Full Episodes | Insurtech Leadership Podcast

The Insurtech Leadership Podcast
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Full-length episodes and replays from The Insurtech Leadership Podcast. New here? Start with the newest episode and work backwards.

  1. 1d ago

    The 30-Year-Old Software Running Your Underwriting Is Already Obsolete

    Introduction Most carriers are still running underwriting on policy admin systems built three decades ago — stitched together through a hundred acquisitions and never designed to work with AI. Federato is betting the only way to fix that is to replace it entirely. William Steenbergen is the co-founder and CTO of Federato, the first AI-native platform built to cover the full commercial insurance policy lifecycle. He started in reinforcement learning research before spending five months in a cabin in Idaho interviewing underwriters until he understood the problem well enough to build a solution. Federato has since raised $100 million from Goldman Sachs and is now live across commercial lines from SMB to large enterprise. In this conversation, Josh Hollander and Steenbergen dig into why bolting AI onto legacy systems keeps failing, what the underwriting workflow looks like inside an AI-native platform, and why Federato has started turning away customers who aren't ready to make the full switch. Guest Bio William Steenbergen is the Co-Founder and CTO of Federato, an AI-native platform covering the full commercial policy lifecycle — from email submission through rating, quoting, binding, issuance, endorsements, and renewal. He conducted reinforcement learning research at Stanford before co-founding Federato in 2020, spending over a thousand hours interviewing underwriters before writing a line of code. Federato raised $100 million from Goldman Sachs in 2024. Key Topics Why legacy systems can't run AI agents — Old core policy admin systems have been stitched together through 100+ acquisitions. The data and tools don't live in a standardized way, making it nearly impossible for AI agents to access the context they need to act — not just summarize. The three things an AI agent needs — An LLM, context (submission data, product definitions, claims history, forms), and tools it can interact with to take real action. Most incumbents can't provide all three in an AI-native way. What underwriting looks like now — Ten minutes after an email submission arrives, the underwriter logs in to find it already quoted. They review the AI agent's reasoning, citations, and assumptions, then approve, adjust, or ask follow-up questions in plain text — structurally identical to reviewing a referral. 95% accuracy vs. a room full of humans — Federato ran a study comparing AI agent outputs to human underwriter decisions on the same policies. The agent matched humans 95% of the time and showed less variance than ten humans working the same policy independently. Turning away the wrong customers — Federato now declines prospects who want to use the platform as a workbench on top of a legacy policy admin system. The only configuration that works is replacing the policy admin system entirely. AI regulation and accountability — Underwriters still review and approve every AI-generated quote. The AI runs deterministic tools — the rater, the filed forms — it can only make mistakes on the inputs it sends, not the outputs those tools generate. Notable Quotes "We're not trying to tack on AI onto an existing process. We're re-envisioning what a good insurance and underwriting process actually looks like." "When an AI agent interacts with the rater, it doesn't make up the premium. It still runs a deterministic rater. The tool is deterministic." "If you're not subscribed to doing a full policy lifecycle in Federato and actually replacing your policy admin system, you're probably not the right customer for us." Resources Guest: Federato: https://www.federato.ai William Steenbergen on LinkedIn: (verify and add URL) Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast: 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, Apple Podcasts, and Spotify.

    31 min

  2. 4d ago

    AI Is Breaking the Old Rules of Monetization

    Introduction The rules that governed software pricing for a decade are breaking down. Per-user SaaS models made sense when users were people. Now that AI is automating those seats, the pricing logic collapses — and carriers, brokers, and insurtech vendors are all rethinking the economics at the same time. Michael Nadel is a partner and head of the global insurance practice at Simon-Kucher & Partners. He joined Josh Hollander for his second appearance on the show to dig into what the AI era is actually doing to monetization — from the pricing mistakes early movers keep making, to why outcome-based models are harder to execute than they are to sell, to a 50,000-session LLM shopping simulation that revealed what could become the next SEO arms race for insurance carriers.   Guest Bio Michael Nadel is a partner and head of the global insurance practice at Simon-Kucher & Partners, a global strategy consultancy focused on growth, pricing, and monetization. Before consulting, he spent time at CNA in strategy and innovation, and earlier led large-scale financial services implementation work at Accenture. He advises carriers, brokers, MGAs, and insurtech vendors on pricing strategy, and co-hosts an annual monetization masterclass at InsureTech Connect.   Key Topics From offense to defense — A year ago, clients asked how to monetize new AI features. Today the questions are more defensive: how does AI threaten my core product, my pricing model, and my existing revenue base? The two biggest AI pricing mistakes — Pricing before understanding what customers actually value, and jumping to outcome-based models before you can define or reliably deliver the outcome. Outcome-based pricing is the destination, not the shortcut — Buyers love paying only when value is delivered. The problem is definitional complexity — what counts as the outcome, who controls it, and what happens when results fall short. AI spend that looks like RPA in new packaging — Carriers running well-designed AI programs focus on workflow economics, not technology for its own sake. The recommended split: 70% on high-value workflow automation, 20% on data and governance, 10% on exploratory bets. GEO: the next SEO — Simon-Kucher simulated 50,000 insurance shopping sessions across 50 consumer personas and three major LLMs. What gets a carrier recommended by an LLM is not the same as what gets them ranked on Google. CMOs need to decide how to treat LLMs as a distribution channel now. Services businesses face the same disruption — Pure labor arbitrage is structurally challenged by AI. Firms that survive will combine domain expertise with AI-enabled delivery and evolve from vendors to partners.   Notable Quotes "You need to understand what people value before you prescribe a price. But very often, people build something, bring it to market, and then try to figure out why it isn't selling." "Automating a bad process simply creates a faster bad process." "It's not replacing system X with system Y — it's changing the way you work fundamentally. Orange juice to lemonade. Not a better way to make orange juice." "Last year, roughly one percent of our traffic came from LLMs. This year it was roughly five percent and increasing."   Resources Guest: Simon-Kucher & Partners: https://www.simon-kucher.com Michael Nadel on LinkedIn: (verify and add URL) Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast: 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, Apple Podcasts, and Spotify.

    47 min

  3. Jun 19

    Behavioral Intent in the Age of Agentic AI: The ForMotiv Growth Story

    Introduction Carriers have spent decades building underwriting models on structured data - loss history, credit scores, telematics - while ignoring one of the richest signals available: how people actually behave when they fill out an application. ForMotiv was built on the premise that digital body language is predictive, and after nearly a decade of proving it, the company just hit profitability. Woody Klemmer is the co-founder and Head of Growth at ForMotiv, a behavioral analytics platform now embedded across the majority of the top ten U.S. carriers. In this conversation, Josh Hollander and Klemmer dig into the growth paradox carriers can't escape, what agentic AI fraud actually looks like at the application layer, and why the build-versus-buy math on behavioral data almost always favors buying. Guest Bio Woody Klemmer is the Co-Founder and Head of Growth at ForMotiv, a behavioral analytics platform purpose-built for the insurance industry. ForMotiv captures digital body language - hesitations, edit patterns, corrections, and interaction behaviors - from online applications and turns them into real-time signals for conversion, risk, and fraud decisions. Klemmer has spent nearly a decade growing the business from a direct-to-consumer tool to an enterprise-wide behavioral intelligence layer serving the majority of the top ten U.S. carriers. Key Topics The growth paradox — Every tactic carriers use to grow inadvertently lowers the barrier for misrepresentation and fraud. The impact catches up 12 to 24 months later in loss ratios. ForMotiv's thesis is that behavioral intelligence can break this either/or dynamic between growth and risk. Intent is two-dimensional - Conversion likelihood on one axis, risk profile on the other. A high-intent applicant who backed into their garage is a fundamentally different underwriting risk than one who just bought a new car. The Year of the Agent - ForMotiv sold more agent-related solutions than direct solutions for the first time in 2024. Agents know underwriting thresholds and how to game the system. Agent scorecarding and benchmarking tools are now being used for fraud detection, SIU referrals, and new hire training. Enterprise intent - In 2026, ForMotiv embeds across the full policy lifecycle from first quote to claims, providing a unified behavioral thread across systems that have traditionally been siloed. Agentic AI detection is live - ForMotiv can identify when an AI agent is completing an application. Carriers are still deciding what to do with that signal, but the detection capability exists today. First-party data as a model input - Carriers incorporating ForMotiv's behavioral dataset into existing predictive models are seeing measurable jumps in predictive lift from a genuinely novel data source. Notable Quotes "Carriers are faced with what we call a growth paradox - the mechanisms they use to grow inadvertently increase risk. And that usually catches up 12, 18, 24 months later." "We had a carrier say the quiet part out loud: our worry is we're getting the bad business that you're helping protect the other carriers from." "When people ask who our biggest competitors are, I always say bandwidth and budget. We're sunscreen - protective, but not a necessity until we're integrated." "The JavaScript component isn't the value. What we've done over a decade is feed it all back to you in 40 milliseconds." Resources Guest: ForMotiv: https://www.formotiv.com Woody Klemmer: https://www.linkedin.com/in/woodyklemmer/ Host & Organization: Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast: 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, Apple Podcasts, and Spotify.

    36 min

  4. Jun 12

    The Distribution Infrastructure Gap: What Carriers Keep Getting Wrong

    Introduction Most distribution management tools were built in the nineties and haven't changed much since. Carriers and MGAs are onboarding agents manually, tracking licenses in spreadsheets, and managing compliance through email threads. Ido Deutsch spent nine years solving that problem from the inside - before realizing the solution was worth selling to the rest of the market. Deutsch is the co-founder of ProducerFlow, a distribution management platform that started as an internal tool at Agentero, the digital insurance network he helped build from a single client and barely a product in 2016 to a scaled distribution business. When carriers kept asking how Agentero was handling agent onboarding so efficiently, Deutsch knew the tool had a market of its own. ProducerFlow launched as a standalone product in March 2024. In this conversation, Josh Hollander and Deutsch dig into what carriers and MGAs consistently get wrong about distribution infrastructure, why the market no longer accepts SaaS-only tools, and why fixing your data before layering in AI is the only move that matters. Guest Bio Ido Deutsch is the Co-Founder of ProducerFlow and Head of Go-to-Market at Agentero, a digital insurance network connecting carriers, MGAs, and independent agencies. A serial entrepreneur who grew up in Israel and built three companies before moving to the US in 2014, he joined Agentero's founder Luis Pino while still at Berkeley's MBA program and spent the next nine years building the company's distribution network and technology from scratch. ProducerFlow, launched in 2024, automates agent onboarding, licensing, compliance, and distribution management for carriers and MGAs. Key Topics • Built from necessity, not theory - ProducerFlow wasn't designed in a whiteboard session. It was built because Agentero was onboarding hundreds of agencies a month and couldn't keep up manually. The existing market solutions were either too old, too rigid, or too expensive. So they built their own, and carriers started asking to use it. • The best clients are switching from something - Deutsch's most successful clients aren't building from scratch. They've already tried one of the legacy tools, overpaid, been underdelivered, and are ready for something that actually integrates with their existing stack. That frustration is the clearest buying signal. • SaaS-only is no longer enough - The market has shifted. Carriers don't want a tool; they want an outcome. ProducerFlow offers a full managed service for clients who want to outsource compliance entirely, or infrastructure-only for those who want to run it themselves. The key insight: whoever wins in distribution tech has to be willing to do the work, not just sell the platform. • Fix the data before you touch the AI - Deutsch's consistent message across the conversation: AI is only as good as the data it runs on. He's seen top-five carriers and major brokers with years of data that's disorganized, siloed, and hard to query. Layering AI on top of bad infrastructure gives confident wrong answers. Fix the foundation first. • Speed to onboard is the core metric - The time from meeting a new agency to the moment they can quote and bind is ProducerFlow's north star. Faster onboarding means better agent experience, higher retention, and more written premium. Everything else is secondary. • The CIO is gaining ground - Deutsch has watched the power dynamics inside carrier organizations shift. Head of AI titles are proliferating, but the real influence is moving toward CIOs and information security leaders as data privacy, AI governance, and "where does my data go" questions dominate every sales cycle. Notable Quotes "We couldn't find anything that worked for us. So we built our own. And then carriers started asking, how do you do that?" "Our best clients typically tried the solution already. They overpaid, were underdelivered, and then they see how ours works. We try not to over promise, but we definitely over deliver." "The market doesn't really accept SaaS-only tools anymore. They want you to solve an outcome, replace a whole function, and do the work." "Fix your data and fix how you look at things. Everything is going to be based on that. AI is only as good as your infrastructure. If the data isn't right, it will just give you very confident answers that are wrong." Resources Guest: • ProducerFlow: https://www.producerflow.com • Ido Deutsch on LinkedIn: https://www.linkedin.com/in/ido-deutsch/ 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, Apple Podcasts, and Spotify.

    30 min

  5. Jun 8

    What 50 Carriers Know That You Don’t: Inside Sønr

    Introduction Most insurers say they want to be innovative. Fewer have a systematic way to know what's worth pursuing, who's building it, and whether they should partner, invest, or simply wait. Matt Connolly has spent ten years building the answer to that problem. Connolly is the founder of Sønr, a global market intelligence platform that tracks over five million companies and helps insurers, reinsurers, and brokers make better decisions about innovation and technology. Working with fifty-plus tier-one carriers—from Travelers and Liberty Mutual to Munich Re, Allianz, and Tokio Marine—as well as brokers like Guy Carpenter and WTW, Sønr sits at the intersection of the startups changing the industry and the incumbents that need to understand them. In this conversation, Josh Hollander and Connolly dig into where innovation intent breaks down inside large carriers, the four points where value leaks out of a corporate innovation process, why POC purgatory is a symptom not the disease, and how Sønr 2.0 is bringing market intelligence to operators who've been tasked to innovate but not given the tools to do it. Guest Bio Matt Connolly is the Founder and CEO of Sønr, a global insurtech market intelligence platform used by fifty-plus tier-one insurers, reinsurers, and brokers worldwide. Founded ten years ago, Sønr tracks over five million companies and has built a proprietary data set on insurance innovation unavailable to general AI platforms. He also hosts his own podcast interviewing innovation leaders from major global carriers. Sønr now generates half its revenue from North America and recently made its first US hire. Key Topics • Where innovation intent breaks down — At the CEO level. Without clear sponsorship and direction from leadership, innovation functions become disconnected from real business priorities. Ten years of data backs this up. • The four value leaks — Not understanding trends, poor scouting discipline, year-long POCs that should be three weeks, and failing to move from POC to pilot to scale. Each is a distinct failure mode with a distinct fix. • POC purgatory — Mature innovation programs are running more POCs than ever but scaling fewer. The root cause is almost always people: wrong sponsors, wrong internal champions, or wrong startup for the actual need. Sønr's fix: a one-day workshop to build a mini business case before a three-week POC begins, with KPIs and go/no-go criteria agreed upfront. • The decentralization of innovation — Carriers that once had centralized innovation functions have spread that mandate across underwriting, claims, and distribution—but capability hasn't followed. Operators have been tasked to innovate with no networks, no tooling, and no experience. This is the gap Sønr 2.0 addresses. • Sønr 2.0 and the Emerging Trends Academy — A simple front-end into ten years of proprietary insurance innovation data, priced for operators not just innovation teams. The Emerging Trends Academy goes deeper: cross-industry groups going deep on specific trends with startups, carriers, consultants, and academics in the same room. • The data moat — Ten years of tracking every company, trend signal, and client engagement within insurance innovation. Data that Connolly notes even Anthropic or OpenAI simply can't access. That compounded intelligence sits behind both the platform and the research offering. Notable Quotes "Don't go with the startup that is the best salesperson. Do the scouting properly—where are they based, what's their culture, who are their people, does the technology align to your needs?" "POC purgatory. We're seeing mature innovation businesses doing more POCs than ever but not moving beyond them. The answer is often the people." "The data we sit on is not available to anybody else. It's compounded intelligence from ten years. Anthropic or OpenAI simply can't get to it." "If you don't get your direction right from the top, the value leak is going to be huge later on. Just start in the right place." Resources Guest: • Sønr: https://www.sonr.io • Matt Connolly on LinkedIn: https://www.linkedin.com/in/wearematt/ 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, Apple Podcasts, and Spotify.

    29 min

  6. Jun 1

    The $2M Mistake: How Global Insurtechs Burn Cash Entering the U.S.

    Introduction International tech companies burn through $2 million trying to crack the US market every day. Not because their product is wrong. Because they hire a sales team before they have a sales motion. Dan Griffith has spent 15 years watching this mistake play out—and building the playbook to prevent it. Griffith is the founder of Greater Gain Group, a go-to-market firm that helps software and technology companies—most of them international—land and scale in US insurance, financial services, and healthcare markets. As the first US hire for a South African company, he scaled it from $3M to $150M in three years. Those hard lessons became the foundation for Greater Gain Group's 90-day go-to-market framework. In this conversation, Josh Hollander and Griffith dig into why the unicorn sales hire is the most dangerous move an international founder can make, what has to be true before you put a rep in a seat, and where the insurtech market is creating real demand for cross-border go-to-market right now. Guest Bio Dan Griffith is the Founder and Principal Consultant at Greater Gain Group, a go-to-market consultancy specializing in helping international software and technology companies enter and scale in the US insurance, financial services, and healthcare markets. With 30 years in enterprise sales and marketing, he has served as a first US hire and go-to-market architect for companies entering from South Africa, France, Europe, and beyond. His 90-day framework takes founders from "we're entering the US" to a repeatable sales motion—without the $2M mistake. Key Topics • The $2M mistake — A VP of Sales, two account executives, a marketing hire, an office, and conference travel. You're at $2M in under a year with nothing built and no pipeline. Fifty percent of Greater Gain Group's clients have already made this mistake before they call. • Don't hire salespeople (yet) — The tell that a founder is about to flame out: they say they're going to hire a sales team. Griffith's rule: build the sales motion before you build the team. A rep can't fly a plane that hasn't been designed. • The founder has to come — For companies under $50M, having a founder on the ground for early US conversations is the strategy. Hearing objections directly is how you convert from founder-led to team-led sales—the transition Greater Gain Group is built to facilitate. • Three to five segments, not one — Pick no fewer than three and no more than five market segments, understand the pain in each, and build an outreach engine that generates sales conversations—not leads. Leads have no value. • Paid pilots and MSA reality — US buyers do paid pilots. Free pilots signal low value and waste time. On contracts: insurance companies have ten times more lawyers than you. Know your non-negotiables, keep the list short, and don't let MSA rigidity keep you out of the market. • Price higher than you think — International companies consistently underprice the US market by 20–40%. Corporate budgets at US insurers are significantly larger than abroad. One client was surprised a health insurer's CTO had $475K of year-end budget left for a POC they'd hesitated to price. Notable Quotes "They hand you your laptop and say, go sell us some stuff. I learned a lot of hard lessons on how not to do things." "If you don't bring value, you're out. The US market is transactional. As much as I hate to say it." "A lead has no value. Build an outreach engine that generates sales conversations." "Your only competitor is the status quo. If you're getting into a feature-function-benefit argument, you've already lost." Resources Guest: • 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, Apple Podcasts, and Spotify.

    29 min

  7. Jun 1

    The $13B Last Mile: Why Leak Detection Never Gets Installed

    Introduction   Non-weather water damage costs insurers $13 billion a year. Interior leaks account for 39% of all homeowner claims. And yet most carriers still treat prevention as a brochure recommendation—send the homeowner a discount offer, hope they find a plumber, and call it a program. Paul Vacquier thinks that's why it isn't working.   Vacquier is the founder and CEO of Beagle Services, a water security company that solves the last-mile problem carriers and homeowners can't solve on their own: getting leak detection hardware actually installed, monitored, and maintained. A California-barred litigation attorney turned insurtech operator, he built the insurance carrier playbook at Flow Technologies before Moen acquired it. What he learned there—that the technology exists but deployment at scale does not—became the genesis for Beagle.   In this conversation, Josh Hollander and Vacquier dig into why the installation gap is where loss prevention falls apart, how the industry is shifting from carrot to stick on water shutoff requirements, and what Beagle's work with carriers like PURE tells us about where prevention programs are actually headed.   Guest Bio   Paul Vacquier is the Founder and CEO of Beagle Services, a water security company operating across 17 states that installs, monitors, and maintains automatic water shutoff valves and leak detection systems for insurance carriers, brokers, and homeowners. Before founding Beagle, he built the insurance carrier go-to-market at Flow Technologies, which was later acquired by Moen (now Flow by Moen). He is a California-barred litigation attorney who came to insurtech through the startup world.   Key Topics   • The last-mile problem nobody solved — Leak detection technology has existed for over a decade. The gap isn't the hardware—it's professional installation, ongoing monitoring, and maintenance at scale. Carriers recommend devices; homeowners can't find qualified installers; the device sits in a box. Beagle exists to close that gap.   • From carrot to stick — Carriers are shifting from discount incentives ("send us a photo of your installed valve") to hard underwriting requirements at specific coverage thresholds. High-net-worth carriers like PURE have led the way. Standard lines carriers are following. The stick is now backed by data.   • The compliance illusion — A photo of an installed device and a paid invoice doesn't mean the system is on and actively protecting the home. The same problem exists with alarm systems: discounts are given, but nobody checks if the alarm was set before you left for vacation. Beagle's Watchdog product monitors device status—online, offline, alert conditions—in real time.   • What Beagle does with the data — Watchdog ingests alert data across every installed system: high pressure, small drips, thermal expansion risk, shutoff frequency, device connectivity. When an alert fires, Beagle dispatches a service visit to fix the underlying problem—toilet flappers, angle stops, pressure regulators—before it becomes a claim.   • Scaling a physical services business — Unlike SaaS, physical services don't go straight to margin as you grow. The key variable is drive time: how many installs can a technician complete per day in Atlanta, Los Angeles, or Dallas? Beagle grows market-by-market only when carrier partners generate enough demand to support a full-time local team, which drives economies of scale that lower costs for everyone.   • AI can't turn a wrench — Beagle uses AI for route optimization and operational efficiency, and is training internal models as a knowledge base for field technicians and customer service. But the core product requires humans on-site at every property. No bot can cut the pipe.   Notable Quotes   "Most carriers still treat prevention as a brochure recommendation rather than an operational program."   "You'd have a picture of the installed device and a paid invoice—but that doesn't necessarily mean the system is on and active protecting the home."   "The AI can't turn a wrench. No matter how smart the valves get, you still have to put it on. Until that day comes, we'll be here."   "Beagle's intent is to be a proactive, preventative maintenance plumbing company. All we do is referred-in work to help prevent leaks from occurring."   Resources   Guest: • Beagle Services: https://www.beagleservices.com • Paul Vacquier on LinkedIn: hhttps://www.linkedin.com/in/paulvacquier/   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, Apple Podcasts, and Spotify.

    28 min

  8. May 21

    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 Subscribe & Review 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.

    30 min
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Full-length episodes and replays from The Insurtech Leadership Podcast. New here? Start with the newest episode and work backwards.

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