Full Episodes | Insurtech Leadership Podcast

Reinventing the Broker Experience: Tech, Trust, and the Future of Personal Lines

Introduction

What if the biggest gap in personal lines insurance technology isn't the consumer experience—it's the broker experience? Every major insurtech wave of the past decade has tried to disintermediate the agent. Jon Kelly thinks that's the wrong bet. In his view, the broker is the product in personal lines, and the tools they work with are embarrassingly behind.

Kelly has been building at the intersection of insurance and technology since 1998, when he co-founded eCoverage—the first venture-backed startup to underwrite car insurance online. After selling SureHits in 2008, he spent years watching high-net-worth clients get onboarded with hundreds of questions spread across weeks of back-and-forth, proposals built in Excel, and data managed across disconnected systems. He called it "the Columbo experience"—always just one more thing. That frustration led him to co-found Kelly Klee Private Insurance in 2016 and build Discover, the platform powering it, from the inside out. Kelly Klee was acquired by Foundation Risk Partners in 2022. Now, as CEO of Modern Metric, he's selling Discover to the largest national brokers in the country.

In this conversation, Josh Hollander and Kelly dig into the technology gap in personal lines, why enterprise-first was the right strategic bet, what it takes to hire high-agency people, and why trust is the ultimate product in this business.

Guest Bio

Jon Kelly is the Founder and CEO of Modern Metric, makers of the Discover platform for personal lines insurance distribution. His career began in 1995 at Mercer Management Consulting, advising Prudential, CNA, and Fireman's Fund. In 1998 he co-founded eCoverage, the first venture-backed startup to underwrite car insurance online, followed by SureHits (acquired by QuinStreet, 2008) and Kelly Klee Private Insurance (acquired by Foundation Risk Partners, 2022). He chairs Hometown Quotes, sits on the board of Great Range Capital, and earned a BA in Economics and Political Science from Stanford University.

Key Topics

• The missing layer in the tech stack — Independent agents have AMS systems for back-office accounting, CRMs for lead tracking, and form builders as pipes to carriers. But there is no purpose-built system for the client-facing workflow: data discovery, market presentation, and proposal delivery. That gap is what Discover was built to fill.

• Relationship business vs. transactional business — The real split in personal lines isn't private client vs. mass market—it's relationship (multi-line) vs. transactional (monoline). Form builders work fine for monoline. They fall apart the moment complexity enters the picture.

• Enterprise-first as a strategic decision — The most consequential decision at Modern Metric was targeting the largest national brokers from day one. Building for complex, enterprise-scale accounts forces architectural decisions that cannot be retrofitted later. You can scale down from enterprise; you cannot scale up from a form builder. Their first anchor tenant is a top-20 national broker.

• The Uber Black analogy — If you order an Uber X and the Uber Black shows up, you're thrilled. If you order the Uber Black and the old Honda arrives, you're not happy. A platform built for simple transactions will never feel right in a complex private client context, no matter how much you add to it.

• Hiring for high agency — The through line across all of Kelly's businesses: he hires for high agency. He looks for people who have clear motivations for every role on their resume. His favorite interview story: asking a candidate about their favorite exhibit at the natural history museum where they worked. The answer was "that was okay." They didn't get the job.

• Trust as the ultimate product — Kelly's answer to what he'd want co-founders, teammates, and customers to say: that he delivered on what he said he would, that they got good value, and above all, that they can trust him. Trust is number one.

Notable Quotes

"I called it the Columbo because it was always just one more thing. Oh, your house is in a trust? Just one more question. I couldn't help think that maybe there were some issues with technology and personal lines, especially at the high end."

"The whole process of how do you get the data in, how do you take that to market, how do you do your proposal—that's all done in paper and pencil, Excel and Word and Outlook."

"If you order an Uber X and the Uber Black comes, you're thrilled. If you order Uber Black and the old Honda comes, you're not happy. You can't go from one to the other."

"What I'd want them to say is that I delivered-that whatever I said I was going to do, I did, and that they got value out of it. More than anything, that they feel like they can trust me. Trust is number one."

Resources

Guest:
• Modern Metric: https://www.modernmetric.com
• Jon Kelly on LinkedIn: https://www.linkedin.com/in/jonkelly/

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

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Rebuilding Underwriting From the Inside Out: The AI OS for Modern MGAs

Introduction

What if the real bottleneck in commercial insurance isn't distribution or pricing—it's the workflow itself? Nearly $100 billion of SME P&C insurance is placed every year using manual processes, disconnected systems, and data that lives in spreadsheets and email threads. Hamesh Chawla has spent the last four years building the infrastructure to change that.

Before founding Mulberri in 2021, Chawla led product and technology at Edelman Financial Engines and Asurion. He came to insurance not as a lifer but as a technologist who saw an industry still running on 20th-century tooling. Mulberri is his answer: an AI operations platform connecting PEOs, brokers, SMEs, and carriers—from smart submission and risk scoring to quote-and-bind and certificate of insurance.

In this conversation, Josh Hollander and Chawla dig into why the MGA market was the right pivot, what AI governance looks like when binding decisions carry real capital risk, and why the SME segment is the most underserved frontier in commercial insurance.

Guest Bio

Hamesh Chawla is the Co-Founder and CEO of Mulberri, an AI operations platform for MGAs, PEOs, brokers, and carriers serving the SME market. Before Mulberri, he was EVP and Chief Product & Technology Officer at Edelman Financial Engines, with prior roles at Asurion and Zephyr (acquired by SmartBear). He holds an MS in Computer Science from Texas A&M University. Mulberri has raised $10.8M from Eos Venture Partners, Altamont Capital Partners, MS&AD Ventures, and Hanover Technology Management.

Key Topics

• The $100B manual workflow problem — Nearly $100B of SME P&C is placed annually using ACORD forms emailed back and forth, loss runs parsed by hand, and decisions made without the data that exists in the market. Mulberri automates this stack.

• From embedded insurance to AI operating system — Chawla explains why he pivoted from embedded distribution to building the workflow layer MGAs actually run on—ingesting unstructured data, structuring it through a GenAI OS, and routing decisions with full context.

• AI governance when capital is at stake — When AI is binding real policies, black-box models get rejected. Mulberri surfaces claim propensity, frequency, severity, and loss ratio so underwriters can interrogate and trust the output.

• The PEO channel as data and distribution — PEOs sit on firmographic and workforce data directly predictive of workers' comp risk. Embedding into that channel is both a data strategy and a go-to-market strategy.

• Building for carriers, brokers, and SMEs simultaneously — Carriers need loss ratio visibility, brokers need submission efficiency, SMEs need straightforward access. Aligning all three is the hardest product problem in the space.

Notable Quotes

"Our mission since day one has been to leverage technology to complement underwriters' expertise—simplifying and streamlining the business insurance process while ensuring transparency."

"The Risk Engine puts the information underwriters need at their fingertips to make fast, accurate decisions—not replacing them, but making them dramatically more effective."

Resources

Guest:

• Mulberri: https://www.mulberri.io

• Hamesh Chawla on LinkedIn: https://www.linkedin.com/in/hameshchawla/

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

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Why Nobody Is Scoring the Road Ahead (And What It’s Costing Insurers)

Introduction

What if the most dangerous thing about a commercial fleet route could be identified before the truck ever left the yard? The insurance industry has spent decades pricing commercial auto risk using historical loss data and, more recently, real-time telematics. But neither tells you what's waiting around the next bend. The forward-looking layer has never existed.

Goetz Weber is a theoretical physicist turned mapping executive turned insurtech founder. After a decade at TomTom and HERE Technologies optimizing routes for time and distance, he asked a different question: why isn't anyone optimizing for risk? RouteRisk.ai is his answer. The company scores every commercial route across sixty-plus variables before dispatch, producing what Weber calls "a FICO score for fleet routes."

In this conversation, Josh Hollander and Weber dig into the science behind segment-level route scoring, the insurance market's fourteen-year losing streak on commercial auto, and why giving the technology away for free might be the smartest distribution strategy in fleet insurtech.

Guest Bio

Goetz Weber holds a PhD in quantum field theory and spent over a decade in the navigation and mapping industry, serving as VP of Innovation at TomTom and previously at HERE Technologies. In those roles, he worked directly with fleet operators, fleet management companies, and logistics platforms. He founded RouteRisk.ai to address a gap he identified firsthand: routing companies optimize for cost, time, and distance, but nobody scores risk. RouteRisk is now Series A funded, integrating with platforms like Samsara, and building its go-to-market for insurance distribution.

Key Topics

• The missing layer in fleet risk assessment - Historical data looks backward, telematics looks at the present, but nobody scores what's about to happen. RouteRisk fills the forward-looking gap with pre-dispatch route scoring.

• Sixty-plus variables in a single route score - Static road geometry, forward weather, traffic predictions, vehicle physics, cargo sensitivity, theft corridors, and incident history, all scored at the segment level and aggregated with interaction effects.

• The FICO analogy for fleet routes - A composite risk score that tells dispatchers, fleet operators, and insurers the risk profile of a specific route, at a specific time, for a specific vehicle carrying specific cargo.

• Risk appetite as underwriting data - When a fleet operator chooses a route scored at 80 over one scored at 40, that decision is captured. Over time, this builds a behavioral profile of risk appetite that insurers have never had access to.

• Free-to-fleet, monetize-through-insurance - RouteRisk gives the scoring tool to fleet operators at no cost (reducing their accidents and insurance leverage) and sells the risk decision data to carriers and reinsurers.

• Three paths to insurance market entry - Form a proprietary MGA, partner with existing fleet insurers on incentive-based pricing, or go directly to reinsurers who bear nuclear verdict risk.

• Why this isn't the telematics adoption problem - Telematics monitors drivers (creating resistance). RouteRisk scores roads and empowers dispatchers. No cameras, no surveillance, no cost barrier.

Notable Quotes

"I think of vehicles moving through space as moving through risk fields, dynamic risk fields that come and go, whether it's weather, traffic, road conditions, theft hotspots."

"If I show you two routes and one has a risk score of forty and one has a risk score of eighty, and you choose the eighty, I've captured your risk appetite. And that data is gold for an insurer."

"If you and I both go to a ski resort, but you do extreme downhill and I do cross-country, technically we should have different insurance programs. Our data reveals which fleet operators are the extreme downhillers and which are the cross-country skiers."

"Risk should be visible and manageable before it materializes, not just measured after it has."

Resources

Guest:

• RouteRisk.ai: https://www.routerisk.ai

• Goetz Weber on LinkedIn: https://www.linkedin.com/in/goetzweber/

Host:

• 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

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From Travelers Executive to AI Startup: What’s Harder, What’s Easier

Introduction

What happens when a decade-long carrier executive decides that the best way to fix insurance operations is to stop advising from the inside and start building from the outside?

Vijay Laknidhi spent his career at Travelers and Amtrust, sitting in the rooms where technology decisions stalled, procurement cycles stretched past usefulness, and AI pilots died in committee. Now, as GM of Commercial Insurance at Liberate, a voice AI company built exclusively for P&C, he runs what he calls "a Series A company inside a Series B company," tasked with scaling a P&L dramatically in a single year.

In this episode of the Insurtech Leadership Podcast, host Joshua Hollander sits down with Vijay to unpack what it actually looks like to cross from buyer to builder, why commercial insurance is uniquely ripe for AI disruption, and what separates production-grade insurance AI from a compelling demo.

Guest Bio

Vijay Laknidhi is the General Manager of Commercial Insurance at Liberate, a voice AI company focused exclusively on property and casualty insurance. Before joining Liberate, Vijay spent over a decade in executive roles at Travelers and Amtrust, where he led underwriting, product, and operational functions across commercial lines. His carrier-side experience gives him rare dual fluency: he understands the internal politics, compliance requirements, and procurement friction that slow AI adoption at large insurers, and he now builds the products designed to break through those barriers. At Liberate, he operates with startup autonomy and carrier-grade expectations.

Key Topics

• The carrier-to-startup leap - Why a successful insurance executive would leave the stability of a Top 10 carrier to join a Series B startup, and what that transition actually demands

• Voice AI in P&C operations - How Liberate applies voice AI to claims intake, FNOL, and policy servicing, replacing legacy IVR and manual call center workflows

• Why commercial insurance is the AI beachhead - The structural reasons (submission volume, manual underwriting, broker friction) that make commercial lines more amenable to AI than personal lines

• The demo-to-production gap - What separates an impressive AI proof-of-concept from a system that handles edge cases, compliance, and carrier-grade uptime in production

• Selling to the buyers you used to be - How Vijay's decade on the carrier side shapes his approach to navigating procurement, legal review, and stakeholder alignment at prospect companies

• Why every insurance leader must get hands-on with AI - The argument against delegating AI strategy to innovation teams or consultants, and why executives need direct fluency

• AI-native architecture vs. legacy tech debt - Why recent startups like Liberate have a structural advantage over incumbents trying to bolt AI onto decades-old policy admin systems

Notable Quotes

-"I'm running a Series A company inside a Series B company. I own the P&L, I own the roadmap, and I have one year to prove the commercial insurance thesis."

-"When you've sat in the buyer's chair for a decade, you know exactly which objections are real and which ones are just procurement theater."

-"The gap between an AI demo and a production deployment in insurance is compliance, edge cases, and the willingness to handle the 2% of calls that don't fit a script."

-"If you're a carrier executive delegating AI to your innovation team, you've already lost. You need hands-on fluency, not a briefing deck."

Resources

Guest:

• Liberate: https://www.liberatetech.ai/

• Vijay Laknidhi on LinkedIn: https://www.linkedin.com/in/vijaylaknidhi/

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

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If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Apple Podcasts, and Spotify.

Special Virtual Episode: Applied Systems and the Digital Round Trip

Introduction

What happens when the insurance industry's dominant agency management platform decides manual data entry is no longer acceptable? Applied Systems is betting its product roadmap on a three-ring strategy they call the "digital round trip," combining embedded AI, strategic acquisitions, and platform overhauls to eliminate the operational drag that costs agencies thousands of hours per year. This deep dive unpacks the core strategy shifts, the specific technologies driving change, and the leadership decisions behind a platform serving 37,000 agencies and 300,000 users.

Key Topics

• The Digital Round Trip Framework - Applied's three concentric rings: core agency management (Epic), carrier collaboration (Ivans, Cytora), and embedded AI. Each ring represents a strategic investment layer aimed at turning Epic from a system of record into a system of action.
• Cytora Acquisition and Zero-Training AI - How Cytora's "agentic team" of seven LLMs running at different temperature settings extracts structured data from unstructured inputs (emails, PDFs, voice calls) without pre-labeled training data, cutting submission prep from hours to minutes.
• Epic AutoFill for Benefits and Commercial Lines - AI-powered extraction that reads SBC documents and complex vehicle schedules in seconds, saving an estimated 30 minutes per plan and 2-3 hours per commercial submission in manual data entry.
• Epic Max: The Natural Language Copilot - Applied's AI assistant targeting the 2-3 hours per day agency staff spend searching for information. Goal: recapture 12,000 hours (equivalent to 6 FTEs) in its first year through instant natural language queries with auditable source chains.
• BPO Disruption - Applied's aggressive stance that AI should replace outsourced data entry, directly challenging the business model of agencies spending $500K+ annually on BPO for routine tasks.
• Agency Valuation and M&A Implications - How AI adoption and system consolidation make agencies more attractive to acquirers. Clean data, lower operating costs, and standardized workflows command premium multiples.

Notable Quotes

"Their strategy comes from clients saying, we're spending way too much money outsourcing stuff that the software should just do."

"The initial fear of AI seems to be turning into FOMO on AI. Because if your competitor is saving 2 hours per person per day, you literally can't afford not to adopt."

"An agency that uses this tech to streamline workflows, clean up its data, lower operating costs becomes way more attractive to buyers. It's the after photo."

"Automating the simple decisions is becoming table stakes. Using AI to master the triage and routing of the most complex risks to the human brain might be the real competitive advantage in the next decade of insurtech."

Resources

Applied Systems:

• Applied Systems: https://www.appliedsystems.com/
• AppliedNet Conference: https://www.appliednet.com/

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.

Beyond Wildfire: How Jessica Leong and Octagram Analytics Are Rethinking Fire Risk in Insurance

Introduction

In this episode of the Insurtech Leadership Podcast, host Josh Hollander welcomes back Jessica Leong, co-founder of Octagram Analytics, to discuss FireRQ — a non-catastrophe fire risk model delivering actionable risk scores for any U.S. address. While the industry fixates on headline-grabbing catastrophes, Jessica and her team are tackling the everyday fire risk that quietly drives loss ratios, underwriting decisions, and portfolio performance.

Guest Bio

Jessica Leong is co-founder of Octagram Analytics, an actuarial analytics firm. Before founding Octagram, she served as Head of Data & Analytics at Zurich North America, where she led the team that built all predictive models for pricing and claims. She is also a former President of the Casualty Actuarial Society. Jessica brings over a decade of experience in insurance predictive analytics to the problem of non-catastrophe fire risk.

Key Topics

• Non-cat fire risk: the overlooked loss driver — Fire (excluding wildfire) accounts for 15–30 points of property loss ratio in homeowners and commercial lines, yet most carriers treat it as a solved problem. Jessica explains why it isn't.
• The dataset advantage: 1.7 million fires — Octagram built FireRQ on the National Fire Incident Reporting System (NFIRS), a publicly available dataset of fires reported by U.S. fire departments. Even Fortune 500 carriers only see ~1% of this data in their own books.
• Repeat fires and fire clusters — The data reveals that buildings with prior fires are significantly more likely to burn again, and that fires cluster by geography and occupancy type. The Myrtle Beach hotel cluster (10–15 hotel fires per year in a single zip code) is a striking example.
• Machine learning for fire prediction — FireRQ uses a gradient boosting machine (GBM) that starts with building-level history, then branches outward to area and occupancy-level fire experience. The model captures 80% of fires in the worst 20% of buildings.
• How underwriters use FireRQ — Carriers apply the score for pricing adjustments, risk selection (declining high-score accounts), and early warning. Octagram offers a free proof of concept using an older model version so clients can validate on their own loss data.
• Model transparency and explainability — As larger accounts adopt FireRQ, demand for "why" behind scores is growing. Octagram is adding context layers: prior fires at the location, area-level fire frequency, occupancy benchmarks.
• What's next for Octagram — LiabilityRQ and CrashRQ are in development, extending the same data-driven approach to liability and auto crash risk.

Quotes

• "We can look at 100% of the data where you're staring at 1% of the data."
• "If we tell you these buildings are the worst 20% buildings in the U.S., we do see they have 80% of the fires."
• "No one talks about [non-cat fire] anymore, but it's still a very, very real risk."

Resources

• Octagram Analytics website: octogramanalytics.com
• The Little Book of Fires: Free resource available on the Octagram Analytics website
• National Fire Incident Reporting System (NFIRS): Publicly available U.S. fire data

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From Ultramarathons to Market Shifts: Scott Sambucci on Leading Innovation

Introduction

What happens when a bank finds the right technology but can't touch it for nine months? The procurement bottleneck in regulated financial services isn't just an inconvenience. It's a competitive disadvantage measured in quarters, lost sponsors, and dead deals.

Scott Sambucci, Managing Director of North America and Europe at NayaOne, has spent 25 years selling into and building technology for financial institutions, from CoreLogic to Blend Labs. Now he's leading the US and Canadian expansion of NayaOne's sandbox-as-a-service platform, the same infrastructure the UK's Financial Conduct Authority chose to power its own digital sandbox. In this episode, Scott breaks down why the vendor delivery problem is the real blocker to innovation in insurance and banking, and how air-gapped sandbox environments compress proof-of-concept timelines from months to weeks.

Guest Bio

Scott Sambucci is Managing Director of North America and Europe at NayaOne, where he leads market expansion for the London-based sandbox platform. Before joining NayaOne full-time in January 2024, he spent 25 years in Silicon Valley building and scaling technology companies in financial services, including executive roles at CoreLogic and Blend Labs. Scott is also founder of SalesQualia, a sales coaching firm, and teaches Sales & Marketing at Hult International Business School. A 200-mile ultramarathon finisher, he applies the same relentless-forward-progress mindset to enterprise sales and team building.

Key Topics

• The vendor delivery infrastructure gap — Banks and carriers need 6-12 months of third-party risk management, security, and compliance review before they can even pilot new technology, leaving them perpetually behind nimble competitors.
• How air-gapped sandboxes collapse procurement timelines — NayaOne's off-estate digital sandbox lets institutions run proof of concepts in weeks because the environment is completely separated from production systems, eliminating the need for individual vendor security reviews.
• The "vet once, test many" model — Once a bank approves NayaOne as a vendor, any future technology (from Y Combinator startups to CrowdStrike) can be tested inside the sandbox without repeating the TPRM process.
• Insurance-specific use cases: claims modernization — P&C carriers are using the platform to test AI-driven FNOL triage, claims routing, fraud detection, and payment automation across the full claims lifecycle.
• Multi-LLM side-by-side assessments — Banks are running comparative evaluations of ChatGPT, Gemini, and other LLMs inside the sandbox, the only way regulated institutions can safely touch these systems before committing.
• Integration testing with core systems — The platform replicates Guidewire, Duck Creek, Salesforce, and ServiceNow environments so carriers can validate interoperability before making a purchasing decision.
• Relentless forward progress as a leadership framework — Scott draws a direct line from 200-mile ultramarathons to building a US operation from scratch: plan station to station, leverage the team, and own everything that happens.

Notable Quotes

"What you've built here is a utility that every financial institution is going to need, whether they know it or not right now." — Scott Sambucci, Managing Director, NayaOne

"There's nothing more frustrating than making good progress with your sales demo, having good early conversations, but then being told it's just gonna take nine months for you to fill out all this paperwork." — Scott Sambucci

"By nature, every bank out there is going to be twelve months behind their competitive landscape because those competitors don't have those same guardrails yet." — Scott Sambucci

"No one's coming to help you. No one can pick you up and take you to the finish line. It doesn't matter how good or bad you feel — you just have to keep moving." — Scott Sambucci

Resources

Guest:

• NayaOne: https://nayaone.com/
• Scott Sambucci on LinkedIn: https://www.linkedin.com/in/scottsambucci/

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.

There’s Never Been a Better Time to Build in Insurance

How is private equity approaching the insurance technology opportunity differently than traditional venture capital? What happens when risk capital wants to move upstream in the value chain, and AI enables it to actually get there?

Guest

Joe Zuk is an Operating Partner at Altamont Capital Partners, where he leads corporate and business development across a portfolio of insurance and insurance services companies. With 23 years of industry experience, Joe spent 10 years as a reinsurance broker and underwriter, then 8 years with two MGAs building P&C verticals and corporate development functions. At Altamont, he oversees portfolio companies including Accelerant Holdings, Augment Risk, Embark General, Fleming Holdings, Ascendex Underwriters, Kuvare Holdings, and Hadron Holdings.

Key Topics

The Insurance Stack is Compressing - Risk capital (reinsurers, ILS, carriers) is moving upstream toward origination. Traditional 8-layer distribution is collapsing into 3: origination, translation, risk capital. AI is the enabler, but relationships still matter.

AI Solves Operational, Not Structural, Problems - The industry went through shiny object syndrome with AI. Real ROI comes from mundane efficiency: submission triage, claims processing speed, underwriting augmentation from unstructured data. Not flashy, but measurable.

Why PE Beats VC for Insurance - Insurance requires patience, regulatory expertise, and operational discipline. VC timelines are destructive. PE operating partners understand the regulatory cadence and can navigate it competently.

The Founding Team Playbook Has Changed - Today's insurance startups need a CTO or head of data as a founding hire, not just an underwriter and a producer. Talent comes from adjacent industries (fintech, healthtech) not just insurance veterans.

Now Is the Best Time to Build - Technology maturity, available talent, incumbent inefficiency, and collapsed barriers to entry mean founders can build insurtech companies that compete on quality and speed with much larger organizations.

Hiring for Curiosity Over Credentials - Altamont prioritizes intellectual curiosity and adaptability, especially for tech-forward roles. Domain expertise still matters, but learning velocity matters more.

Trust Cannot Be Automated - AI compresses workflows, but it doesn't compress trust. Relationships, sales, and concierge service remain core differentiators in insurance, even as the stack contracts.

Notable Quotes

"AI can compress workflows, but it doesn't compress trust."

"The insurance stack is compressing from eight layers down to three: origination, translation, and risk capital."

"We went through a period of shiny object syndrome with AI. The real ROI is in the mundane operational efficiency."

"I believe there's never been a better time to be an entrepreneur in the insurance market."

Resources

• Altamont Capital Partners: https://altamontcapital.com/

• Joe Zuk: https://joezuk.com/

• Follow Joe: https://www.linkedin.com/in/joezuk/

• Horton International: https://www.horton-usa.com/

Subscribe & Review

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#InsurTech #Insurance #InsuranceInnovation #Leadership #ExecutiveLeadership

The Retention Gap: Why Carriers Lose Policyholders They Priced Correctly

Introduction

What happens when carriers can predict where risk exists but have zero control over how that risk changes after the policy is written? Valkyrie Holmes, CEO and Co-Founder of Faura, returns to the Insurtech Leadership Podcast to answer that question with a new playbook: turn policyholders into active risk managers, and retention follows.

In this episode, Holmes unpacks Faura's retention engine for high-risk consumers, the two-page resilience report reshaping how homeowners engage with their own property risk, and why MGAs have become her favorite distribution partners. The conversation covers carrier trust, first-party data strategies, composable platform architecture, and what it takes to lead a scaling insurtech as the youngest person in every room.

Guest Bio

Valkyrie Holmes is the CEO and Co-Founder of Faura, a climate risk intelligence platform that evaluates property survivability across all five NATCAT perils: wildfire, hurricane, hail, flood, and earthquake. Holmes skipped college, interned at NASA and SpaceX, and co-founded Faura in 2023. The company has raised $3.5M in seed funding from Harlem Capital, Building Ventures, MetaProp, and Dorm Room Fund, won the State Farm Pitch Competition at InsureTech Connect, and secured a strategic partnership with Insurity to embed resilience analytics into P&C underwriting workflows.

Key Topics

• The Retention Engine - Faura's new approach to turning policyholders from passive premium-payers into active risk managers through engagement and behavioral data

• Two-Page Resilience Reports - Homeowner-facing reports that prioritize easy action items first, building momentum before introducing harder mitigation steps

• QR Codes and CA Compliance - How carriers use Faura's walkthrough module as a compliance tool for state-mandated wildfire discounts in California

• First-Party Property Data - Filling modifier gaps in carrier datasets by partnering with homeowners for ongoing risk information in exchange for incentives

• MGA Strategy - Why MGAs move faster, require less consensus, and have become Faura's ideal distribution partners over tier-one carriers

• Composable Platform Architecture - Building a system flexible enough to customize endpoints, reports, and fields for any carrier, broker, or distribution partner

• Differentiation in High-Risk Markets - What carriers need beyond price to retain policyholders as competition increases in FL, CA, and emerging catastrophe zones

Notable Quotes

"Historically, many carriers have been very good at predicting where risk exists, but have very little control over how that risk changes after the policy is written."

• Valkyrie Holmes, CEO/Co-Founder, Faura

"If you're re-entering a market or trying to take up market share, what is the reason someone stays with you over switching to another carrier for a fifty-dollar premium reduction next year?"

• Valkyrie Holmes

"Talk to everyone. Talk widely. And then narrow to your mission."

• Valkyrie Holmes

Resources

Guest:

• Faura: https://www.faura.us/

• Valkyrie Holmes on LinkedIn: https://www.linkedin.com/in/valkyrieholmes/

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.

Stop Mailing Checks: How Card-Based Payouts Are Reshaping Claims

Introduction

What if the biggest friction point in insurance isn't underwriting or distribution, but the moment a policyholder actually gets paid? For an industry built on the promise of financial protection, the claims payout process remains stubbornly analog, slow, and vulnerable to fraud.

In this episode of the Insurtech Leadership Podcast, host Joshua Hollander sits down with Andrew Jernigan, Head of Insurance, North America at Pliant, to dissect how card-based payout infrastructure is reshaping claims operations. From single-use virtual cards that eliminate fraud vectors to tokenized wallet payouts that meet policyholders where they already transact, Jernigan makes the case that modernizing the last mile of claims isn't just an ops upgrade, it's a revenue strategy.

Guest Bio

Andrew Jernigan is the Head of Insurance, North America at Pliant, a card-as-a-service platform modernizing claims and benefit payouts for insurers and payers. Prior to Pliant, he was the founder and CEO of Insured Nomads, a company built to serve globally mobile professionals with embedded insurance and financial wellness products. Jernigan brings a rare combination of carrier-side operating experience and fintech product instincts to the claims payout problem.

Key Topics

• Card-Based Claims Payouts - How single-use and virtual cards replace checks and ACH transfers, reducing settlement time from days to seconds

• Fraud Reduction Through Card Infrastructure - Why single-use cards with merchant category restrictions eliminate common payout fraud vectors

• Interchange as a Revenue Lever - The economics of card-based payouts: insurers can generate interchange revenue while reducing operational costs

• Tokenized Wallet Payouts - The near-term future where claims land directly in Apple Pay or Google Wallet, removing the need for physical cards entirely

• Branded Payout Experience - How carrier-branded payment cards turn the claims moment into a customer experience and retention touchpoint

• Implementation Simplicity - Why modern card-as-a-service platforms can integrate in weeks rather than the months-long cycles of legacy payment systems

• Communication as Retention Strategy - The hidden cost of poor claims communication and why payout speed alone doesn't solve the customer experience gap

Notable Quotes

"Use other people's money. That's literally the best advice in payments."

• Andrew Jernigan, Head of Insurance, North America, Pliant

"People are tired of believing that insurance is going to be like pulling teeth. They're waiting for innovation to happen."

• Andrew Jernigan

"It's not just speed. It's control. A single-use card means the money can only go where it's supposed to go."

• Andrew Jernigan

Resources

Guest:

• Pliant: https://www.pliant.io/

• Andrew Jernigan on LinkedIn: https://www.linkedin.com/in/andrewjernigan/

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.