend.

• AI where it fits: Scopeworx uses AI for routine work like letters, notes, and homeowner texts, and keeps guardrails on estimating, with guided inspections mapping directly to line items in Xactimate or Cotality.

• Beware the wrapper: Alexis cautions against tools that resell general-purpose models, and says trustworthy AI is trained on one specific decision, much as autonomous vehicles orchestrate task-specific agents.

Bias, Trust, and Owning Your Data:

• The human side of bias: Bryan asks why AI bias draws scrutiny that human bias rarely does. Alexis sees a need for independent testing to show an AI isn't tilted toward profit or particular suppliers.

• Your model, your priorities: Alexis expects carriers to own or rent models trained on their own data, built around their own priorities on price, quality, or communication, and urges them to organize their data and keep it in-house.

• Two estimates, one choice: Scopeworx can build a carrier's guidelines into an estimate and also produce one without them, so adjusters can see a public adjuster's challenge coming. Carriers that don't want the second estimate can toggle it off.

The Adjuster's Role Going Forward:

• Seven files an hour: One IA firm cut a 40-minute estimate-writing task to under five seconds, landing within about five cents of the handwritten result and lifting output from about one and a third files per hour to around seven.

• The decision stays human: Curtis wants adjusters to be more efficient, and points out that the settlement decision still belongs to the adjuster until laws and comfort levels change.

• Consistency across the street: Technology-driven estimates help keep neighbors with similar losses from getting very different results from the same carrier.

• The expertise pipeline: Bryan raises a longer-term concern: if AI takes the simpler claims, the Industry needs new ways to develop expertise in its next generation of adjusters.

Advice for Claims Leaders:

• Speed of adoption matters: Curtis warns that tools change so quickly that slow evaluations miss the moment. One carrier took three and a half years to go from proof of concept to adoption.

• Get your data right: Alexis urges carriers to organize, classify, and name their data now, so they're ready as owning their own AI becomes affordable.

• Action today: Bryan closes with the point that there are real steps to take now, from preparing data to moving forward with solutions already having impact.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Detail

A comment at a claims conference sparked this solo episode of The Future of Insurance: at events across the Industry, it can feel like everything is AI now. Bryan Falchuk takes that reaction seriously. The numbers rarely support it, but the discomfort behind it is real, especially for professionals in restoration, contracting, and other hands-on parts of Claims who are watching change swirl around their work.

Bryan argues that discomfort is a signal worth following. Drawing on a talk by Jessica Eldridge, SVP & Practice Director of Cyber at J.S. Held, on the overlap between cyber and property risk, he shows how AI-driven data centers are creating new physical exposures, and how AI's growing role in supply chain management touches even the most traditional trades. Digging in may reveal an opportunity, or lead to the informed conclusion that a trend doesn't affect you yet. Either way, you come out better prepared. When change feels uncomfortable, that's the moment to get curious.

Show Notes:

When It Feels Like Everything Is AI:

• An attendee at the Virginia State Claims Association conference told Bryan that PLRB events feel like they're all AI now.

• In practice, AI and tech account for under 30% of vendors and sessions at PLRB events, including its innovation-focused summit.

• The percentage matters less than the perception. For people in traditional, physical parts of Claims, the change feels like it's everywhere, and that's uncomfortable.

Discomfort as a Signal:

• Bryan suggests treating discomfort as a sign of change happening around your work, even when it isn't directly in your work.

• Worries about AI and jobs are valid, and there are real arguments on both sides, which is exactly why understanding the dynamics matters.

• Bryan has explored this tension in his writing on what AI could mean for the agent and broker channel.

Where Cyber Meets Property:

• Jessica Eldridge, SVP & Practice Director of Cyber at J.S. Held, spoke at the same event on the interplay between cyber insurance and property.

• Data centers carry major property exposure during construction and once built, and they are attractive cyber targets.

• Bryan points to a recent case in France where refrigeration settings in grocery stores were altered, causing spoilage and, in some cases, fire. Data center cooling faces the same kind of risk.

• For restoration and contractor firms working in commercial spaces, understanding these risks could open new opportunities or inform a decision to stay out.

Even Traditional Work Runs on a Supply Chain:

• Construction, auto repair, and restoration all depend on materials and tools moving through supply chains.

• COVID showed how disruption can stop work entirely, and tariffs and geopolitical conflict keep the pressure on.

• AI is increasingly used to route goods around those constraints, so it reaches physical trades whether they engage with it or not.

Get Curious: Digging in may lead you to conclude that a trend doesn't affect you, but you'll have reached that conclusion informed and you'll be ready if it changes.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Detail

Cyber insurance has changed what it delivers to policyholders twice in roughly 15 years: first with breach response, and then with outside-in scanning that helps a business become a better risk before it is ever quoted. Caroline Thompson helped build both. In this episode, Bryan Falchuk talks with Caroline, CUO, Operations at At-Bay, about what she saw at the forefront of those shifts, how At-Bay's InsurSec model pairs every policy with security services for small businesses that lack the people to defend themselves, and why VPNs became one of the clearest signals of risk in cyber.

Looking ahead, Caroline shares why she believes the cyber market is due for consolidation, why AI exposure is so hard for underwriters to separate from AI marketing, and where she sees the next gap: personal cyber coverage for individuals and executives who are on their own when their personal accounts are compromised.

Guest Bio

Caroline Thompson is CUO, Operations at At-Bay, the InsurSec company that pairs cyber insurance with active cybersecurity for small and mid-sized businesses. She brings more than 15 years of insurance experience, much of it spent building underwriting operations from the ground up.

Caroline came into insurance through internships at Catlin in London and Hannover Re, and wrote her senior thesis at Providence College on microinsurance. She built her underwriting foundation at Beazley, where she moved onto the cyber team, followed by roles at Zurich North America and Argo Group.

In 2019 she joined Cowbell as its 13th employee and head of underwriting, becoming part of the founding leadership team. She created Cowbell's Prime 250 product and led its form filing and acceptance in all 50 states, rising to SVP of Underwriting and Reinsurance and then Chief Underwriting Officer. She later joined Elixir, a newly launched AI-driven cyber MGA, as Chief Underwriting Officer, before joining At-Bay, where she served as Middle Market CUO before taking on her current role.

She was named a Business Insurance Break Out Award winner in 2021. A former nationally competitive synchronized swimmer, she says she enjoys the early, ambiguous stage of building a team, framework, or process from scratch.

Show Notes:

Two Shifts That Redefined Cyber Insurance:

• Breach response becomes standard: At Beazley, Caroline watched cyber grow from an infosec tower into a policy with a response team built in, now a component of nearly every cyber policy.

• Underwriting before the loss: A wave of InsurTech MGAs began scanning a prospect's outside perimeter at scale to understand the risk, and make it better, before binding.

• Why it had to change: Paper submissions and the time it took an underwriter to get a quote out were never going to scale.

Data as an Early Warning System:

• The volume of data: What surprised Caroline most on joining At-Bay was the sheer amount of data available to assess each individual risk, with research and risk teams constantly looking for trends and red flags.

• VPNs as a signal: At-Bay was early to identify VPNs on customers' systems and alert them to next steps, an indicator of compromise the rest of the market later came to recognize.

What InsurSec Means in Practice:

• Insurance and security under one roof: At-Bay's insurance company and security company both report into the same parent.

• Built into every quote: Every package includes some free security services plus an InsurSec option with deeper protection, including the Stance platform and managed detection and response (MDR).

• Help small businesses can't staff on their own: Policyholders can send a suspicious email or a request to change wire instructions to At-Bay's team and get an immediate answer on whether it's safe.

Joining Munich Re: Caroline on At-Bay's long relationship with Munich Re and why joining the Munich Re family under HSB makes sense.

A Market Due for Consolidation:

• Too many players: Caroline believes the number of MGAs that sprang up in cyber isn't sustainable, and that consolidation is needed and already underway.

• The end of the runway: Many MGAs are reaching the end of their funding and facing a decision on what comes next, as technology that once stood out becomes more common.

• MGAs as the Industry's lab: Bryan frames this cycle as how new exposures get worked out, with innovation in MGAs eventually folding into larger organizations.

AI Exposure and the Underwriting Challenge:

• Real AI risk versus AI marketing: Every market is struggling to separate true AI exposure from operational risk or AI branding, much like companies adding ".com" to their names in the early 2000s.

• New skills and tools: Underwriters need training to assess it, and carriers need to build or buy tools to understand it at scale.

• Room for specialists: With much of the market staying quiet on AI, Caroline sees opportunity for niche MGAs with AI liability-specific products.

The Personal Cyber Gap:

• Individuals on their own: Friends, family, and executives face real breach risk, with few products to help them recover.

• Possible paths: Coverage could come through the company's cyber or D&O policy extending to the C-suite, or through a standalone personal product.

• Beyond credit monitoring: What people need is hands-on, concierge-style help regaining control of accounts and dealing with fraud filed in their name.

• The scale challenge: Small personal premiums need scale to justify the investment, so brokers pushing their carriers can help.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Detail

Claims professionals often begin a conversation already cast as the adversary. Many claimants have been primed to expect a fight, so they arrive ready for one, and the person trying to help has to find a way through that before anything productive can happen. In this solo episode of The Future of Insurance, Bryan Falchuk shares the framework behind his keynote at the Western Loss Association Fall Conference: the 50 75 100 Solution, an approach to making tough relationships work better by recognizing how much of any difficult interaction is within your influence.

The episode features Bryan's TEDx talk from Pensacola, where he first laid out the approach. Drawing on three Buddhist principles (happiness seeking, interdependence, and impermanence), he explains why owning your half of a relationship gives you influence over three quarters of it, and walks through a workplace conflict where choosing not to fight back changed the outcome. The ideas apply equally to a tense claim conversation, a difficult colleague, family, or a one-time encounter with a stranger. Whether or not you caused a difficult relationship, you can still be the one who changes it.

Show Notes:

Why This Matters in Claims:

• Many claimants arrive expecting a fight, shaped by messaging that tells them their insurer is on the other side.

• The adjusters who see past the initial hostility and stay focused on helping are the ones who move a difficult interaction somewhere far more productive.

• The framework is the basis of Bryan's keynote at the Western Loss Association Fall Conference, and he has shared it with adjuster groups and carrier claims teams in training.

Three Principles Behind the Approach:

• Happiness seeking: Everyone acts in pursuit of their own happiness. When someone's actions cost you, it is usually not about you, which makes it easier not to feel attacked or bite back.

• Interdependence: No one is all good or all bad. People behave differently in different situations, so changing the situation can change the dynamic.

• Impermanence: Everything can and will change, which is exactly why the effort is worth making.

The Math: 50, 75, 100:

• 50: Every relationship has two sides, and you own your half.

• 75: Your half splits into actions and reactions. The other person's reactions are based on what you put out, so owning your half influences half of theirs, giving you influence over three quarters of the relationship.

• 100: When you can sway three quarters of a problem, you can build quickly toward a fully better relationship.

A Workplace Case Study:

• A highly respected colleague emailed Bryan and their boss a list of his supposed failures, many of which were inaccurate.

• Rather than refute each point or counterattack, Bryan thanked her, set the debate over whose data was right aside, and proposed meeting on the underlying business issue.

• In the meeting he stayed calm, let her finish, and asked what she actually wanted to happen. Her answer was a good idea, and he offered to help make it happen.

• It didn't make them close friends, but the attacks stopped and they could work together productively from then on.

Being the Water: Bryan closes with a Buddhist teaching about conquering anger with non-anger: fire is not put out with more fire, and even in the most heated situations, you can choose to be the water.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Detail

John Kellington has spent his career on every side of the same question: how does data move reliably across an industry built on thousands of separate systems that all need to talk to each other? He's built the standards, lived by them as a carrier CIO, and now, as the new CEO of ACORD, he's back to run the organization that sets them for the entire global insurance industry.

In this conversation, Kellington and Bryan dig into what ACORD actually does beyond its well-known forms library, why AI in insurance can only be as trustworthy as the data underneath it, and how a reference architecture built inside IBM more than 30 years ago is still shaping how the industry should think about modeling risk today, including the messy, high-volume data coming from connected cars and IoT devices that doesn't fit neatly into any existing field.

Guest Bio

John Kellington is the Chief Executive Officer of ACORD (the Association for Cooperative Operations Research and Development), the insurance industry's global standards-setting body. He returned to ACORD in August 2026 after 16 years as Executive Vice President and Chief Information Officer of The Cincinnati Insurance Company, where he applied an architecture-led model to transform the carrier's technology operations. Kellington began his career at IBM, then spent seven years as a carrier technology leader at Ohio Casualty (later acquired by Liberty Mutual). He previously spent three years at ACORD as Senior Vice President of Standards Development, Information Technology, Corporate Finance and Membership, where he helped develop what is now known as the ACORD Reference Architecture.

This episode was recorded live at ACORD Connect 2026.

Show Notes:

What ACORD Actually Does:

• Reach: roughly 30,000 participants worldwide set data exchange standards across the global insurance industry through ACORD, not just forms.

• Still forms, but not only forms: ACORD maintains roughly 800 to 900 active forms, but the bigger job now is electronic data exchange, getting carrier, agency, and vendor systems to talk to each other in the same format.

• Where competition actually lives: exchanging data isn't a competitive advantage. What a carrier does with that data in underwriting, pricing, and service is where the real competition happens.

Why ACORD Has to Stay Independent:

• Owned by the industry: ACORD runs on membership dollars, not venture capital or any single company, which Kellington says is the only reason it can set standards without an agenda.

• "Switzerland": his own word for ACORD's role. Not a vendor, not a carrier, not a broker, just an organization funded to make the industry work better.

• The line it won't cross: if ACORD ever competed directly with the vendors and carriers it serves, he says it would lose the credibility to set standards for the industry.

AI Needs Trust Before It Needs Anything Else:

• The core argument: AI can only "flourish" in insurance if it's built on data that is consistent and traceable, exactly what standards provide.

• "Invent from here": Kellington's framing for the industry's next move. Build on the existing standardized data pipeline rather than reinventing it from scratch.

• AI as the bridge: he sees AI solving the industry's hardest data problem, the huge volume of freeform text and inconsistent formats that never fit neatly into a standard field.

The ACORD Reference Architecture, Explained:

• Where it came from: intellectual property IBM and Prima Solutions donated to ACORD, building on modeling work IBM's research team did decades earlier. Kellington helped bring that donation in.

• What it is: Kellington calls it the most advanced model of the insurance world in existence, broad enough to represent literally anything that can be insured.

• What it did for one carrier: he personally used it to transform Cincinnati Insurance's IT organization, driving reuse, lower cost, and higher software quality across the company's systems.

What the Industry Needs to Do Its Part:

• Start with distribution: when agents and brokers voice a need clearly, carriers listen, and when carriers listen, vendors follow.

• Build a community, not just a standard: Kellington wants an "architecture community" of the people who actually work inside these systems, improving the Reference Architecture together rather than leaving it to ACORD alone.

• His near-term goal as CEO: define a clear future state for how the industry's tools should work together, then map the practical steps to get there.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Detail

Three voices, one shared problem: the insurance industry calls itself data-driven, but trusts almost none of the data it runs on. This episode is a live panel recorded at ACORD Connect 2026, where Bryan sat down with Russell Sommers of Baker Tilly, Meredith Barnes-Cook of Datos Insights, and Spero Zacharias of Chubb to talk about what happens to that trust problem once AI starts doing the interpreting.

The conversation moves through where AI genuinely closes the industry's biggest data gaps and where it just introduces a new category of things to verify, why the fixed-field data governance models built for a different era might not survive an AI-driven one, who actually owns a piece of data when something goes wrong, and how far state regulation and industry standards like ACORD's can go toward building trust before the technology outruns both. A live audience Q&A closes out the session, pushing the panel further on legacy data, ownership, and industry-wide collaboration.

Guest Bio

Russell Sommers is a Principal at Baker Tilly, where he leads the firm's New York financial services risk advisory practice. With more than 15 years helping insurers, banks, and financial institutions navigate governance, risk, and compliance, he specializes in IT risk and cybersecurity and leads Baker Tilly's IT and cybersecurity examination practice on behalf of more than 30 state departments of insurance.

Meredith Barnes-Cook is a Senior Principal at Datos Insights, with nearly four decades in insurance operations and technology. She began her career at Liberty Mutual, where she spent 33 years in leadership and executive roles across digital, product, and organizational transformation, and went on to build go-to-market strategy at an AI customer experience company before joining Datos Insights. Her current research centers on P&C rating and underwriting technology and, notably for this episode, agentic AI governance.

Spero Zacharias is SVP, Global Information Technology, Major Initiatives at Chubb, a role he has held since 2021, directing a portfolio of cybersecurity programs spanning 54 countries and all of Chubb's commercial and consumer lines. He brings more than three decades in insurance technology and cybersecurity, and deep standards-body pedigree: he chaired the ACORD board from 2017 to 2019 and currently chairs the board of ACORD Solutions Group.

The industry doesn't get to wait for someone else to define what trustworthy data looks like. It has to decide that for itself, before AI makes the decision by default.

This episode was recorded live at ACORD Connect 2026.

Show Notes:

The Trust Deficit in Data:

• Statistics don't lie, but liars use statistics: Russell Sommers on why the danger isn't usually intentional fraud, but confirmation bias — pulling data to prove what you already believe instead of using it to find out what's happening.

• The same dynamic that drives the industry's "we can't because" pattern gets amplified everywhere by social media and deepfakes, where trust itself becomes the thing that gets exploited.

AI as Enabler and Complication, at the Same Time:

• Spero Zacharias framed the core tension of the episode: AI can finally solve for the data handcuffs the industry has lived with for decades, but introduces a new set of verification problems in the process.

• Intelligent document processing is finally unlocking the 80–90% of insurance data that arrives unstructured — but when AI gets the interpretation wrong, human critical thinking becomes more essential, not less.

• The panel drew a hard line between AI making a recommendation a human reviews and agentic AI taking an autonomous action — the stakes for verification change completely once AI is deciding, not just suggesting.

A Governance Model Built for Fields, in a World That Has Outgrown Them:

• The panel challenged whether traditional, fixed-field data governance still fits a world where AI-processed data doesn't arrive pre-labeled and well-defined.

• One reframe from the conversation: shift governance thinking from which fields are required to which risk signals need to be captured.

• The closed claim review is being rethought as continuous, real-time monitoring — catching a bad AI recommendation while it's happening, not years and thousands of transactions later.

Data Ownership Has to Have a Name Attached:

• The clearest agreement on the panel: data accuracy has to be business-owned, even when a technical or data function builds and maintains the systems around it.

• A chief data officer can build the infrastructure, but without a named owner accountable for a specific data element's quality, governance models fail on paper or not.

• Real example: a claims system that used the same word, "death," for three different drop-down values for 15 years, with no institutional memory of what distinguished them.

Standards as an Enabler, Not a Floor:

• Spero Zacharias, drawing on his ACORD board chairmanship: standards exist to anchor an industry to something shared, not to give companies a minimum bar to clear and stop.

• State regulation, NAIC guidance, and ACORD standards are minimum requirements — the panel's challenge to the industry is to build past the floor rather than manage down to it.

• Russell Sommers connected this to compliance: state privacy laws, NAIC's responsible AI principles, Colorado's AI law, New York's Circular Letter 7, and a new NAIC exposure draft on third-party AI use.

Cybersecurity's Human Element:

• Spero Zacharias pointed to the Scattered Spider social engineering attacks, where public data was used to get two-factor authentication credentials reset at multiple insurance companies.

• The most recent Verizon Data Breach Investigations Report shows AI-enabled vulnerability exploitation rising sharply, even as the panel argued AI-assisted development should make software more secure over time.

An Audience Question on Industry-Wide Collaboration:

• With real-time data connectivity and API integration now possible, the industry has an opening to stop re-keying the same data across broker, insurer, and reinsurer systems.

• The panel pointed to the London market's Solutions Group as a model North America could learn from in building shared, collaborative data infrastructure.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

We're taking a quick break this week as we ramp up with a lot of interviews being recorded in the next month.

Stay tuned and be sure to subscribe you catch them when they start dropping on September 22nd with Season 9 Episode 6!

Episode Detail

This episode is a discussion of the thought leadership paper Bryan Falchuk published in September 2026 on a pressing an important question the industry is facing today – will AI spell the end of insurance agents and brokers?

AI is not going to kill the insurance agent channel. That's not really in dispute, and it was never the right question. In this solo episode, Bryan Falchuk argues that the public debate over AI and agents has been fought almost entirely on the wrong terrain — demand — when the real disruption is on the supply side. Buyer demand for a trusted expert on a complicated, high-stakes decision is as durable as ever, but that says nothing about how many people will be doing that work five years from now, or how much of it AI will be doing on their behalf. Bryan traces the argument through a real disagreement with fellow industry voice Matteo Carbone, a landscaping-business example of what agentic AI can catch that no human ever sees, and the two mechanisms he thinks actually create opportunity inside this disruption: Empowered Expertise and Market Expansion.

The channel isn't disappearing. How it's staffed, and by whom, is about to change faster than most of the industry is planning for.

Show Notes:

The Real Question: Demand vs. Supply

• Demand isn't the debate: Bryan agrees the agent channel survives — buyer demand for a trusted expert on a complex, infrequent, high-stakes decision isn't eroding.

• The real question is who or what does the work inside the channel five years from now.

• A channel can hold 100% of its market share and still be staffed by a fraction of today's headcount, partly by AI standing in an agent's seat.

Where the Reframe Came From: The Matteo Carbone Debate

• The idea grew out of a real disagreement with Matteo Carbone, Founder & Director of IoT Insurance Observatory, who argues buyers won't shop and transact alone for something this complicated. Bryan agrees.

• Bryan's pushback: demand-side evidence, like low churn, doesn't say anything about how much of the work AI ends up doing.

• His read: most of the public debate is arguing past itself over demand when the actual disagreement, if there is one, is about supply.

Accountable Delegation, Reconsidered

• Bryan is skeptical people consciously want a human to blame if something goes wrong, rather than offloading the cognitive burden onto someone trusted to have done the homework.

• Why it matters: wanting someone to blame is human-only, but wanting a trusted expert to carry judgment is something AI can plausibly meet.

• We already do this elsewhere, the same way fraud alerts and wearables already quietly do, without anyone consciously choosing to delegate.

Why This Time Is Actually Different

• The Internet never displaced agents because it's a transaction engine, built for buyers who already know exactly what they want. Insurance is sold, not bought.

• Most buyers need someone to translate a messy, real-world situation into the right coverage, which the Internet was never built to do.

• AI can build context: interviewing a buyer, pulling outside data, mapping risk, and comparing it against policy language — the same judgment work a good agent does, at a scale one person can't match.

Prompted AI vs. Agentic AI

• Most AI-and-insurance conversations assume a prompted model: a chatbot a person has to remember to open, which still requires someone to decide "today I'll think about my insurance."

• Agentic AI removes that requirement — in Bryan's landscaping-business example, an AI system already handling her scheduling and contracts catches a new tree-removal service line and flags the coverage gap before she or her agent notices.

• The real disruption isn't a friendlier chatbot: it's AI finding the need on its own, before anyone on either side of the transaction has done anything at all.

Agents Are Already Leaning on AI, and It's Not Speculative

• David Embry, CEO of Mylo, described building AI that gives brokers a constantly current view of market rates and appetite instead of trying to hold it all in their head.
• Jason Cass has talked about agentic AI absorbing a large share of an agency's operational load, from paperwork to quoting, letting the same team handle more business with fewer people.

• Layered on top: agents are retiring faster than they're being replaced, and AI is what lets the channel hold its market position anyway.

The Opportunity Side: Empowered Expertise and Market Expansion

• Empowered Expertise: AI that continuously tracks the market doesn't replace an agent's judgment — it gives them the raw material to use it faster.

• Market Expansion: the same pattern that built the Cyber insurance category is playing out with AI liability, data mishandling, and bad AI-generated work — exposures that need an expert to explain and sell coverage for them.

• Carriers are already excluding AI liability, and ISO is updating standard policies to do the same, while startups like Testudo build coverage specifically for that gap — raising the need for an agent's help, not lowering it.

Why Humans Stay Essential: Analytical vs. Critical Thinking

• Bill Pappas, EVP and Global Head of Technology and Operations at MetLife, distinguishes analytical thinking (patterns, logic, volume) from critical thinking (judgment in ambiguous situations).

• AI is winning the analytical work, and Bryan doesn't think that's a fight worth having.

• The future isn't humans competing with AI for the same slice of work: it's AI taking the analytical load off agents entirely so they can spend nearly all their time on the critical thinking that was always the hardest part of the job to replace.

Timing: Faster Than Most Are Planning For

• The cultural barrier to trusting AI with consequential decisions is already gone — today's buyers have spent their adult lives doing complicated things online.

• The technology curve is compressed: almost none of what looks like a real threat to agents existed three or four years ago, and it's advancing every few months, not years.

• Bryan's call: real, visible change inside the next five years, with the leading edge already visible in the next two to three.

What To Do About It

• Agents: stop treating analytical work as where your value lives, start using AI tools in your actual daily workflow now, and invest in judgment and relationship skills.

• Agency leaders: stop staffing to today's agent-to-book ratio, and shift training budget toward critical thinking and complex-case skills.

• Carriers: production is decoupling from agent headcount. Give appointed agents real AI tools or lose them to carriers who do.

Free White Paper: The full argument, including the complete demand-versus-supply reframe and the mechanics of Empowered Expertise and Market Expansion, is laid out in Bryan's new white paper, The Future of Agents & AI, free to download at future-of-insurance.com/agents.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Detail

When wildfire risk pushed many insurers to retreat from the California homeowners market altogether, CSAA Insurance Group chose a different path: reward the homes that actually harden against fire with a three-year rate guarantee and a discount of up to 30 percent, and keep writing business through it. In this conversation, Mike Zukerman, President and CEO of CSAA Insurance Group, joins Bryan Falchuk to talk about what that choice has actually looked like inside a company that insures around 600,000 California homes, why he believes a healthy, competitive insurance market serves customers better than any single carrier cornering it, and how CSAA is using AI to give its claims and customer service teams more room for empathy rather than replacing them. They also get into what it takes to hold a culture together across a workforce that is 97 percent remote, and why Zukerman thinks the basics of caring about a customer, even when the answer is no, still decide who wins a soft market. Every choice Zukerman describes here, the underwriting, the AI, the culture, comes down to the same discipline: doing the harder, more proactive thing on purpose instead of waiting for a crisis to force it.

Guest Bio

Mike Zukerman is President and CEO of CSAA Insurance Group, a AAA insurer serving members across 23 states and Washington, D.C. He was appointed to the role in May 2024 after serving as interim CEO since August 2023, succeeding Tom Troy. Zukerman joined CSAA Insurance Group in 2011 as Chief Legal Officer, a role he held for roughly twelve years, and also served as the company's acting Chief Operating Officer in 2014. Before joining CSAA, he spent about two decades in technology and legal leadership roles, including at GeoVera Holdings, Critical Path, Sega, and Netopia. He holds a law degree from American University and a bachelor's degree from UC Berkeley, where he has also guest-lectured at the Haas School of Business on law and entrepreneurship. He was named 2017 Corporate Counsel of the Year by the San Francisco Business Times. Zukerman serves on the boards of the American Property Casualty Insurance Association (APCIA), the Bay Area Council, and Keep Tahoe Blue.

Show Notes:

Wildfire Risk: Rewarding Home Hardening, Not Retreating From It:

• CSAA guarantees at least three years of coverage, plus a discount of up to 30 percent, for any home that meets the IBHS Wildfire Prepared Home standard.

• Zukerman says CSAA has non-renewed at most about 2 percent of its book, even as other carriers stopped writing new homeowners business in parts of California entirely.

• Despite the state's reputation, Zukerman cites a LendingTree study ranking California the eighth-cheapest state for homeowners insurance, behind Oklahoma, Nebraska, and Colorado.

• Zukerman wants more competitors back in California, not fewer: a robust, competitive market serves customers and the state better than any single carrier absorbing all the risk.

AI as a Force Multiplier for Empathy, Not a Replacement for People:

• CSAA remains a high-touch business by design: callers reach people in the US, even as some competitors move claims intake to agentic AI.

• AI now listens in on claims calls and generates the summary, freeing the person on the phone to focus on the customer instead of scrambling to document everything, and it can catch details, like a passing mention of back pain, that a stressed human might miss.

• Zukerman compares the shift to the arrival of ATMs: bank tellers didn't disappear, they were up-leveled to more judgment-based work, and he expects claims and customer service roles to follow the same path.

• He expects most carriers to lean on agentic AI by default within three to five years, but says CSAA will give customers the choice between a human and AI rather than force one.

Culture and Distributed Work: Humility, Not Proximity:

• About 97 percent of CSAA's roughly 4,000 employees work remotely, split between roughly 3,000 call center staff and 1,000 knowledge workers in underwriting, finance, and legal.

• Zukerman keeps the leadership team meeting every two weeks, in person once a month, backed by what he calls close to zero real constraint on the travel budget for teams to get together.

• He's built the culture intentionally around humility: people feeling safe enough to say "I don't know" or ask for help out loud, which he calls flattering rather than a weakness.

• CSAA runs 14 employee-led culture groups and regular volunteer programs, and recently opened a new office in Phoenix, where the company now employs more people than it does in California.

Customer Delight in a Softening Market:

• Zukerman points to a record: 54 percent of auto insurance customers shopped for a new policy last year, and he expects retention, not new acquisition, to be the growth lever in the soft market ahead.

• He argues delight doesn't always mean solving the problem: even when CSAA can't waive a deductible or has to deny part of a claim, the outcome that keeps a customer loyal is feeling like the person on the phone actually cared.

• He makes the point through an unlikely source: a maddening call with his cable provider that never solved his problem but still left him feeling genuinely cared for.

Career, Liberal Arts, and Learning How to Think:

• Zukerman spent the first half of his career in technology and law before joining CSAA Insurance Group in 2011 as Chief Legal Officer.

• He points to Nvidia CEO Jensen Huang's advice to study liberal arts, and says he gave his own kids the same counsel: use college to learn how to think before specializing.

• He compares AI's disruption to the arrival of the light bulb, noting that new tools have repeatedly reshaped which skills matter without eliminating the need for judgment.

Prior Guests from CSAA Insurance Group

• Ryan Vigus, EVP, Personal Lines Product Management
• Laurna Castillo, SVP, State Product Management
• Debbie Brackeen, Chief Innovation & Corporate Development Officer

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Detail

Insurance carriers have quietly lived with a roughly $50 billion problem for years: a level of fraud baked so thoroughly into homeowners and personal auto pricing that the industry simply calls it the cost of doing business. In this episode, Bryan Falchuk sits down with Kim Garland, Industry Executive & Advisor, to size that number for real and ask why an industry built to manage risk has been so slow to manage this one.

Garland spent more than three decades inside carriers, from GEICO and Safeco to AIG and State Auto, before stepping outside day-to-day operations to advise the industry from a different vantage point. He and Bryan dig into the difference between the old fraud-verification playbook and a newer approach built around trust and behavioral signals, why homeowners insurance can't keep leaning on rate increases the way personal auto has, and what it actually takes for carrier leadership to stop treating a solvable problem as background noise. The takeaway: unlike the weather, this is a lever the industry can actually pull, if it decides to.

Guest Bio

Kim Garland is an insurance industry executive and advisor with more than 35 years of experience across carriers, product management, and actuarial leadership. He began his career at GEICO in 1988, then spent time at Safeco, where he ran the personal auto business until the company was acquired by Liberty Mutual in 2008. He joined AIG in the aftermath of the financial crisis, spending six years helping lead the recovery of its mortgage insurance business. In 2015, he joined State Auto, a regional carrier based in Columbus, Ohio, where he worked until State Auto was also acquired by Liberty Mutual. Since then, Garland has been advising startups and studying the industry from outside its day-to-day operations, bringing a perspective shaped by decades on the inside.

Show Notes:

The Industry Has Priced Fraud In — And Called It Normal:

• Garland estimates fraud costs the industry roughly $50 billion a year across homeowners and personal auto, close to 10% of premium.

• His view: most carriers quietly treat that number as a fixed cost rather than a solvable problem — what he calls one of the industry's "dirty little secrets."

• Honest policyholders absorb the difference every time a carrier accepts a baseline level of fraud and prices around it instead of fighting it.

From Verification to Trust: A Different Paradigm:

• The old playbook asks a question, checks the answer against a database, and accepts that some fraud slips through anyway.

• Newer approaches look at behavioral signals, like how long an applicant hesitates before answering a material question, or a voice-based assessment of trustworthiness, such as the approach used by Clearspeed.

• Garland is careful to separate ordinary rate-shopping behavior, like comparing deductibles or coverage limits, from genuine red flags, like a garaging address that suddenly doesn't match reality.

Trust Is Situational, Not a Life Sentence:

• Today's tools assess trustworthiness in a specific interaction, not as a permanent label on a customer.

• Garland argues that framing matters: someone flagged in one moment isn't branded across every future interaction with the carrier.

Why Homeowners Can't Keep Leaning on Rate Increases:

• Garland sees personal auto and homeowners on different trajectories. Autonomous driving technology is a macro trend that should push auto losses, and eventually premiums, down over time.

• Homeowners insurance has no equivalent tailwind. If rate increases keep outpacing wage growth and general inflation, he expects consumers or regulators to eventually push back.

• His view: when the rate-increase lever stops working, carriers are left with three choices — run at a loss, pull back from the market, or actually attack the underlying cost drivers.

What It Actually Takes to Change: Carrier Attitude, New Tools, Regulatory Room:

• Garland lays out three levers: a genuine change in carrier mindset, which he believes has to be driven from the CEO and C-suite, better trust-based tools, and regulators giving carriers room to push back on bad-faith complaints.

• He argues progress on any one of the three levers moves the needle, even without all three moving at once.

• In his view, the core obstacle is organizational inertia — discomfort with pushing back on a customer complaint, a regulator, or a dip in survey scores, more than any shortage of technology or options.

Predict and Prevent Has Potential, But Human Behavior Is the Real Barrier:

• Garland thinks preventing losses before they happen, not just detecting fraud after the fact, has real legs, particularly for closing the openings fraudulent contractors exploit after a loss.

• He compares the challenge to getting people to save for retirement or exercise consistently: the payoff is real, but delayed, which makes it a hard behavior to change.

• He credits the startups working in this space, while noting that inertia, not a lack of good ideas, remains the biggest obstacle.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.