FNO: InsureTech

In Episode 305 of the FNO: InsureTech Podcast, hosts Rob Beller and Lee Boyd welcome Andrew Yeoman, Co-founder and CEO of Concirrus, joining from the UK. Andrew shares how his company is transforming specialty insurance underwriting through AI powered automation, domain specific intelligence, and a relentless focus on real business outcomes.

Andrew explains how Concirrus helps insurers dramatically reduce manual work, accelerate quoting, and unlock underwriting capacity without increasing headcount. Drawing on years of experience across insurance and technology, he offers a unique perspective on why AI alone is not the differentiator and why the real opportunity lies in rethinking business models around it.

The conversation goes beyond today's use cases, exploring the concept of "but for" companies which are businesses that only exist because of AI and what that means for the future of insurance, underwriting, and entrepreneurship.

[03:45] Andrew Yeoman Joins from the UK A multinational episode kicks off with Andrew introducing his background and proximity to the heart of the insurance market near Lloyd's of London.

[05:00] Award Winning AI in Action How Concirrus helped a customer grow from 25M to 100M in premium without increasing headcount, earning top industry AI awards.

[07:30] What Concirrus Actually Does An overview of the platform automating the entire underwriting lifecycle from submission ingestion to quote, bind, and policy administration.

[09:30] Automating the Work Underwriters Don't Want to Do Why eliminating administrative tasks roughly 40 percent of an underwriter's time unlocks productivity and improves job satisfaction.

[11:15] From 48 Hours to 90 Seconds How AI driven workflows reduced time to quote by over 90 percent, transforming responsiveness and competitiveness.

[12:45] Why One Size AI Doesn't Work in Underwriting The importance of domain specific AI models tailored to different specialty lines like aviation, marine, and crisis risk.

[16:30] The Evolution Toward Specialty Insurance How early lessons in data overload and usability led to a focus on simplifying underwriting in complex, underserved specialty markets.

[20:30] Reinventing the Company Around AI Andrew shares how Concirrus reset in 2023, leveraging AI at the right moment to rebuild with strong domain expertise.

[22:00] Why "AI Native" Is Becoming Meaningless A candid take on how AI is quickly becoming table stakes not a true differentiator.

[23:30] The Rise of "But For" Companies A powerful framework businesses that only exist because of AI and why they represent the next wave of innovation.

[27:15] The Idea of the One Person Insurance Company Exploring the possibility of a billion dollar MGA run by a single person supported by AI agents.

[29:30] New Insurance Products Enabled by AI How dynamic, adaptive policies could optimize coverage in real time based on customer behavior and context.

[33:10] A Golden Age for Insurance Innovation Why Andrew believes we are entering an unprecedented era of opportunity driven by AI and technological advancement.

[34:45] Can the Industry Keep Up? Why MGAs may lead innovation while carriers provide the balance sheet and how the ecosystem evolves together.

[36:00] The Role of Vendors in an AI World Why success comes from clearing the path for customers not pushing technology for its own sake.

[39:30] Global Risk, War, and Real Time Data How geopolitical events create cascading impacts across specialty insurance lines and why real time insight is critical.

[43:00] Final Thoughts The Future Is Already Changing A reflection on AI agents, automation, and how entrepreneurship itself is being redefined.

In Episode 304 of the FNO: InsureTech Podcast, hosts Rob Beller and Lee Boyd welcome back Kyle Nakatsuji for his third appearance on the show. Kyle is the CEO and Founder of Clearcover and the founder of Dearborn Labs, a new venture focused on helping insurance organizations turn AI from strategy into execution.

Kyle explains how Dearborn Labs helps carriers, MGAs, and agencies cut through AI noise, identify high impact use cases, and implement solutions that deliver real business results. Drawing on nearly a decade of deploying production AI, he shares practical insights from claims and operations, why execution and adoption matter most, and why waiting to act is becoming increasingly risky.

Kyle also shares a brief update on Clearcover as it enters its tenth year, including improved underwriting results, a return to growth, and the launch of Clearcover Access in Florida.

[03:05] Kyle Nakatsuji Returns for His Third Appearance Why this moment feels different for AI adoption across the insurance industry.

[05:10] Clearcover at Ten Years How a renewed focus on underwriting discipline and loss ratios set the stage for growth.

[07:40] Launching Clearcover Access in Florida Why flexible payments and predictable fees better reflect how policyholders manage money.

[10:25] The Origin of Dearborn Labs What Kyle saw in the market that led him to launch a firm focused on AI execution, not theory.

[13:10] Why Insurers Are Drowning in AI Noise How vendors, pilots, and strategy decks distract from real business impact.

[16:00] Discovery Before Deployment Why identifying the right problem to solve is the most important step in any AI initiative.

[18:55] AI Agents in Claims Operations How Clearcover uses AI to replace recorded statements and reduce claim cycle times by up to three days.

[22:30] Adoption Matters More Than Technology Lessons learned from rolling out AI tools inside a regulated insurance environment.

[26:00] Cross Functional Agent Based Workflows Why claims, underwriting, and operations must work together for AI to deliver value.

[30:15] Humans, Oversight, and Judgment in an AI Driven World What roles remain uniquely human as AI takes on more knowledge work.

[34:10] The Cost of Waiting Why delaying meaningful AI adoption is becoming riskier for insurers.

[37:45] What Comes Next for AI in Insurance Kyle's perspective on where agent based systems are heading and how insurers can prepare now.

In Episode 303 of the FNO: InsureTech Podcast, host Lee Boyd welcomes Phil McGriskin, Co-Founder and CEO of Vitesse, for a deep and timely discussion on one of the most complex, and often invisible, challenges in insurance: financial infrastructure behind claims payments.

Phil shares his journey from Australia to the heart of the Lloyd's insurance market, tracing a career that spans underwriting, brokerage, fintech entrepreneurship, and large scale payments innovation. With multiple successful ventures behind him, Phil brings a rare perspective to insurance, approaching long standing problems through the lens of payments, treasury, and operational control.

The conversation explores how Vitesse was built to solve the inefficiencies surrounding loss funds, delegated authority payments, and treasury visibility. Rather than focusing solely on speeding up payments, Phil explains why giving carriers real time insight, control, and transparency over capital is foundational to improving claims outcomes, reducing risk, and freeing trapped funds.

Lee and Phil also discuss what it took to deliver meaningful change inside the 300 year old Lloyd's ecosystem, how fintech principles must adapt to insurance regulation, and why modernizing financial infrastructure requires collaboration across carriers, TPAs, MGAs, and brokers.

The episode closes with Phil's pragmatic perspective on artificial intelligence within financial infrastructure, where AI can create real value today, and where human judgment and accountability must remain firmly in place.

[05:30] – Phil McGriskin's Early Career, Moving from Australia to the Lloyd's Market How Phil's early experience in underwriting and brokerage shaped his understanding of insurance complexity.

[09:15] – The Origins of Vitesse and Lessons from Building Global Payments Companies Why Phil returned to payments after exiting his first fintech business and what insurance was missing.

[13:40] – Why Loss Funds and Treasury Visibility Became the Core Problem to Solve How carriers unknowingly tied up millions in poorly reconciled delegated authority funds.

[18:55] – Modernizing Claims Payments Inside the Lloyd's Ecosystem What it took to deliver the Faster Claims Payment initiative across a 300 year old marketplace.

[21:45] – Scaling Fintech in a Highly Regulated Insurance Environment Balancing innovation, regulation, and the realities of legacy insurance operations.

[25:10] – Implementing Technology Across Carriers, TPAs, and MGAs Why successful transformation requires engaging every party in the insurance value chain.

[29:20] – Expanding into the U.S. Through Lloyd's Connectivity and Regulatory Licensing How Vitesse leveraged existing market relationships to establish a U.S. footprint.

[32:40] – Carriers, TPAs, and the Role of Tier One Banking Infrastructure Why treasury safety, regulation, and bank selection matter in insurance payments.

[36:30] – Phil McGriskin on Responsible AI in Financial Infrastructure Where AI adds value today in treasury optimization and operations, and why humans must retain control over payment authorization.

[40:15] – The Future of Financial Infrastructure in Insurance Why shared platforms, transparency, and trust will define the next phase of insurance innovation.

In this episode of the FNO: InsureTech Podcast, Rob Beller sits down with a fascinating guest, Eran Tirer, to explore his entrepreneurial journey and the path that led him to found Ledgertech, a company focused on building technology that helps insurers launch and scale embedded insurance solutions within the global insurance ecosystem.

Eran shares lessons from decades of building enterprise software companies, including the story behind EasySource and its eventual acquisition by IBM. The conversation explores the realities of building technology for large enterprises, navigating legacy infrastructure, and identifying opportunities for innovation within complex industries.

A major focus of the discussion is the role of embedded insurance as both a distribution model and a catalyst for digital transformation. Eran explains how Ledgertech initially used embedded insurance as a strategic entry point into the market, helping insurers launch new digital products quickly while integrating with existing systems. From there, the company expanded its capabilities to support insurers looking to modernize their technology stack and participate in the evolving digital ecosystem.

[09:00] – How Early Military Leadership Shaped Eran Tirer's Entrepreneurial Journey

[16:00] – Founding EasySource and Solving the Legacy Systems Challenge

[19:00] – When Competing with IBM Turned into an Acquisition

[27:00] – Why Ledgertech Entered the Insurance Technology Market

[40:00] – How Ledgertech Uses Embedded Insurance to Accelerate Digital Transformation

We kickstart our 300+ episodes era with Bobby Touran, Co-Founder and CEO of Rainbow, as Rob Beller and Lee Boyd sit down with him to unpack how he built Rainbow, a technology-enabled MGA laser-focused on modernizing coverage for restaurants and other specialty commercial risks. Bobby walks through Rainbow's "inch-wide, mile-deep" philosophy, explaining why going all-in on a single vertical and owning the underwriting systems, technology, and distribution that support it creates a durable competitive advantage that generalist carriers simply can't replicate.

Key Highlights

• (07:35) How an accidental path through a fintech incubator led Bobby to co-found Path Point and eventually Rainbow

• (10:42) What Rainbow builds and why the agent channel is central to their loss ratio strategy

• (17:04) How Rainbow combines experienced underwriters with technology for a balanced approach to risk evaluation

• (19:44) Continuous underwriting explained and how Rainbow re-evaluates policies every single day

• (24:28) The core coverages most restaurants need and why some are harder to place than others

• (27:22) The real risk drivers in restaurant insurance including liquor liability and fire

• (30:11) How data pipelines continuously monitor operational changes to keep underwriting current

• (40:11) Expanding beyond restaurants into beauty and wellness using the same platform

Episode 300 is a milestone we never imagined when we hit record for the first time in 2018 at 470 Claims, which was acquired by Alacrity Solutions. Seven years later, Rob and Lee sit down to reflect on how FNO: InsureTech began, how it evolved, and what has surprised us most along the way.

In this special episode, we talk through the genesis of the podcast and how a simple idea turned into hundreds of conversations across insurance and insuretech. We reflect on the consistency, curiosity, and commitment it took to keep showing up week after week, and how the journey shaped us as hosts.

Key Highlights

• [3:19] The genesis of FNO: InsureTech and how the podcast started in 2018 • [9:03] The unexpected relationships and networking that grew from the show • [25:42] How insuretech conversations evolved from APIs to AI • [29:36] The industry shifts between 2018 and 2025 that quietly changed startup thinking • [31:09] Reflections on seven years of recording and the plans ahead We are grateful to everyone who has listened, shared, or joined us as a guest, and to our sponsor Alacrity Solutions for supporting us all these years. Cheers to the next 100!

In this episode of FNO: InsureTech, Rob Beller and Lee Boyd welcome Heather Wilson, CEO of CLARA Analytics, for an insightful conversation on how AI is transforming claims intelligence and reshaping the competitive landscape of insurance. Heather shares how CLARA Analytics has been doing 'AI before AI was cool' since 2012, building a platform that now processes millions of claims with 24/7 predictive analytics, and reflects on her own journey as a data science pioneer who has always been years ahead of industry trends.

The discussion explores CLARA's hybrid model that blends AI-driven insights with traditional adjuster expertise, the challenges of building trust in automated systems, and why the future competitive advantage in insurance won't be pricing. Heather offers candid perspectives on the "AI psychology" holding the industry back, the generational expectations that will force change, and why empathy and human judgment remain irreplaceable even as agents handle 80% of the work.

• [01:49] The founding thesis behind CLARA Analytics and what happens when AI models work while adjusters sleep.
• [05:16] Why CLARA was building AI solutions in 2012 when most people didn't even know what the technology meant.
• [06:51] A surprising analogy that explains why even the most experienced professionals still need AI in their workflow.
• [12:43] How CLARA measures and attributes financial impact to every action an adjuster takes based on AI recommendations.
• [18:25] Why building AI is faster than ever, but there's still one massive obstacle slowing everyone down.
• [21:44] Why the next competitive advantage in insurance isn't pricing, and what will actually determine who wins.
• [27:11] Heather's prediction for when agentic AI will fundamentally reshape the competitive landscape in insurance.
• [38:38] The mental barrier Heather calls "AI psychology" and why it's holding the insurance industry back from transformative change.
• [39:40] What Gen Alpha and Gen Z will say when they look at insurance, and why the industry is running out of time to respond.

In this episode of FNO: InsureTech, Rob Beller and Lee Boyd welcome Stacey Brown, Founder and President of InsurTech America, for a thoughtful conversation on how curiosity, timing, and community can quietly reshape an industry. Stacey shares reflections from his career in insurance technology, the early signals that convinced him something new was forming in insuretech, and the personal decision that led him to step beyond a traditional corporate path.

The discussion follows the evolution of InsurTech America from small, informal gatherings into a growing network of regional communities, touching on the challenges of scale, the importance of trust, and the realities of building something without a predefined blueprint. Along the way, Stacey offers perspective on how industry events create unexpected collisions, why adaptability matters more than polish, and what it takes to keep people genuinely engaged as the insuretech landscape continues to mature.

Key Highlights

• The seemingly ordinary moment that became the catalyst for Stacey Brown to start building an insuretech community.

• How early exposure to new ideas and unfamiliar industry models reshaped Stacey's understanding of insurance as a whole.

• The role of small, unstructured meetups in creating momentum before insuretech became a widely used label.

• A pivotal shift that expanded the community well beyond its original geographic focus.

• The reasoning behind uniting several regional insuretech groups under a single, national identity.

• How subtle changes in event design and content are influencing the direction of the InsurTech America Symposium.

• Why long-term value in insuretech still depends on relationships, shared learning, and consistent collaboration.

In this episode, Tracie Thompson, Global Head of Strategic Clients at Cytora, joins FNO: InsureTech to discuss how technology is transforming underwriting while preserving the essential role of human judgment. Drawing on her experience working with global insurers, Tracie explains how Cytora digitizes submission intake and enables underwriters to move away from fragmented data and manual processes toward faster, more consistent decision-making.

The conversation explores the realities of serving multinational insurance organizations, where technology adoption must balance standardization with local regulatory and operational complexity. Tracy also draws on her experience at AIG to share insights on leadership, resilience, and the importance of trust in complex market environments. Throughout the episode, she emphasizes that the future of underwriting lies in collaboration between advanced analytics and experienced human insight.

Key Highlights

• Tracy discusses Cytora's role in digitizing submission intake and underwriting workflows, enabling underwriters to synthesize large volumes of structured and unstructured data while reducing manual triage and administrative burden.

• The episode explores how Cytora operates as a platform within the underwriting ecosystem, supporting consistent decision-making across teams, regions, and lines of business.

• The conversation examines how global insurers navigate uneven regulatory frameworks and market conditions, requiring technology providers to balance standardization with local adaptability.

• Tracy draws on her experience at AIG to share insights on leadership, organizational resilience, and the importance of trust across insurers, clients, and partners in complex operating environments.

• The discussion looks at the practical realities of integrating AI into underwriting workflows, including adoption barriers, explainability, and cultural resistance. AI is positioned as a decision-support tool that enhances, rather than replaces, underwriter judgment.

• As experienced insurance professionals approach retirement, Tracy highlights the urgency of knowledge transfer and preserving institutional expertise. Technology can help capture and scale this knowledge, but human intuition remains central to complex risk decisions.

• The episode also addresses the insurance industry's branding and talent challenges, emphasizing the need to attract diverse, analytically minded professionals and reposition insurance as an innovative, impact-driven career.

Join us at ITC London, Jan 26 & 27 at The Brewery, to continue the conversation on underwriting innovation, AI, and the future of insurance. Secure your spot here

In this episode, Wesley Pergament, Co-Founder and CEO of Sola Insurance, joins FNO: InsureTech for an in-depth discussion on how Sola uses objective weather data and a hybrid policy model to address major pain points in property insurance. With roots in disaster recovery and technology, Wesley explains Sola's evolution from a tornado-focused product to comprehensive wind and hail coverage, targeting gaps left by high deductibles and widespread fraud. The conversation details Sola's careful expansion into 15 states through partnerships with vetted agency networks and ongoing engagement with organizations such as Lloyd's, both as coverholder and Lloyd's Lab participant.

Key Highlights

• Inspired by first-hand experience with Hurricane Sandy, Wesley describes Sola's foundation to help communities recover from natural disasters using data and engineering expertise.
• Sola started by offering tornado-specific parametric coverage before expanding to meet the scale of wind and hail losses, which together cause significantly higher annual damage than hurricanes or wildfires.
• Sola combines elements of parametric and indemnity insurance, optimizing for accurate, correlated loss response and aligning insurer and policyholder interests. The model leverages detailed weather analytics and property data in claim assessment.
• The company's core proposition is addressing the growing insurance gap as traditional home policies raise wind and hail deductibles—often above the cost of roof replacement. Sola's data-driven validation reduces exposure to opportunistic claims, supporting more efficient operations and sustainable loss ratios.
• Sola's claims are managed independently from primary carriers, typically settling within a few days after hail or wind events. The process relies on verified weather data, roof and property characteristics, and photographic evidence.
• Sola's selective agency strategy prioritizes established, reputable agents and sustained territory and account management support. The distribution approach focuses on quality representation and claims service excellence.
• Sola's participation in the Lloyd's Lab accelerator and current status as a Lloyd's coverholder have supported product development and reinsurance relationships. Product modeling draws from both proprietary analytics and leading catastrophe models (ISO/Verisk, RMS).
• State insurance departments, including Oklahoma, have highlighted Sola's program as a potential solution for homeowners facing increased premiums and limited wind and hail coverage.