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The Insurtech Leadership Podcast

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

  1. MAR 5

    Why 90% of AI Pilots Stall (And How to Escape Pilot Purgatory)

    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, owned a $150M P&L, and delivered transformations that only happen when you understand how work actually moves—handoffs, exceptions, controls, and accountability. At Appian, he leads the insurance vertical for a process automation and low-code platform focused on claims, underwriting, and operational process orchestration. Key Topics • Pilot Purgatory: Why 90% of AI Projects Stall — Pilots work in controlled environments. Then reality hits: no data pipeline, no workflow integration, no governance, no frontline buy-in. Organizational alignment—not technology—is the breaking point. • The Orchestration Layer — Appian's core thesis: build an orchestration layer first. It sits between your legacy monolith and the next chapter. Additive, keeps work flowing during transformation, and creates the foundation where AI and automation actually stick. • Email as Infrastructure — Underwriters spend 40%+ of their day in inboxes. The AI mailbox use case embeds AI into a workflow that extracts data, routes work, makes decisions, and triggers actions. Underwriters gain 2–3 hours a day back. • Claims Velocity: Days to Hours — One global insurer went from 24–72 hours (FNOL to assignment) to minutes. Digital intake feeds orchestrated workflows. AI triages, categorizes severity, flags fraud risk. The adjuster gets a complete, pre-organized package. • Alignment = Culture, Not Just Tech — Appian's workshops put business, IT, data, and operations in one room to design the ideal state and work backward. Underwriters don't get replaced—they become superhuman. Admin work gets stripped away. • The Talent Problem Is a Workflow Problem — Entry-level insurance work is repetitive email categorization. When AI handles the mundane, these jobs become analytical and attractive again. The organizations winning reskill existing teams and position domain expertise as more valuable. • The 90-Day Deployment Mindset — Pick one workflow. Build the orchestration layer. Plug in AI. Show ROI in 90 days. Then iterate. Key Quotes -"When you go to scale it, it's like, well, we don't have the data pipeline. We don't have the workflow. We don't have the governance. We don't have the buy-in from the frontline team. And so it just stalls." -"It's not about the AI itself. It's about the workflow that the AI sits inside." -"We're not here to replace underwriters. We're here to make them superhuman." -"Get started. Don't let perfect be the enemy of good. Start with a use case, build the orchestration layer, plug AI into it, show value in 90 days." Resources • Appian: appian.com • Jake Sloan LinkedIn: https://www.linkedin.com/in/jacobpsloan] • Joshua R. Hollander, Host: https://www.linkedin.com/in/joshuarhollander/ • Horton International: https://www.horton-usa.com/ Subscribe & Follow Never miss an episode. Subscribe on Spotify, Apple Podcasts, YouTube. Follow the show on LinkedIn: https://www.linkedin.com/showcase/insurtech-leadership-show #InsurTech #Insurance #InsuranceInnovation #FutureOfInsurance #ExecutiveLeadership Subscribe & Follow Never miss an episode. Subscribe on your favorite podcast platform—Spotify, Apple Podcasts, YouTube. Follow the show on LinkedIn: https://www.linkedin.com/showcase/insurtech-leadership-show #InsurTech #Insurance #InsuranceInnovation #FutureOfInsurance #Leadership #ExecutiveLeadership

    32 min
  2. MAR 4

    API-First Insurance: When Brands Become Insurers

    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 of credit cards"—building the rails for digital insurance distribution. Key Topics 1. What "Digital Insurance" Really Means Digital insurance is not about moving forms online or replacing phone calls with web interfaces. True digital insurance is straight-through processing from quote to policy issuance to payment—mirroring the speed and frictionlessness of e-commerce transactions. Wayne explains: "If that transaction requires some asynchronous process, some process that is interrupted, that we are actually not doing digital insurance." The benchmark: the entire process happens within minutes, not days or weeks. 2. API-First Infrastructure vs. Legacy Core Systems Sure's platform differs fundamentally from monolithic core policy administration systems (like Guidewire or Duck Creek) because it was built API-first with data normalization at its foundation. Legacy cores encourage over-customization, which locks insurers into inflexible, non-compliant systems. Sure's approach standardizes policy data across product types (homeowners, renters, fine art, landlord), enabling rapid changes and integrations. Unlike legacy systems, Sure doesn't force carriers to choose between their existing tech and innovation—it coexists alongside legacy infrastructure. 3. Model Context Protocol (MCP) and AI Agent Integration In February 2026, Sure announced the industry's first MCP server integration, enabling Claude AI agents to interact directly with Sure's infrastructure. MCP is a standardized protocol that allows AI agents to connect to business systems without custom integrations for each use case. This means insurers and brands no longer need 6-12 months of engineering to embed insurance; AI agents can quote, bind, manage, and renew policies conversationally. 4. Why Non-Endemic Brands Will Build Insurance The next major insurance distributors won't be insurance companies. They'll be brands, e-commerce platforms, fintechs, and technology companies with massive customer bases. Wayne's economic thesis: if a brand can convert customers to insurance at 20-30x the typical rate (vs. giving customer data to a third party), the unit economics change entirely. Large brands now have a path to retain customers and data while building insurance revenue. 5. The Transaction Layer as Moat Insurance isn't like retail or travel—regulatory consequences are real, policy admin systems are complex, and compliance layers must operate end-to-end. Sure's competitive advantage lies in building the foundational transaction layer that carriers either cannot replicate internally or would take years to engineer. This infrastructure layer is what enables AI agents to work reliably within compliance and regulatory constraints. 6. Insurance as an Ecosystem The future isn't a single insurer offering multiple products—it's an ecosystem where brands, platforms, and technology companies collaborate on insurance delivery. AI agents, powered by Sure's infrastructure, enable this distributed, composable insurance ecosystem. Key Quotes -"What digital insurance really means is truly a straight-through process where you're starting to get a quote that quote will be a real quote. It's not an estimate. It will become a real policy. You will pay real money. You will get a real coverage document. And the timing of all of that is pretty close to what you expect from regular old e-commerce." -"The next big insurance distributors won't be insurance companies. They will be brands. They'll be technology companies. They'll be fintechs. They'll be AI companies. They'll be companies that are currently sitting on large customer bases that don't have insurance products today." -"Before MCP, if an AI agent wanted to interact with an insurance system, you'd have to build a custom integration for each system, each use case. MCP standardizes that." Resources • Sure: https://sure.com • Wayne Slavin LinkedIn: https://www.linkedin.com/in/wayneslavin • Horton International: https://www.horton-usa.com/ Subscribe & Connect Tune in to the Insurtech Leadership Podcast for deep-dive conversations with insurance executives, founders, and innovators shaping the future of insurance technology. • LinkedIn: https://www.linkedin.com/in/joshuarhollander/ • Podcast Showcase: https://www.linkedin.com/showcase/insurtech-leadership-show #InsurTech #Insurance #InsuranceInnovation #Innovation #FutureOfInsurance #Leadership #ExecutiveLeadership

    31 min
  3. FEB 27

    No Fault, No Claims Adjuster, No Friction: Randel Bennett on the Future of Guarantees

    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 is CEO and co-founder of Qixent, a Chicago-based insurance exchange platform and licensed MGA enabling carriers and partners to launch and distribute insurance products at speed and scale. Randel's insurance career spans traditional carriers (Allstate in product management), startup ventures (co-founder of Sigo Seguros, focused on non-standard auto for Hispanic buyers), and reinsurance infrastructure (VP of Strategic Partnerships at Swiss Re, working with dozens of MGAs and insurtechs on alternative distribution and new product development). He is currently pursuing an MBA from the University of Chicago Booth School of Business and holds a degree from Florida International University. Key Topics No-Fault Embedded Insurance: From Blame to Guarantee Traditional insurance asks: "Whose fault was it?" No-fault embedded insurance removes the blame entirely. By embedding a parametric trigger (a predefined event and payout) directly into a service or product, you convert insurance into a guarantee. When solar panels underperform due to weather, the data triggers an automatic payout—no claims adjuster, no friction. The customer gets paid faster; the carrier transfers weather risk cleanly. Data as the Foundation of Underwriting The critical edge in performance guarantees is determining expected production with precision. Qixent uses weather data, historical production records, satellite imagery, and panel specifications to establish a baseline for each project. This data-first approach allows predictable, sustainable pricing and removes the guesswork from underwriting. As Randel notes, "data is really the core of everything that we do." Annual Reconciliation vs. Event Triggers Qixent's model allows flexibility: real-time payouts for significant weather events, but the dominant approach in commercial solar is annual reconciliation. Over a 12-month period, Qixent compares actual production to expected production. If weather caused a shortfall, the guarantee covers the gap. For 20–25 year projects, this cadence keeps both sides—EPC and asset owner—on stable, predictable footing. From Commercial Solar to the Energy Transition Qixent's 3–5 year vision extends beyond commercial solar into residential solar, battery storage, EV charging, and fleet electrification—any space where a performance obligation faces weather, grid reliability, or supply chain constraints. The underlying infrastructure is designed to be vertical-agnostic: "If we can measure it, we can guarantee it." Founder Lessons: Humility, Problem-Market Fit, Co-Founder Complementarity Randel's advice to insurance professionals considering entrepreneurship: Lead with humility (startup resources are scarce; you become the team). Solve a real, unmistakable problem (the performance guarantee gap in clean energy was Randel's unsee-able insight). Find a co-founder who complements your blind spots (Randel brings insurance and relationships; Glenn brings technology and operational rigor). And protect work-life balance—burnout tanks companies faster than capital constraints. Notable Quotes • "In the no-fault embedded space, we're removing the blame entirely... When their solar panels underperform due to weather, for instance, the data says, hey, this is what happened. And that triggers a payout. And that's it." • "Data is really the core of everything that we do... because of that, we can price it in a way that's affordable and sustainable for the long term." • "We're not just a tech company. We're an insurance company that uses technology. And that distinction matters." • "When you come from a large organization, you're used to having resources at your disposal... When you go to a startup, you are the team. You are the infrastructure. And that requires a level of humility that a lot of people aren't prepared for." • "If we can measure it, we can guarantee it. That's the big vision." Resources & Links • Qixent: https://qixent.com/ • Randel Bennett LinkedIn: https://www.linkedin.com/in/randeljb/ • Randel Bennett Email: randel@qixent.com • Horton International: https://www.horton-usa.com/ • Joshua R. Hollander LinkedIn: https://www.linkedin.com/in/joshuarhollander/ • Insurtech Leadership Podcast Showcase: https://www.linkedin.com/showcase/insurtech-leadership-show Subscribe & Follow New episodes drop weekly. Subscribe to the Insurtech Leadership Podcast on Podbean and YouTube. Follow Joshua R. Hollander on LinkedIn for episode updates, clips, and industry commentary.

    29 min
  4. FEB 25

    Consolidation Without Chaos: How ALKEME Integrates and Grows at Scale

    Introduction In this episode of the Insurtech Leadership Podcast, host Joshua Hollander sits down with Curtis Barton, CEO and founding visionary of ALKEME Insurance, to explore how ALKEME built one of the fastest-growing brokerage platforms in the country - not by outspending the competition, but by out-integrating them. Curtis shares the unconventional origin story behind ALKEME, his philosophy on alignment, and why firms that invest in people, systems, and technology will define the next era of insurance distribution. Guest Bio Curtis Barton is CEO and founding visionary of ALKEME Insurance. He began his insurance career in 1996 and founded Venture Pacific Insurance, a regional brokerage in Southern California, before co-founding Brokkrr, a digital lead generation insurtech platform. Curtis orchestrated the complex merger of seven independent agencies to form ALKEME, championing a people-powered, tech-enabled business model. Under his leadership, ALKEME has grown to a top-25 brokerage with over 1,000 employees across 50+ locations nationwide. Key Topics • Integration-first vs. rapid roll-up - Why ALKEME chose to build a unified platform from day one rather than stack EBITDA through fast acquisitions, and how that decision shapes every partnership conversation. • One class of stock, true alignment - ALKEME issues a single class of equity to every partner - no preferred, no investor stock. Curtis explains why this structure is the foundation of cohesive alignment. • The compression problem in brokerage multiples - How the spread between entry and exit multiples has collapsed, creating liquidity risk for agencies that relied on financial engineering over operational improvement. • Why agency owners join (not sell) - Most principals aren't looking for exits - they're looking for resources, technology, and scale they can't build alone. ALKEME's pitch is about what changes after close. • SOPs, systems, and reinvestment as growth levers - How deploying standardized processes and technology into historically under-resourced agencies unlocks organic growth at the producer level. • AI as augmentation, not replacement - ALKEME's approach to AI: position producers to be the most valuable asset in the transaction by giving them better tools, not replacing them with automation. • Building leadership that scales - Why Curtis believes no one is a "forever employee" and how ALKEME constantly evolves its leadership to match the company's growth trajectory. Quotes • "We just decided to do our own thing and do it differently. We ended up recruiting nine of my friends out of a cluster that we were all part of that had their own agencies." • "One dollar of organic can give you seven of inorganic capacity, and you've got to look at it from that perspective." • "There is no preferred, there is no investor stock. They have the same exact share that I have that any of our partners have. And that's called alignment." • "Most of these people don't want to sell their agency. They just know that they're going to get outscaled and out-resourced." • "We were already edging towards a people-powered, tech-enabled business, and we talk constantly about how do we position our people to be the most valuable asset in the transaction." Resources • ALKEME Insurance: alkemeins.com • Curtis Barton on LinkedIn: linkedin.com/in/curtis-barton-8103682/ Subscribe & Review If you enjoyed this episode, subscribe to the Insurtech Leadership Podcast on YouTube, Apple Podcasts, Spotify, or wherever you listen. Leave a review - it helps other insurance and technology professionals find the show.

    32 min
  5. FEB 20

    Auto Insurance: Stabilizing or Stuck?

    Introduction In this episode of the Insurtech Leadership Podcast, host Josh Hollander sits down with Gemma Ros, CTO at The Zebra, to unpack their 2026 State of Auto Insurance Report. They explore what's driving premium divergence across states, how affordability pressure is reshaping consumer behavior, and where regulation, loss costs, and distribution dynamics collide. Guest Bio Gemma Ros is CTO at The Zebra, one of the largest insurance comparison platforms in the United States. Born in Spain, Gemma built her career across engineering and data roles before joining The Zebra, where she leads the technology organization responsible for data infrastructure, product engineering, and AI capabilities. She brings a unique perspective as both a technologist and an insurance industry insider who sees real-time consumer shopping behavior at scale. Key Topics • State-by-state premium divergence — Auto insurance premiums are not stabilizing uniformly. Regulatory environments, loss cost trends, and competitive dynamics are creating vastly different realities depending on where you live. • Affordability pressure and coverage erosion — Consumers facing higher premiums are choosing higher deductibles, lower coverages, and state minimums — creating knock-on effects for uninsured/underinsured motorist exposure across the market. • Carrier growth signals in ad spending — When carriers increase advertising, it signals growth appetite and competitive pricing — a cue for consumers to reshop their policies. • Rate filing dynamics — New rates are being filed and going into effect daily, making the market a moving target for both consumers and distribution partners. • Telematics and ADAS impact on underwriting — Usage-based insurance and advanced driver assistance systems are beginning to reshape how risk is priced, though widespread impact is still unfolding. • Autonomous vehicles and insurance implications — The shift from driver liability to product/manufacturer liability as autonomy scales, and what that means for carriers. • Taking AI from fun to material impact — Gemma's 2026 engineering theme: moving AI adoption from experimental to scalable, repeatable, and operationalized across the entire engineering organization. Quotes • "It's never a bad idea to shop around. Educate yourself — you might be leaving money on the table." • "If you start seeing a lot more ads for insurance companies on TV or on podcasts, that's a good time to reshop — the carriers are signaling they want to grow." • "My main theme for 2026 is taking AI from fun to material impact." Resources • The Zebra's 2026 State of Auto Insurance Report: Available at thezebra.com • The Zebra: thezebra.com — insurance comparison platform Subscribe & Review If you enjoyed this episode, subscribe to the Insurtech Leadership Podcast on YouTube, Apple Podcasts, Spotify, or wherever you listen. Leave a review — it helps other insurance and technology professionals find the show.

    32 min
  6. FEB 13

    Live Maps, Smarter Risk: Inside TomTom’s Insurance Playbook

    -Introduction TomTom isn’t just “navigation” anymore. In this episode of the InsurTech Leadership Podcast, Josh Hollander talks with Vinod Poomalai, Head of InsurTech Product Marketing at TomTom, about how insurers are using location, map, and traffic intelligence to improve how they price risk, validate claims, and build telematics programs that actually produce underwriting signal. Guest bio Vinod Pumalai leads go-to-market for TomTom’s insurance and InsurTech vertical. His work focuses on helping carriers, brokers, actuaries, and InsurTech teams integrate TomTom’s location and traffic data into risk models, pricing engines, and telematics workflows—with a practical emphasis on adoption inside real operating environments. Key topics -From static territories to live location intelligence -Why “territory” is a crude proxy—and how mobility patterns add resolution to risk. -Territory risk models powered by traffic + map data -How insurers use location and traffic attributes to refine pricing and portfolio strategy. -Telematics enablement: APIs, SDKs, and flexible integration -What teams actually plug into, and what the implementation path looks like in practice. -Claims validation and fraud detection using mobility history -Using historical mobility/traffic context to validate events faster and reduce leakage. -Where experimentation becomes operational value -The difference between demos and workflows that move loss ratio outcomes. -What the insurance market is missing in location data -Why the market has been underserved—and what that creates as an opportunity. -Talent and leadership required to make it real -Product, data, and insurance domain collaboration: what “good” looks like inside carriers. Quotes -“The insurance market as a whole is very underserved when it comes to location data, traffic data, and so on.” -“At the end of the day, what our clients really care about… is loss ratios.” -“Customers are leveraging our traffic data in validating auto insurance claims.” Resources -Vinod Poomalai: https://www.linkedin.com/in/vinod-kumar-poomalai/ -TomTom Insurtech: https://www.tomtom.com/solutions/insurtech/ -Joshua Hollander: https://www.linkedin.com/in/joshuarhollander/ If you found this useful, subscribe to the InsurTech Leadership Podcast on YouTube and your preferred podcast app. Share the episode with an underwriting, claims, or telematics leader on your team—and leave a review to help more operators find the show.

    29 min
  7. FEB 11

    Beyond Chatbots: How Cara Becomes Your Best CSR

    Introduction “AI in insurance” has become shorthand for chatbots and generic automation. This episode focuses on a more operational question: what would it take for AI to behave like a dependable CSR inside a real agency workflow — completing service work end-to-end, without eroding trust or the customer experience? Guest Bio Nikhil Kansal is the Co‑Founder & CTO of Cara, a domain‑specific AI platform built for insurance to automate servicing and assist with sales. Prior to Cara, Nikhil co‑founded Oyster, a digital brokerage built around customer experience and risk placement. Earlier in his career, he worked as an infrastructure engineer at Stripe, helping operate global payments at high reliability. Key Topics (with context) -Beyond “chatbots” to an AI CSR: Why the bar is task completion, not conversation quality. Delegation + trust: What changes when AI becomes a coworker you can assign work to (and verify). -System-of-record reality: How Cara is designed to sit on top of existing tools instead of forcing a rip-and-replace. -Agency workflow fit: Where service volume lives (certificates, policy changes, routine requests) and what can be automated safely. -Voice + email automation: The operational implications when AI can handle phone calls and inbox-driven work. -Cost control vs service expectations: How leaders reconcile staffing constraints with rising customer expectations. -Guardrails + change management: What “safe automation” looks like in regulated, high-trust environments. Quotes -Nikhil: “It’s a coworker that you can delegate certain tasks to — and you can trust that it gets completed end‑to‑end.” -Nikhil: “Cara is not a replacement for an AMS; it’s more of a coordinator on top of your system of record.” -Nikhil: “Cara can pick up the phone, speak to the customer, and understand what they’re calling about.” Resources Mentioned Nikhil Kansal: https://www.linkedin.com/in/nikansal/ Cara: https://www.getcara.ai/ Joshua Hollander: https://www.linkedin.com/in/joshuarhollander/ If you lead service, ops, or growth at an agency, MGA, carrier, or insurtech: subscribe for operator-level conversations. - Follow/subscribe on YouTube - Subscribe on your podcast platform (Apple Podcasts, Spotify, Podbean, etc.) - Share the episode with the colleague who owns service capacity and staffing plans

    28 min
  8. FEB 6

    Rewriting MedMal with AI: Inside Indigo (with Jared Kaplan)

    Medical malpractice is one of the most established specialty lines—and one of the hardest to modernize. In this episode of the InsurTech Leadership Podcast, Joshua Hollander sits down with Jared Kaplan, Co‑Founder & CEO of Indigo Technologies, to unpack why MedMal is finally ready for a different underwriting and distribution model. Indigo’s bet: you can make MedMal dramatically easier for physicians and brokers without relaxing underwriting discipline—by replacing slow, form-heavy workflows with alternative data, machine learning, and tight operational execution. Guest Bio Jared Kaplan is the Co‑Founder and CEO of Indigo Technologies. Indigo is rethinking medical malpractice insurance with an approach that combines broker-friendly distribution, faster quoting, and underwriting models informed by large-scale claims data and alternative data signals. Key Topics -Why MedMal is “built to resist change”: entrenched processes, long feedback loops, and the real cost of underwriting mistakes. -Underwriting without an application: what replaces the traditional intake and how you maintain discipline. -Alternative data in a high-stakes line: how Indigo uses a broad feature set (beyond prior claims history) to improve risk selection. -Risk segmentation and value creation: lowering premiums for the “overpaid” majority while avoiding the concentrated loss drivers. -The 80/20 claims reality: the small portion of physicians that drives a disproportionate share of MedMal claims. -Brokers as the distribution partner of the future: what modern carriers/MGAs must do to earn broker trust and share. -Operating model over buzzwords: where the real leverage is—quote speed, workflow simplicity, and consistency. Quotes -Jared: “We started with the premise that you don’t need an application.” -Jared: “I would argue Indigo is the baby of both… online distribution… and underwriting using alternative data and machine learning.” -Jared: “There’s no one else there that can figure out the twenty percent of docs that are driving sixty percent of the claims.” Resources Indigo Technologies (company site): https://www.getindigo.com/ Jared Kaplan (LinkedIn): https://www.linkedin.com/in/jared-kaplan-683412/ If you work in specialty insurance, broker distribution, MGAs, or underwriting modernization, this one is a pragmatic look at where AI actually earns its keep. Subscribe for more operator-grade conversations on insurtech, insurance innovation, and leadership—and if you found value here, leave a review to help more executives discover the show.

    30 min
4.4
out of 5
21 Ratings

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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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