Full Episodes | Insurtech Leadership Podcast

Introduction When an insurer says no to part of a property claim, how is a homeowner supposed to know whether that denial will hold? Most policyholders can't tell, and most claims are too small to justify hiring a public adjuster. Cameron Mooney, Co-founder and CEO of Tugboat, has worked both sides of that problem, first as an independent adjuster and then as a public adjuster in Los Angeles. In this episode of the Insurtech Leadership Podcast, he talks with host Joshua R. Hollander about how Tugboat helps homeowners handle their own claims, why he sorts every dispute into coverage, scope or price, and what AI-drafted claim letters mean for fair claims handling. Guest Bio Cameron Mooney trained in music therapy and worked in nonprofits before a volunteer trip to Houston after Hurricane Harvey turned into his first job as an independent adjuster, with about a hundred homeowners to call in his first days. He went on to adjust claims across Southern California and became a licensed public adjuster in 2021. At that firm, a claim typically needed about $100,000 in dispute to justify representation, while the average claim he had handled as an independent adjuster was closer to $20,000. That gap led him to co-found Tugboat, which gives homeowners plain-language guidance, help comparing estimates and writing letters, and access to licensed experts for an annual fee instead of a share of the claim. Key Topics -From Harvey volunteer to adjuster: How a podcast tip and a willingness to climb a ladder turned a music therapist into an independent adjuster with a hundred claims to schedule. -The gap public adjusters leave: Why claims under roughly $100,000 in dispute rarely get professional help, and why Cameron wanted a LegalZoom or TurboTax for insurance claims. -Coverage, scope or price: Cameron's three categories for any property claim dispute, and why many disputes involve all three. -Paper or concrete: How Tugboat tells a homeowner whether a denial is likely to fall with another request or will need an attorney. -Setting expectations with data: Why Tugboat now tells users how many letters a dispute usually takes, and how that lowers frustration on both sides. -AI on both sides of the claim: What happens when carriers send AI-drafted letters and policyholders answer with AI tools, and where a real person still has to step in. -Carrier partnerships and claims ratings: The test Cameron applies to any carrier partnership, and his plan to publish claims-handling ratings as Tugboat's data grows. Notable Quotes "Why isn't there a LegalZoom or a TurboTax equivalent in insurance claims?" Cameron Mooney, "I have no incentive to tell them one way or the other that something's covered. I'm not making more money if they get more money." "In an insurance claim, there's a very good chance that at some point you are going to hit a wall." "Claims is always going to be a very human problem." Resources Guest: Tugboat: https://tugboat.claims Cameron Mooney on LinkedIn: https://www.linkedin.com/in/cameronjmooney/ Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast (LinkedIn Showcase): https://www.linkedin.com/showcase/insurtech-leadership-show Subscribe & Review If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Podbean, Apple Podcasts, and Spotify.

Introduction What does a business do when the risk that could wreck its year is one no carrier will write? Event contracts have grown fast on sports and elections, and most of the news about them has been about state lawsuits. Will Brooke, co-founder of Herisson, is working on a different use for them, which is hedging the weather and legislative risks that commercial insurance often leaves out. In this episode of the Insurtech Leadership Podcast, host Joshua R. Hollander talks with Will about how an event contract differs from a parametric policy, how a ski resort could hedge its snowmaking and rain exposure, where wholesale brokers fit, and why he expects event contracts and insurance to sit side by side. Guest Bio Will Brooke is co-founder of Herisson, which he started with Felix Tabary. The founders say they spent years in finance and fintech, including time working on how to price risk, and that running earlier companies left them asking why insurance always comes in the same rigid format and pricing. Herisson says it structures hedges for businesses against one-off risks that insurance doesn't cover, using event contracts that trade on CFTC-regulated exchanges. The company lists Strobe Ventures, Blue Wire Capital and Expansion Venture Capital as backers. Herisson is not an insurance company, and its registration as an introducing broker and commodity trading advisor is pending. Key Topics -Event contracts and parametric insurance: Both pay on a pre-agreed trigger resolved by an objective data source, and Will explains why an event contract doesn't have to be capped at loss the way many hybrid parametric policies are. -A ski resort's weather hedge: How a set number of snowmaking hours at a defined wet-bulb temperature, and rain in tiered bands over key weekends, can each become a yes-or-no contract. -Speed and size: Will says institutional funds will often price a contract in under a week, against weeks to months for a new parametric policy, and that he has seen contracts as small as $500,000 of total exposure. -Legislative and tariff risk: Why an importer facing a jump in tariffs from 10% to 25% or 50% will look seriously at a product it has never used before. -The market is institutionalizing: Block trades, new checks against trading on inside information, and the prediction market desks Will says institutional funds set up this year. -Brokers as partners: Why Herisson positions itself as a non-insurance provider and works with wholesale and retail brokers who keep the client relationship. -Risk management all year round: Will's view that companies will stack insurance and event contracts and manage them as a living system instead of a once-a-year renewal. Notable Quotes "Of the last five ski resorts I've spoken to, [I have] yet to speak to any of them that actually have weather insurance." Will Brooke, Co-founder, Herisson "The pain or the risk exposure that we're talking about is so existential that they're truly interested in engaging in an alternate product." Will Brooke "There is a hundred percent still a place for insurance products to cover risk." Will Brooke "It becomes much more of a dynamic living risk management system for what a company would need versus did we get our policies on the annual date." Will Brooke Resources Guest: Herisson: https://herisson.ai/ Will Brooke on LinkedIn: https://www.linkedin.com/in/williambrooke/ Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast (LinkedIn Showcase): https://www.linkedin.com/showcase/insurtech-leadership-show Subscribe & Review If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Podbean, Apple Podcasts, and Spotify.

Introduction What happens to a startup pitch when every single submission in the pile says AI on it? Stacey Brown has a useful vantage point on that question, because his Innovation Challenge is one of the few places where carriers actually sit down and read what startups send them. Submissions for the 2026 challenge close on October 7, roughly sixty had come in when this conversation was recorded, and Stacey expects the usual rush at the end. In this episode, Josh Hollander and Stacey work through how the challenge is judged, what separates a submission that scores well from one that does not, and why Stacey thinks reviewers this year will spend less time looking at the technology than at the problem the technology solves. Guest Bio Stacey Brown is the founder and president of InsurTech America. He spent more than twenty years as an insurance IT executive before noticing how much investor money was moving into startups built to disrupt the industry, and started reaching out to people around Hartford to talk about it. That became InsurTech Hartford, and by 2023 it had grown enough that he left the day job for it. InsurTech America now runs six regional communities spanning Hartford, New England, Atlanta, Chicago, Florida and the Carolinas, and its Innovation Challenge is in its third year, having drawn more than three hundred startups from over a dozen countries, with winners from Australia, Germany and Israel. Key Topics -AI has stopped being an answer - Everyone is expected to have it now, which means claiming it no longer distinguishes anyone, and Stacey's read is that reviewers will be looking at the problem being solved rather than the tech solving it. -What the 2026 categories actually want - The Hartford is sponsoring the Future of Customer Protection Award for AI and emerging technologies applied to preventing and quantifying risk, and Travelers is sponsoring a prize for the best emerging product or service addressing technological, societal or economic change. -A student track, limited to Connecticut - New this year, and constrained to Connecticut students because of how the state support is structured. -A path to the Startup World Cup - The Innovation Challenge is now an official qualifier for the Pegasus Tech Ventures competition, where the grand prize is a one million dollar investment. -How submissions are judged - Every submission is read by carriers, at least two reviewers each, scored, then narrowed to three finalists per category who present to a panel of judges. Why submitting early matters - Reviewers start on early submissions before the deadline crush, so the same material gets better attention if it arrives sooner. -The new mentor program - Six cycles of two weeks each, with at least one thirty-minute meeting per cycle, structured around product, customer, go-to-market and business strategy, and built to fix the thing that usually goes wrong with mentorship. -Losing can still be worth it - Carriers read everything, so a submission that does not win can still catch someone's interest, and being named a finalist carries its own recognition. Notable Quotes "AI is not the differentiator anymore. You need more than AI." "People aren't going to be looking at the tech as much as they're going to be looking at the problems that are being solved by the tech." "It's amazing how many startups are out there that can't actually articulate who their target buyer is." "If you don't get a strong mentor, you're not going to have a strong experience." Resources Guest: InsurTech America: https://insurtechamerica.com/ Stacey Brown on LinkedIn: https://www.linkedin.com/in/staceybrown/ Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast (LinkedIn Showcase): https://www.linkedin.com/showcase/insurtech-leadership-show Subscribe & Review If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Podbean, Apple Podcasts, and Spotify.

Introduction Carriers are rewriting decades-old systems, and more and more of the new code is written with AI. If the AI that wrote the code is also the thing checking it, who is actually validating what reaches the policyholder? Alex Rodov has spent more than thirty years in software testing, and his answer is that the testing has to be independent and has to start from a complete map of how a carrier's systems actually work. He explains why most carrier testing is still manual, why Emtech keeps AI out of the testing itself, and why the same map turns out to be what a carrier's enterprise AI has been missing. Guest Bio Alex Rodov is the founder of Emtech Group, which builds autonomous software testing for insurance carriers and insurtechs, starting with life insurance. He founded QA Consultants in 1994 and built it into one of the largest independent software testing firms in North America. When ALTEN acquired the firm in 2023, he carved out its emerging technology division, a team of PhDs and engineers building testing accelerators, and it became Emtech. He is the author of The Book on Testing and sits on LIMRA's Strategy and Innovation Committee. Key Topics -Who checks the AI's work - If AI tests code against the same understanding it used to write it, flawed code passes every test, so validation has to come from someone outside the build. -Testing is still mostly manual - The knowledge of how a carrier's systems behave sits in the heads of long-tenured testers, and Alex says manual coverage at most carriers lands around 10 to 20%. -The digital blueprint - Emtech maps a carrier's systems from the e-app through underwriting and policy admin to the issued policy, which Alex says adds up to hundreds of millions of test cases. -No AI in the testing - Emtech builds the blueprint from deterministic data and runs on-site on desktops, because most carriers won't expose their back end to an outside AI. -The enterprise AI licenses carriers aren't using - Alex argues that carrier AI is blind to the back end, and that giving it an accurate blueprint is what makes it useful, from user guides to product filings. -Regression across legacy and acquired systems - End-to-end regression covers mainframes, acquisitions and issued PDFs, and runs in parallel on testers' desktops in days instead of months. -The future QA team - Alex expects testers to become the stewards of AI inside carriers, because they are the people who understand the systems end to end. Notable Quotes "We need technology to test technology, but it cannot be the same technology." "The knowledge that people have in their heads is often not documented." "If you take that and you give that to the enterprise AI, that's the missing piece." "Testers need to become the stewards of AI enablement within organizations because they're the subject matter experts really understanding end-to-end." Resources Guest: Emtech Group: https://emtechgroup.com/ The Book on Testing: https://books.friesenpress.com/store/title/119734000184141596/Alex-Rodov-The-Book-on-Testing Alex Rodov on LinkedIn: https://www.linkedin.com/in/alexrodov/ Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast (LinkedIn Showcase): https://www.linkedin.com/showcase/insurtech-leadership-show Subscribe & Review If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Podbean, Apple Podcasts, and Spotify.

Introduction Insurers have spent two years funding AI pilots, and their boards are now asking what those pilots delivered. Why can so few carriers give a clear answer? Jim Quick leads the insurance advisory sector for PwC in the US, and PwC is four years into studying which companies get real value from AI. His finding is that carriers taking an incremental approach are seeing the least of it. The carriers getting the most picked their hardest problems, such as new business and underwriting or how fast claimants get paid, and rebuilt the whole process. Guest Bio Jim Quick is the Insurance Advisory Sector Leader at PwC US, where he oversees the firm's consulting platforms for insurers, including deals, AI, engineering, strategy, customer, and risk and regulatory work. He has spent about 25 years consulting to the insurance industry across personal and commercial P&C, life and annuities, and group benefits, and most of his direct client work today is in life and group benefits. PwC has more than 5,000 insurance-focused professionals in the US and more than 14,000 globally. Key Topics -Going big beats going incremental - Across PwC's AI performance study, the companies getting the most value attack their hardest problems, which Jim calls a culture and leadership challenge more than a technology one. -A practical sequence - Get hands-on with the tools, spend a couple of weeks rethinking the work, go after the toughest problem with leadership backing, and move to the next hardest problem if the first one doesn't work. -Growth over efficiency - Most of the market started with cost savings, while PwC's most innovative insurance clients are aiming AI at growth, including bundling products and answering quote requests faster. -Tokenomics - Some companies have watched AI savings get eaten by token and data center spend, and the real cost of deployment has become a C-suite question. -Agents on the org chart - Carriers are working out how to account for and manage AI agents, and whether AI engineering should sit in a central office or inside each business unit. -Build is back, and hardening is the scarce skill - Jim expects far more custom development on the hyperscalers and frontier models, and says the hard part is getting a pilot into production with token usage contained and an audit trail in place. -Finish the core - Carriers still need a modern, auditable policy, billing and claims core, so Jim's advice to anyone mid-implementation is to finish it and use AI to deliver it faster. Notable Quotes "It's really not a technology problem at its core. It is a cultural, it's a leadership, and it's the willingness to really reimagine and be willing to take risks." "I like to say we're kind of making underwriting fun again, or making underwriting underwriting again." "It's pretty easy to build things in a pilot environment. What's much harder is to actually get it into production, contain the token usage and harden the solution so that it's auditable." "If you haven't done it, I think you should. And if you're in it, finish it." Resources Guest: PwC US Insurance: https://www.pwc.com/us/en/industries/financial-services/insurance.html PwC, "Reinventing insurance: An industry beyond the tipping point": https://www.pwc.com/us/en/industries/financial-services/library/reinventing-insurance.html Jim Quick on LinkedIn: https://www.linkedin.com/in/jiquick/ Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast (LinkedIn Showcase): https://www.linkedin.com/showcase/insurtech-leadership-show Subscribe & Review If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Podbean, Apple Podcasts, and Spotify.

-Introduction What does a mid-sized brokerage have that it cannot actually use? A specialized book and the data behind it, and none of the underwriting, capital, filing, and admin machinery it would take to turn that book into a program it owns. The ten largest firms solved this by buying MGAs. Cole Riccardi built Authentic to rent that machinery to everyone else, and nine of the top ten retail brokerages now work with him on digital programs anyway. In this conversation he explains why he refuses to call Authentic a software company, what he got wrong in the first two years, and why he went after Main Street before he went after the hard market. Guest Bio Cole Riccardi founded Authentic in 2022 after five years at Aquiline Capital Partners, where he invested across the insurance value chain and became convinced that nobody was building affinity insurance programs at scale. He built the company with a co-founder and COO who spent fifteen years as an actuary at AmTrust and a CTO who came out of six years at Amazon, and the platform was architected as multi-carrier, multi-tenant, and multi-product from the first day. Authentic runs out of New York and Dayton, Ohio, is backed by FirstMark Capital, and now sits behind six carriers with programs spanning Main Street, energy, and inland marine. Key Topics -Programs should not be limited to the top ten - The largest brokerages own their own MGAs. Riccardi's argument is that everyone else already has the book and the data, and only lacks the machinery, which is a rentable problem. -An MGA that gives its software away - Riccardi is emphatic that Authentic never wanted to sell software and makes its money in the transaction flow. The technology is what makes it a better trading partner, not the product. -Affinity is product creation, not just distribution - For PushPress, Authentic went through the entire book and built four or five custom class codes that mapped to CrossFit gyms and similar facilities, rather than rating them off generic fitness codes. -Main Street first, on purpose - Rather than chase hard-market classes where premium comes fast, Authentic built a sizable Main Street book to prove that the configured programs were what moved business over, not market scarcity. -Same infrastructure, new practices - A Chubb energy underwriter joined with a thesis about independent power producers being underserved on casualty. That program launched in May, and an inland marine practice was announced the day of this recording. -The captive he overbuilt - Riccardi is direct that as a first-time founder he overcomplicated the early years by building custom captive cells on the back end. The captive still exists and takes smaller slices, but it is no longer the pitch. -Fast nos and the right to win - Authentic has no trucking underwriter and no capacity partner who will raise a hand for it, so brokers asking about long-haul trucking get turned down quickly rather than strung along. Notable Quotes "We never wanted to sell software. I always wanted to be in the transaction flow. We make money as an MGA today. That's always how we will make money." "Nine of the top ten work with us today on digital programs." "We've actually gone after Main Street to start and built up a pretty sizable book there. We wanted to do that so we could prove to ourselves that our technology mousetrap mattered and we weren't just writing business because it was hard to find markets elsewhere." "Can we challenge the status quo that MGAs need twelve points to operate? If you're built on modern systems, I don't think you do." Resources Guest: Authentic: https://authenticinsurance.com/ Authentic, For Brokers: https://authenticinsurance.com/brokers Cole Riccardi on LinkedIn: https://www.linkedin.com/in/cole-riccardi-63a243127/ Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast (LinkedIn Showcase): https://www.linkedin.com/showcase/insurtech-leadership-show Subscribe & Review If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Podbean, Apple Podcasts, and Spotify.

Introduction What is an insurer actually buying when it signs an AI contract? Dan Griffith's answer is that the failures came from companies buying AI because they needed AI, and the wins came from companies buying a migration that finishes faster at a fixed cost. Tim Vieyra runs Comotion AI, a Cape Town firm that spent twelve years building analytics and policy administration software other companies put their name on, and is now selling in the US under its own. Dan is advising Comotion on that entry, so this conversation runs two threads at once: what has to be true about an insurer's data before any AI project is real, and what has to be true about a company before it tries to sell into the American market. Guest Bios Tim Vieyra is a qualified actuary who left corporate financial services in 2013 to co-found Comotion, a software and data firm serving life insurance, investment, and healthcare clients. Comotion built the analytics engine behind TAI Insights and has worked with RGA South Africa. Comotion AI is the platform version of that work, putting governed, queryable structure over insurance, finance, and mortgage data, with data migration and profiling as the lead use case. Dan Griffith spent thirty years in enterprise sales, including a run as the first US hire for a South African company he helped scale from $3M to $150M, and now runs Greater Gain Group, which helps international software companies land and scale in US insurance and financial services. Key Topics -Buying an outcome, not AI - Griffith argues the failures came from companies that bought AI because they needed AI. What Comotion's customers buy is a migration that lands faster at a fixed acquisition cost. -Profiling in week one instead of month six - Vieyra explains that migration teams have historically found their data problems only after loading a target system and running reports. Comprehensive profiling on ingest moves that discovery to week one or two. -Governance resonated least - Griffith expected governance to carry the pitch and found it landed weakest, because governance is not a problem until it becomes one and the industry has not settled what the word means. -Narrowing the message on purpose - Vieyra describes shifting from "we can help with a broad array of problems" to two named use cases. That limits bandwidth, but it cuts through the noise faster. -South Africa versus the US - A smaller market rewards land-and-expand relationships and tolerates a muddier value proposition. The US demands a dialed-in problem statement and credibility, and then it opens up. -ICP first, everything else after - Griffith walks through the full-day workshop that set Comotion's ideal customer profile, and why a pilot should be priced as a percentage of the full deal and bounded by either time or scope. -Reset advice for stalled AI programs - Vieyra's answer for anyone whose AI initiative is not working is to re-evaluate the project against what the team knows now, not what it knew when the decision was made. Notable Quotes "Hold on to your paradigms loosely. Be humble enough to know that what you know now is not what you knew when you made the decision. And be willing to cut your losses and move to things that work." "We see failures all over the place because people just bought AI because they needed AI." "Governance isn't a problem until it's a problem." "In the US you have to have a much more dialed in and focused value proposition. You have to have a very, very clear problem that you're solving and credibility on why people should believe you. If you tick those boxes, the market is open to you." Resources Guests: Comotion AI: https://www.comotion.ai Comotion Business Solutions: https://www.comotion.us Tim Vieyra on LinkedIn: https://www.linkedin.com/in/timalive/ Greater Gain Group: https://www.greatergaingroup.com Dan Griffith on LinkedIn: https://www.linkedin.com/in/dangriffithsr/ Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast (LinkedIn Showcase): https://www.linkedin.com/showcase/insurtech-leadership-show Subscribe & Review If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Podbean, Apple Podcasts, and Spotify.

Introduction Why would an industry that governs almost everything still leave AI sitting on the back burner in the workflows where it would matter most? Earnix research puts AI in most or some workflows at 81% of insurers, and 92% of them run formal AI governance reviews, but fewer than one in three executives strongly agree those reviews are keeping pace with regulation. Aaron Wright, VP of Professional Services for the Americas at Earnix, spends his working life on the far side of that gap, and he argues it is not really a technology problem at all. In this episode, Josh Hollander and Aaron work through what separates transformation from transformation theater, why modernization programs tend to fail three months before go-live rather than at it, and where AI is already moving numbers a CFO would recognize. Guest Bio Aaron Wright is VP of Professional Services, Americas at Earnix, and a Fellow of the Casualty Actuarial Society. He started out of school with a statistics degree as an actuarial analyst at Farmers Insurance, and was on the phone with a Department of Insurance defending the math behind a rate change within six months. He then spent roughly twenty years at USAA across pricing, underwriting, state management, catastrophe management and data science, closing out with a modernization mandate. He now leads the teams that arrive after a carrier has bought the technology and someone has to make it actually work. Key Topics -The governance gap - Formal reviews are nearly universal, but the confidence that they track where regulation is heading is not, so real operational decisions move at a measured pace. -"We have AI" versus AI on the balance sheet - Aaron separates the places where AI is moving cost per ticket and handle time from the places where it is still hype. -Where programs actually fail - Not at go-live, but months earlier, when somebody has to kill a customization or force a business unit to change and nobody holds the authority to make that call. -The scaffolding problem - Carriers have built so many workarounds around legacy systems that the workarounds, not the systems, are often what hold them back. -Parallel-process fatigue - Running the old process alongside the new one creates burnout that can kill a project's momentum, and only leadership can set expectations around it. Vibe coding has a ceiling - Aaron will build a prototype to show the art of the possible, and he will not put it into a governed insurance environment. -AI that enables expertise - One Earnix customer sees about twelve months of average tenure in the call center against eighteen months to train a representative fully, which is the kind of math that makes embedded, governed AI worth the effort. Notable Quotes "Saying you have AI and actually having it be something that hits the balance sheet that your CFO cares about is a very different thing." "Most programs are not going to fail at the go live. They're going to fail three months before it, when somebody has to make that unpopular call and there's nobody with authority to actually make it happen." "The average tenure for call center representatives is about twelve months at their company, and it takes eighteen months to get them fully trained. Well, that doesn't work." "Our view of how AI should be used within insurance is to enable expertise." Resources Guest: Earnix: https://earnix.com/ Aaron Wright on LinkedIn: https://www.linkedin.com/in/aaron-wright-fcas/ Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast (LinkedIn Showcase): https://www.linkedin.com/showcase/insurtech-leadership-show Subscribe & Review If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Podbean, Apple Podcasts, and Spotify.

Introduction Ask an insurance operator to write down how a policy endorsement actually gets processed, and you will usually get about six steps. The real number is closer to fifty. The other forty-four live in the head of whoever has been doing the job longest, and they leave when that person does. Giancarlo Stanton, Co-Founder and CEO of Magiq, has built a company around that gap. His argument is that you have to know what the process actually is before you automate it, and most operations don't. The industry is buying agents to handle work nobody has written down, which is how you end up with a system whose decisions nobody can explain. In this episode, Josh Hollander and Giancarlo get into what it takes to pull a process out of a competent person's head, why the exceptions matter more than the normal path, and what changed in one support operation once someone finally mapped the work. Guest Bio Giancarlo Stanton is Co-Founder and CEO of Magiq. He started in complex commercial litigation, moved in-house, and became General Counsel and VP of Claims at Swyfft before serving as Chief Operating Officer at Cover Whale. Along the way he advised Obie, FRG Specialty, and Sunfish. That path put him in the back office of regulated businesses during periods of fast growth, which is where he formed the view that the minutiae are the whole game. He founded Magiq with Nick Eich, previously at Groupon and then on the engineering team at Kin, to build the thing he kept needing as an operator: a way to go from what should get done to proof that it actually happened. Key Topics -Your best people cannot describe their own jobs - When something becomes routine it becomes invisible, so asking an expert to write down what they do all day produces a partial answer at best. -The mirror problem - Magiq shows an organization its own process as steps one through fifty, and the response is almost always that leadership knew about step one and step fifty and assumed the rest. -Insurance runs as an ecosystem, not as silos - When billing misses a cancellation for nonpayment, claims pays a loss that should never have existed, which is why Giancarlo argues point solutions aimed at one function cannot fix the operation. -The exceptions are where the value sits - The flat cancel and rewrite that one person handles differently today than yesterday is what turns a bordereau into a conversation with your reinsurer about why the math doesn't math. -What mapping the work actually did - A support operation went from a one-in-five call response rate and an 8.8 day email response time to 96-97% call response and 5.8 hours, seven months in. -Sales is a process too - Mapping the inbound lead decision tree and empowering producers to end calls that were never a fit drove a 23% improvement in per-producer output and a $10 million gross written premium lift over a seven month engagement. -The staffing question - Giancarlo makes the case that doing more with the team you have lands better with buyers than headcount reduction, and that a business only profitable with no employees was never really profitable. Notable Quotes "You can't automate things you don't understand. And that, I think, is just objectively true. But that doesn't stop people from trying." "No one is sitting there running a business saying, I need more AI. They're saying, I need less cost, or I need more sales, or ideally both. And probably fewer errors." "People don't do things incorrectly because they want to. They do things incorrectly or inefficiently because they think they're doing them correctly, but it's eight thirty at night and it's their fiftieth endorsement." "If the only way your business is profitable is for there to be no employees, then you probably just don't have a profitable business to begin with." "It's really about making sure the mistakes don't happen, not making sure the people aren't there." Resources Guest: Magiq: https://usemagiq.com/ Giancarlo Stanton on LinkedIn: https://www.linkedin.com/in/giancarlo-stanton-1b011a59/ Magiq on LinkedIn: https://www.linkedin.com/company/usemagiq Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast (LinkedIn Showcase): https://www.linkedin.com/showcase/insurtech-leadership-show Subscribe & Review If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Podbean, Apple Podcasts, and Spotify.

Introduction What does an insurer actually own after a few years of buying AI one use case at a time? Feathery co-founder Zack Khan argues that the answer decides whether AI ever produces more than incremental gains, because a workflow you cannot change without filing a vendor ticket is a workflow you are renting. Fresh off a $30 million round led by Portage, with Allstate and Erie both in as strategic investors, Khan walks host Joshua R. Hollander through what it takes to put workflow control in the hands of the operating teams themselves. Guest Bio Zack Khan is Co-Founder of Feathery, the AI operating and decisioning system for financial services. He started as a software engineer building complex forms at Robinhood and Nextdoor alongside co-founder Peter Dun, then became the fifth employee at Hightouch, where he led marketing as the company grew toward a $3 billion valuation. Khan and Dun founded Feathery in 2021 as a developer-focused form builder and grew it into a platform that now serves more than 300 firms, including Tokio Marine, Hiscox, Baldwin Group, and Hylant, orchestrating submission intake, virtual inspections, quoting, and benefits workflows across carriers, MGAs, and brokers. Feathery ran profitably before raising its $30 million round in July 2026. Key Topics -Vendor-led vs. team-owned workflows - Why the last generation of insurance software put every change behind a vendor ticket, and what changes when underwriting and operations teams define workflows in natural language instead. -Copilot licenses vs. step changes - Giving everyone a copilot produces small gains; redefining one workflow end to end took a carrier from an eight-hour time to quote down to fifteen minutes. -Orchestrate rather than replace - Feathery's agent, Robin, works across existing rating engines, AMSs, and even legacy desktop applications, automating the data entry instead of ripping out the system. -Rules where you want them, judgment where you need it - Deterministic guardrails handle rating inputs, while objective-driven agents handle tasks like checking a virtual inspection for a pool or a tree touching the roof. -The Baldwin Group benefits example - Custom employee benefit guides that took 20 to 30 or more hours to build now generate in minutes, across 10 to 15 assets and multiple languages, and the team's hours moved to consultative work. -What a platform actually is - Khan's test is control: if you cannot apply your own business logic to your own workflow without a vendor ticket, you bought a point solution. -Start in specialty lines - Fast-growing lines with less tech debt and less red tape are where AI transformation finds its first champions inside a large carrier. Notable Quotes "An actual platform gives you control. If you don't have fundamental control over the actual experience, and you're applying your own firm-specific business logic to your workflow, that is a point solution." "If your rating engine is working great, it's just the annoying part is typing data into it. You don't rip out the whole rating engine; you just automate the data entry part of it." "Some of our customers have gone from an eight-hour time to quote to less than fifteen minutes responding to producers. That's the stuff that actually will impact your bind ratio." "For AI to truly have the impact you want, you need to redefine the workflow, think about the end-to-end ideal process that you want your best underwriter, your best claims adjuster, your best producer to be following." Resources Guest: Feathery: https://www.feathery.io/ Zack Khan on LinkedIn: https://www.linkedin.com/in/zackkhan101/ Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast (LinkedIn Showcase): https://www.linkedin.com/showcase/insurtech-leadership-show Subscribe & Review If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Podbean, Apple Podcasts, and Spotify.