Full Episodes | Insurtech Leadership Podcast

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 o...

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...

-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 Vin...

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...

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 phy...

Introduction Josh Hollander sits down with Vishal Sankhla, Co‑Founder & CEO of OutMarket, to get specific about what “AI in insurance” looks like when it actually changes operations. The focus is commercial insurance workflows—where work still runs through email, PDFs, spreadsheets, and agency management systems—and how to cut cycle time and errors without creating new risk. Guest bio Vishal S...

Most "core modernization" programs fail for one boring reason: fragmentation. Not the tech. The contract sequencing, the handoffs, the Excel that becomes the unofficial system of record-and the silent operational risk that follows. If you're still running underwriting, claims, billing, and reinsurance as separate truths, you're not modernizing. You're just integrating failure modes. Rob Lewis, CEO...

Claims ops keeps buying “automation” that quietly adds work: more review, more disputes, more cycle time. The real villain is verification overhead—when you still have to check everything, “80% automated” is a new cost center disguised as progress. Ralph von Grafenstein, Founder/CEO, DocuSketch, has lived the messy middle of property claims: documentation fights, estimate friction, and payout dela...

Most claims “AI programs” die the same way: you buy models, bolt them onto core, and discover your data can’t support event-driven decisions. The result isn’t bad predictions—it’s diary-driven claims, slow closes, reserve noise, and a false sense of progress. Heather Wilson (CEO) and Mubeen Rabbani (CPO) at Clara Analytics have lived this at scale: thousands of claims triaged daily, with alerts ti...

Insurance isn’t short on “AI demos.” It’s short on AI that actually survives real workflows—submissions, audits, claims intake, policy comparison, compliance. Aman Gour (CEO, FurtherAI) breaks down what agentic AI actually means in practice, why “accuracy you can trust” is the real moat, and how teams move from one automated workflow to a platform-wide operating layer. What you’ll hear (high-signa...

"Best-of-breed” feels like the sophisticated choice—until you try to run a scaled brokerage platform on it. The failure isn’t theoretical: inconsistent data, fragile integrations, impossible governance, and post-close execution drift. That’s where value leaks—quietly, expensively, and usually after the deal is already signed. I’m going live with Trevor Bunker, Chief Customer Officer, Applied Syste...

When fraud pressure rises, carriers tighten controls. The hidden cost: cycle time balloons, adjusters burn out, and your best customers feel like suspects. That’s how you leak value—quietly—over quarters. In this episode of the Insurtech Leadership Podcast, host Joshua R. Hollander speaks with Clearspeed's CEO Alex Martin about how his view that the fix isn’t “better fraud analytics.” It’s a trust...

AI Won’t Fix Intake Without an Operating Model

Today on The InsurTech Leadership Podcast, we’re joined by Jane Tran, Co-founder and Chief Operating Officer of Sixfold AI—a fast-growing InsurTech that’s reimagining the underwriting process through the practical use of artificial intelligence. Jane’s journey started on Wall Street at JP Morgan, followed by leadership roles in strategy and innovation at Marsh and MetLife. She then became part of...

Today on The InsurTech Leadership Podcast, we’re joined by Jonathan Shapiro, Co-founder and Director of Optalitix, a company transforming how insurers and financial services organizations make data-driven decisions. Jon’s background uniquely bridges software engineering, AI innovation, and entrepreneurial leadership. At Optalitix, he’s helped build a platform that turns data models into live, scal...

Today on The InsurTech Leadership Podcast, we’re joined by Trace Meek, a third-generation insurance agency owner turned tech innovator and the CEO of Ask Fetch. After years of battling endless PDFs, Excel files, and underwriting emails, Trace built Ellie AI—a conversational assistant that can answer carrier underwriting questions in seconds. Trace’s story is one of pure practicality: taking real p...

Today on The InsurTech Leadership Podcast, we’re heading to the intersection of automotive technology, AI, and user experience with Rauno Sigur, CEO and Co-Founder of DriveX Technologies. DriveX is an Estonia-based startup using AI-driven image recognition and remote-inspection tools to help insurers, leasing companies, and fleet managers verify vehicle condition instantly—without an adjuster ever...

Today on The InsurTech Leadership Podcast host Joshua Hollander speaks with Kobi Bendelak, Founder and CEO of InsurTech Israel—a global ecosystem builder connecting startups, investors, and insurers from over 50 countries. Under Kobi’s leadership, InsurTech Israel has launched multiple international innovation hubs, built a global accelerator that’s produced standout startups in AI, cyber, and cli...

Ty Harris is CEO and co-founder of Openly, a VC-backed startup reinventing homeowners insurance for independent agents. Before founding Openly in 2017, Ty co-founded Quote Hopper and spent 12+ years at Liberty Mutual, where he rose to EVP & Chief Product Officer overseeing $18B in premium across Liberty and Safeco brands, plus $3B across 17 countries. Earlier in his career, he lectured in econ...

In this episode of the Insurtech Leadership Podcast, host Joshua Hollander speaks with Ali Azhar, Chief Business Development Officer at Hover, a leading prop-tech and insurtech company leveraging advanced AI and 3D spatial data to streamline property assessments and claims processes. Ali shares his remarkable personal journey—from childhood entrepreneurial efforts driven by "altruistic capitalism"...

What if insurance data weren’t just extracted—but earned? In this episode of the Insurtech Leadership Podcast, host Josh Hollander sits down with Elan Nyer, CEO and Co-Founder of Ownli, to explore how policyholders can take control of their data and become active participants in the insurance value chain. Elan shares how Ownli enables consumers to share verified, first-party data—such as mileage,...

In a world where digital transactions are the norm, why are many insurers still processing paper checks for claims settlements? In this episode of the Insurtech Leadership Podcast, host Josh Hollander talks with Shannon Elsea, founder of Settlement Done Easy, about bringing a faster, more secure approach to third-party claims. Drawing on his 30 years as a personal injury attorney, Shannon highligh...

The insurance industry faces mounting challenges to simplify financial operations and deliver fast, seamless claim payments. In this episode of the Insurtech Leadership Podcast, host Joshua Hollander talks with Curt Hess, U.S. Executive Vice President of Vitesse, about how the company’s treasury and payment platform helps insurers, managing general agents, and third-party administrators gain real-...

Commercial insurance is a billion-dollar industry—but behind the scenes, it’s a mess. Agents are buried in outdated processes, struggling to keep up with client needs and fighting to prove their value in a system that just isn’t built for efficiency. So, what if there was a better way? What if technology could finally give agents the tools they need to move beyond paperwork and actually reduce ris...

In this episode of the Insurtech Leadership Podcast, host Josh Hollander welcomes Nakita Devlin, CEO and Co-founder of Ric, who shares how her company is democratizing parametric insurance products for everyday Americans. Unlike traditional catastrophe coverage, Ric's approach focuses on immediate, predefined payouts triggered by meteorological events rather than complex damage assessments.   Devl...