Full Episodes | Insurtech Leadership Podcast

Inside the Underwriter’s Mind: How Sixfold AI is Redefining Risk, Speed, and Strategy

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 the founding team at Unqork, where she helped scale the no-code pioneer into a global enterprise before co-founding Sixfold.

Now, Jane is helping insurers harness AI to understand risk faster, more accurately, and with greater transparency. We’ll talk about how Sixfold is transforming underwriting from an art into a science, what “responsible AI” really means in insurance, and how Jane’s leadership philosophy—rooted in precision, empathy, and mentorship—is shaping an exciting InsurTech.

AI With Purpose: How Optalitix Is Turning Insurance Data Into Better Decisions

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, scalable applications—empowering actuaries, underwriters, and analysts to deploy AI at the heart of business workflows.

We’ll explore how Optalitix is helping insurers use AI responsibly to price risk, improve customer outcomes, and build smarter systems—and how Jon’s approach to leadership and technology has shaped one of the UK’s most innovative InsurTech success stories.

From Chaos to Clarity: How Ask Fetch Is Re-Wiring Agency Efficiency with AI

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 problems from the agency floor and translating them into intelligent automation. We’ll talk about how his team “21×-ed” their agency’s efficiency, the Garbage Can Theory that keeps operations sane, and what AI can realistically do today to help agencies scale smarter.

AI, Honesty, and Horsepower: How DriveX Is Modernizing Vehicle Inspections

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 leaving the desk.

Rauno calls himself a car enthusiast, metal-music fan, and role-playing-game guy—and his passion for both engineering and authenticity has shaped DriveX into one of Europe’s most agile “spartan” InsurTech teams.

We’ll talk about how DriveX is redefining trust between insurers and policyholders, where AI fits into the inspection process, and what it takes to keep a small, high-performing startup team firing on all cylinders.

Global Bridges for InsurTech Innovation: How InsurTech Israel Is Connecting Startups to the World

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 climate insurance, and helped elevate Israel’s position as one of the world’s leading InsurTech hubs.

We’ll talk about the new hubs launched in Guatemala and Slovenia, how InsurTech Israel is surfacing emerging founders from underrepresented markets, and what’s next for collaboration in the global InsurTech landscape.

Reinventing Home Insurance: Ty Harris on Building Openly and Scaling with Agents

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 economics and statistics at MIT and Northeastern, and began as a research assistant at Brookings. A Duke and MIT alum, Ty is a Fellow of the Casualty Actuarial Society (FCAS).

Rebuilding Insurance from the Ground Up: How Hover is Powering the Digital Claims Revolution with Ali Azhar

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" to founding and scaling tech companies, including ScholarshipExperts.com, and his pivot into software sales following an impactful business failure. His candid reflections offer valuable insights into resilience, reinvention, and leadership.

Ali also explains Hover’s groundbreaking technology, initially developed from military-inspired photogrammetry, and details how contractors "Trojan-horsed" Hover into the insurance industry. With over 10 million properties modeled, Hover's innovative approach significantly improves accuracy, reduces manual errors, and supports digital transformation across insurance and construction.

In This Episode:

• [02:19] Ali’s entrepreneurial roots and how overcoming business failure led to career reinvention.
• [11:33] Hover’s unique technology origin story and entry into the insurance market.
• [20:37] Why user experience and adjuster adoption are central to Hover’s growth.
• [22:40] Hover’s aggressive investment in innovation—allocating 50% of revenue to R&D.
• [25:33] The evolution of Hover’s interior claims automation from challenging beginnings to industry-leading solution.
• [29:39] Critical advice for insurtech startups: Be an innovation partner, not just a vendor.

Notable Quotes:

• “Insurance carriers are not technology businesses—they’re risk aversion experts. We have to meet them where they are.” [32:49]
• “The thing that always helped separate me from anyone else was I was willing to do more than what was asked.” [00:08:55]
• “Our bread and butter has been the exterior scoping solution. Over 10 years, we've modeled over 10 million properties.” [00:23:14]

About Our Guest:

 

Ali Azhar is a sales and business development leader with a proven track record of driving exponential revenue growth at companies like HOVER, GoodData, and MongoDB. A serial entrepreneur, he co-founded ventures like ScholarshipExperts.com and Velocity Athletics. Known for scaling teams, adding thousands of customers, and executing high-impact strategies, Ali combines hands-on startup experience with corporate leadership. He holds a degree in Management and Marketing from the University of North Florida and champions "altruistic capitalism" in business.

Resources:

Ali Azhar

• https://www.linkedin.com/in/aazhar/
• https://hover.to/

Josh Hollander

• https://www.linkedin.com/in/joshuarhollander/
• https://www.horton-usa.com/
• https://www.linkedin.com/showcase/insurtech-leadership-show/?viewAsMember=true
• https://www.insurtechassociation.org/
• https://innsure.org/

 

Data as Currency: Redefining Insurance with First-Party Intelligence with Elan Nyer

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, location, and vehicle condition—directly with insurers, creating a permissioned, transparent data marketplace. This shift not only improves underwriting and claims accuracy but also strengthens engagement between insurers and policyholders.

The conversation also dives into AI-driven verification, flexible integration models, and the larger opportunity to serve untapped, non-telematics users. Elan’s vision turns traditional data collection on its head—empowering individuals to own, protect, and profit from their digital footprint.

In This Episode:
[00:59] Elan’s background in automotive data and connected mobility
[03:01] The founding insight behind Ownli: data control and transparency
[05:00] Verified use cases: mileage, parking location, and condition check-ins
[09:35] Serving non-telematics users with valuable, self-reported insights
[12:06] Verifying user-submitted data with AI and 11-layer model architecture
[14:00] Ownli’s revenue-sharing model where users benefit from their data
[16:30] Three integration paths: SDK, web portal, and standalone app
[22:16] Building a verified “insurance profile” to streamline quoting and renewal
[30:12] Regulatory challenges and advocating for individual data ownership

 

Notable Quotes:

•  “If I had verified mileage and condition on my policy, my claim would have been resolved in 24 hours. Instead, it took months.” – Elan Nyer
• “Your data is an asset—just like money in a bank. We’re building the platform to help you own it, protect it, and earn from it.” – Elan Nyer

 

Our Guest:
Elan Nyer is the CEO and Co-Founder of Ownli, a platform that empowers consumers to share verified, first-party insurance data through a consent-first marketplace. Previously, he led teams at Mobileye and Nexar, focusing on automotive safety and connected vehicle intelligence.

 

Resources:

• Elan Nyer – LinkedIn | Ownli
• Josh Hollander –  LinkedIn | Horton International | Insurtech Leadership Show

Modernizing Claims: The Digital Future of Settlement Payments with Shannon Elsea

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 highlights the inefficiencies of traditional check-based settlements and explains how digital solutions can help both insurers and legal professionals streamline the final steps of the claims process.

They also explore how Settlement Done Easy bridges compliance and security requirements—like SOC 2 and NACHA—to address legal and ethical considerations. Shannon sheds light on what it takes to bootstrap a startup in insurance, the support he’s found in insurtech communities, and the potential to eventually offer same-day settlements.

 

In This Episode:

• [00:10] Introduction to Shannon - Shannon’s background as a personal injury lawyer and why he built Settlement Done Easy to cut down on payment delays.
• [00:49] The Real Cost of Paper Checks - Insight into why paper-based settlements are slow, prone to theft, and surprisingly expensive.
• [02:27] Paying Third-Party Claimants - How Settlement Done Easy addresses the compliance gap when sending funds to individuals, attorneys, and law firms.
• [07:04] Security at the Core - An overview of the platform’s SOC 2- and NACHA-compliant approach to safeguarding transactions.
• [18:34] Future of Same-Day Settlements- Exploring the potential for accelerating ACH timelines even further to meet market demand.
• [00:25:41] Bootstrapping a Startup - Shannon’s journey from idea to prototype, and how mentorship and startup communities provided essential support.

Notable Quotes

• [00:49] “We built Settlement Done Easy using current technology to replace the process of paper checks through the mail with an ACH payment.” – Shannon Elsea
• [02:27] “The challenge is, how do you pay the third-party claimant? How do you pay the represented claimant? And that’s where Settlement Done Easy comes into the mix.” – Shannon Elsea
• [11:54] “Over one billion dollars worth of checks are stolen out of the mail every year in the U.S.” – Shannon Elsea

 

Our Guest

Shannon Elsea is the founder of Settlement Done Easy, a digital platform that replaces mailed paper checks with secure ACH payments. Leveraging his 30+ years of experience as a personal injury attorney, Shannon aims to expedite insurance settlements and reduce risk for insurers and legal professionals alike.

 

Resources and Links

 

Shannon Elsea

 LinkedIn | Settlement Done Easy

 

Josh Hollander

 LinkedIn | Horton International | Insurtech Leadership Show

Transforming Insurance Finance: Treasury, Claims, and the Future of Payments with Curt Hess

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-time visibility over funds and streamline claims payments.

They explore how Vitesse’s technology addresses long-standing pain points, such as managing complex cash flows and reconciling accounts among multiple stakeholders. Curt explains how real-time insights, trusted fund management, and digitized settlements can enhance both operational efficiency and the policyholder experience. He also shares his perspective on leading cross-border teams, navigating market differences, and partnering with private equity.

Whether you’re an industry veteran or simply curious about the evolving landscape of insurance finance, this conversation provides an inside look at technology solutions reshaping treasury and claims processes.

 

In This Episode:

• [00:10] Introduction to Curt Hess - Meet the U.S. Executive Vice President of Vitesse and learn why his banking and treasury background fuels the company’s expansion strategy.
• [02:38] Real-Time Fund Visibility - Curt explains how Vitesse’s unified technology platform offers insurers real-time insights on fund flows, improving operational efficiency.
• [06:51] The “Last Mile” of Claims Payments - How Vitesse enables policyholders to choose their preferred payment method and reduces claim settlement times from weeks to hours.
• [10:40] Addressing Long-Standing Pain Points - A look at how historic inefficiencies—like scattered funds and time-consuming reconciliations—are being tackled with new solutions.
• [14:40] Navigating U.S. Market Differences - Key learnings from adapting a UK-born platform for the American insurance landscape, including regulatory nuances and client feedback.
• [25:34] Collaboration with KKR - Curt highlights Vitesse’s partnership with private equity firm KKR and how it supports the company’s strategic initiatives and growth.
• [28:24] The Industry’s Future - Curt’s perspective on how insurers are modernizing financial workflows in response to factors like inflation, natural disasters, and rising customer expectations.

 

Notable Quotes

• [00:07:31] "The last thing that a policyholder wants at the time of need is to worry about where their claim is and how they are going to get paid." – Curt Hess
• [00:20:06] "Bringing people over is super important because unless they come over and experience it, they really may not quite understand some of those differences that need to be addressed." – Curt Hess
• [00:23:31] "It's really important that the culture in Vitesse across the pond is the culture we want to build here in the U.S., around having humility, driving to succeed, and ultimately having a real client focus." – Curt Hess
• [00:28:24] "The industry is having to adapt with a number of headwinds, whether it's natural disasters, inflation, or social inflation driving things up with legal and court verdicts." – Curt Hess

 

Our Guest

Curt Hess is the U.S. executive President of Vitesse, a global treasury and payment solutions provider specializing in the insurance industry. With a background in banking, he brings extensive experience in financial services. At Vitesse, Curt focuses on expanding operations, particularly in the U.S., and enhancing client-centric solutions for efficient claims processing and treasury management.

 

Resources and Links

 

Curt Hess

• https://www.linkedin.com/in/curt-hess-81425251
• https://www.vitesse.io/

 

Josh Hollander

• https://www.linkedin.com/in/joshuarhollander/
• https://www.horton-usa.com/
• https://www.linkedin.com/showcase/insurtech-leadership-show/?viewAsMember=true