Full Episodes | Insurtech Leadership Podcast

Introduction What happens to a $114 billion market when six people head toward retirement for every one person coming in behind them? That is the question hanging over the MGA channel, and it sits at the center of Vertafore's 2026 MGA Workforce and Technology Report. Josh Hollander sits down with Emily McGinn, who runs Vertafore's MGA & Wholesale business unit, to dig into what a survey of nea...

Introduction What makes an underwriter act on an AI's answer? Not the accuracy of the model, according to Stan Smith, but whether the person can see how the model got there. Josh Hollander sits down with the founder and CEO of Gradient AI, whose platform is trained on a contributory data lake of tens of millions of policies and claims, to talk about explainability as the last mile of AI adoption,...

Introduction Most insurance executives have heard the AI pitch a hundred times by now, and most of those pitches collapse the moment they hit a real call center, a real compliance team, or a real broker's quoting workflow. The interesting question is no longer whether AI works in insurance. The question is what deployment method survives a regulated, audited, multi-channel customer operation, and...

Introduction What happens to your health coverage the day you leave a job, go independent, or pick up seasonal work? For more than 90 million Americans who earn outside a traditional employer plan, the answer is usually that it disappears. Felix Ortiz, founder and CEO of Smirk Health, joined host Joshua Hollander to explain why the benefits system built in 1929 for full-time employees no longer fi...

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 po...

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 & Pa...

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....

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-...

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, rein...

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 an...

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 wat...

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...

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...

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 theore...

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 Co...

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 ye...

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 lo...

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 technol...

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 serv...

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 retentio...

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,...

Introduction What happens when you stop trying to make claims adjusters faster and instead redesign the entire workflow from first notice of loss? Most insurers are layering AI co-pilots on top of legacy processes, but Ravin AI is arguing for something more disruptive: a fully automated claims pipeline that collects evidence, detects fraud, applies business rules, and routes decisions before a hum...

Episode Overview How many insurance organizations have launched an AI pilot, watched it work in the lab, and then watched it quietly disappear in production? Today we're dismantling the myth that AI adoption is a technology problem—and making the case that it's a workflow problem. Guest Jake Sloan, VP of Global Insurance at Appian, is an operator first. He has run large-scale insurance operations,...

Episode Overview What does it actually take to run a digital insurance operation at the system level—not at the chatbot layer, but at the transaction layer? Joshua R. Hollander speaks with Wayne Slavin, CEO and Co-Founder of Sure, about the infrastructure required to deliver true digital insurance in an AI-agent world. Wayne describes Sure's role as "what Visa and Mastercard were in the early days...

What if your insurance product didn't need a claims adjuster? When you remove the blame from the coverage equation, everything changes. In this episode, Randel Bennett walks through how no-fault embedded insurance—specifically parametric insurance woven into the solar energy business—is reshaping how performance guarantees work in commercial infrastructure projects. About the Guest Randel Bennett...