Full Episodes | Insurtech Leadership Podcast

Introduction

Every insurer receives risk submissions the same way: an email arrives, packed with documents in whatever format the broker chose to send them, and someone on the operations team has to figure out what is in there. The problem is not that carriers lack data. The problem is that nobody has built a scalable way to operationalize it. Richard Hartley spent a decade building that infrastructure at Cytora — and then sold it to the company that reaches seventy percent of US agents.

Hartley is the co-founder and CEO of Cytora, an AI-powered risk processing platform acquired by Applied Systems and now powering EPIC Autofill and EPIC Submissions Manager. The conversation was recorded live at AppliedNet, where Cytora's integration into the Applied ecosystem was being unveiled. In this conversation, Josh Hollander and Hartley dig into how Cytora's seven-agent architecture produces confident extraction from any document format, why automation is a dial not a switch, and what it took to rebuild the company from ninety people to thirty at the start of COVID before finding the right product.

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Guest Bio

Richard Hartley is the co-founder and CEO of Cytora, an AI-powered risk processing platform now operating as a division of Applied Systems. Cytora digitizes and processes risk submissions across any format — emails, PDFs, spreadsheets, images — and routes structured data into downstream systems including policy admin, underwriting platforms, and agency management systems. Before founding Cytora, Hartley studied history and political science, worked in Shanghai for a tech company building core insurance systems across Asia Pacific, and trained as a classical ballet dancer. Cytora's technology is now embedded in EPIC, Applied's core agency management system used by seventy percent of US agents.

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Key Topics

The problem was never too little data

Cytora's original thesis was that underwriters needed more data to make better risk selection decisions. That turned out to be wrong. The real problem was that carriers could not operationalize the data they already had into a workflow that functioned at scale. Recognizing that distinction forced a full company pivot — and ultimately led to the product that Applied acquired.

Be agnostic to the input, define the output

Most earlier attempts to digitize submissions trained models on labeled examples of prior submissions — a rigid approach that broke every time document formats changed. Cytora took the opposite position: be entirely agnostic to what comes in, whether it is a bare email, a long Excel spreadsheet, a set of images, or a stack of PDFs, and instead let the insurer define their view of risk as the output. That design principle became the foundation of a platform that works across every line of business without retraining.

Seven agents at different temperatures

Cytora's extraction engine runs seven AI agents simultaneously on the same field, each using a slightly different strategy. When all seven return the same value, confidence is high and the field is accepted automatically. When agents disagree, confidence drops and a human review task is triggered. It is the same logic as solving a math problem seven different ways — agreement across methods is the confidence signal.

Automation is a dial, not a switch

Carriers and insurers sit at different points on the automation spectrum. Some will route lower-complexity, homogeneous risks straight through without human review. Others will use Cytora to present every risk decision-ready but keep a human in the final approval seat. Hartley is deliberately non-prescriptive about which is right — the platform accommodates both, and the correct setting depends on risk complexity, organizational strategy, and appetite for accountability.

The Applied acquisition: emotionally as much as analytically

Cytora was raising its Series C when it met Applied at a conference. Both organizations had been solving the same problem from different ends of the value chain — Cytora from the insurer side, Applied from the broker and agent side. Hartley describes the acquisition decision as emotional as much as analytical: seventy percent of US agents use Applied, which made joining forces the only path to the scale of industry impact Cytora was built to achieve.

EPIC Autofill and what comes next

Post-acquisition, Cytora integrated into EPIC via API in a matter of weeks. Documents that agents previously had to read, review, and rekey manually are now digitized automatically and pre-populated in EPIC. Coming next is a feature called Transactions — a capability that unifies the multiple follow-up communications that typically accompany a single submission into one coherent, complete risk view for the insurer.

Founder lesson: be obsessed by the problem, not the solution

Cytora's hardest moment came at the start of COVID, when the team pivoted from ninety people to thirty with no certainty about what the new product would be. Hartley's advice to founders in that position: stay obsessed with the problem. The solution will come if the problem is real and you care enough about solving it. Hire people who show commitment under pressure rather than people who describe what they would do in theory.

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Notable Quotes

"The reason we exist is really to enable risk to flow in a much more frictionless way through the value chain, from the retail broker through to the insurer."

"Be agnostic to the input because you can't control it. But define the output you want. Define your view of risk."

"I view automation as a dial. You should dial it up, dial it down, really depending on what your strategy is and what you're trying to do."

"We went from eighty, ninety people to around thirty people. We had no idea what the product would be that we would build."

"Be obsessed by the problem. Don't worry about not knowing the solution, because it will take some time."

"Seventy percent of agents in the US use Applied. Being intellectually honest, that was the path."

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Resources

Guest:
Cytora: https://www.cytora.com
Applied Systems: https://www.appliedsystems.com
Richard Hartley on LinkedIn: https://www.linkedin.com/in/richard-hartley-7744b851/

Host and Organization:
Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/
Horton International (USA): https://www.horton-usa.com/
Insurtech Leadership Podcast: https://www.linkedin.com/showcase/insurtech-leadership-show

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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.

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.

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.

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.

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.

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).

Introduction

Insurance carriers spend enormous resources building and updating software. But when something breaks in production, finding the root cause - whether it's a data error in an XML file, a mismatch between an application and an underwriting system, or a workflow that behaves differently than expected - can take weeks. Sashia Godet has spent her career building the tools that catch those problems before they reach the customer.

Godet is the VP of Product at EmTech Group, a software development company focused on QA testing for the insurance industry. EmTech's flagship product, QMT, uses model-based testing to automatically generate test cases from business workflows - a fundamentally different approach from the script-based testing most carriers rely on. In this conversation, Josh Hollander and Godet dig into how QMT was built from a live carrier engagement, what the hardest part of product development really is, and where AI fits into the future of QA in insurance.

Guest Bio

Sashia Godet is the VP of Product at EmTech Group, where she has been with the company since its inception. She spent a decade in capital markets building compliance and regulatory solutions before transitioning into the insurance technology space. At EmTech, she leads product development for QMT, the company's model-based QA testing platform for insurance carriers and insurtechs, and is responsible for driving the product roadmap, cross-functional delivery, and market expansion.

Key Topics

Model-based testing: a different approach to QA

Most QA solutions for insurance rely on test scripts that have to be manually rewritten every time a workflow changes. QMT takes a different approach: the user defines the business workflow as a visual model - agent logs in, opens an illustration, fills an e-application, moves through underwriting - and QMT automatically generates the test cases in the background. The user never writes a test script. They define the process, and the platform handles the rest.

Built from a live carrier engagement, not a whiteboard

EmTech did not start with market research surveys. The original version of QMT was built alongside a large carrier whose pain points were visible in real time. When the team took that solution to market and validated it with other carriers and insurtechs, they found the same problems everywhere. That live research advantage gave EmTech a product that was already calibrated to real operational needs rather than theoretical ones.

Faster time to market is the core value proposition

The primary benefit carriers report is speed. By eliminating the time spent building and maintaining test scripts, development teams can get test cases faster, execute them sooner, find issues earlier in the cycle, and ship to production without the bottleneck that manual QA creates. For insurtechs building products for multiple carrier clients - each requiring individual customization and testing - the volume reduction is even more significant.

The hardest part of product development is the how, not the what

Godet is candid about where product teams most often stumble: not in identifying requirements, but in the technical implementation. Architecture that doesn't support a new feature, compatibility issues that surface mid-development, or requirements that shift while the product is still being built - these are the failure points that extend timelines and force teams back to the drawing board. Her advice is to spend more time in the requirements and technical design phases before writing a line of code.

XML and PDF validation added from direct customer feedback

Two significant QMT enhancements came directly from market conversations rather than internal roadmap planning. XML validation - checking that data moving between an application and an underwriting system is accurate before it reaches underwriting - was added after carriers identified rising not-in-good-order rates driven by data errors. PDF validation was added to replace the manual process of visually comparing two PDFs side by side, a task that provided limited coverage and was prone to human error.

AI in QA: the augmentation model, not full automation

EmTech introduced AI into QMT and is building toward agentic AI capabilities. Godet's philosophy is human in the loop: AI handles the volume and automation, but humans retain validation checkpoints where they can approve or reject AI-generated outputs. In a highly regulated industry where carriers are risk-averse and still exploring how to incorporate AI into their existing infrastructure, the augmentation model has generated better adoption than pitching full automation.

The product manager's most valuable skill: thinking in what-ifs

Godet's core lesson from years of product releases is the discipline of thinking through failure scenarios before launch - not just how the product is supposed to work, but what happens when a user does something unexpected. Carriers are never guided through a product with someone watching over their shoulder. They will interact with it in ways the product team never anticipated, and a well-built product handles those scenarios gracefully rather than crashing.

Notable Quotes

"The user isn't actually creating test cases or creating test scripts. Their focus is on just defining their business process in our software, and then we take care of the test cases and the execution on the backend."

"The key principle I follow in product management is always keeping your ear to the ground, making sure that your product is a fit for what customers need today."

"Software is never complete, as I like to say. But there is a minimum viable product that is really your threshold for do we release this version or we don't."

"We want to help you use AI, but human in the loop. So you have points of validation that you can say, yes, I want to use this - or no, I don't."

"I always think about what if someone does something else - because we're never sitting at our customer's screen watching what they're doing. We give them guidance, but they can do it in a completely different order."

Resources

Guest:

• EmTech Group: (verify and add URL)
• Sashia Godet on LinkedIn: https://www.linkedin.com/in/sashia-godet-2107931a/

Host and Organization:

• Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/
• Horton International (USA): https://www.horton-usa.com/
• Insurtech Leadership Podcast: https://www.linkedin.com/showcase/insurtech-leadership-show

Subscribe and Review

If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Apple Podcasts, and Spotify.

Introduction

In 2016, InsureTech Connect launched in Las Vegas with fifteen hundred attendees and a startup showcase at its core. Ten years later, ITC Vegas draws nine thousand people from carriers, reinsurers, brokers, independent agents, investors, and solution providers across the global insurance ecosystem. Bill Harris has been there for all of it.

Harris is the co-founder and Chief Customer Officer of ITC Vegas, the world's largest gathering of insurance innovation. He joined Josh Hollander ahead of the tenth ITC Vegas to walk through what has changed, what is new this year, and where he sees the event and the broader insurtech ecosystem heading over the next decade. The conversation covers AI adoption reality versus hype, the surprising rise of the independent agent at ITC, the looming implications of quantum computing on cyber, and how to navigate four jam-packed days in Las Vegas without burning out before the Goo Goo Dolls close out the week.

Guest Bio

Bill Harris is the co-founder and Chief Customer Officer of InsureTech Connect, the organization behind ITC Vegas, the world's largest annual gathering of insurance innovation. Since its founding in 2016, ITC Vegas has grown from fifteen hundred attendees to more than nine thousand, bringing together startups, incumbent carriers, reinsurers, brokers, independent agents, and investors under one roof each October at Mandalay Bay in Las Vegas. Harris leads the customer and attendee experience across the full event portfolio.

Key Topics

Ten years from startup showcase to industry homecoming

ITC Vegas was built from the start on a three-legged stool: innovators, incumbent carriers, and investors. The startup focus was always intentional, but the goal was always to bring the whole ecosystem together. What has changed over ten years is the scale — nine thousand attendees versus fifteen hundred — and the range of participants. Brokers, independent agents, LATAM delegations, and cyber professionals now have dedicated programming alongside the startup-focused content that launched the event.

The independent agent is ITC's fastest-growing cohort

A decade ago, the prevailing assumption was that technology would disintermediate the independent agent. That prediction has not played out. ITC Vegas now runs a full agents and brokers day on Tuesday with separate curated content stages for independent agents and brokers, a dedicated expo, and roughly five hundred independent agents expected to attend. Harris describes independent agents as ITC's fastest-growing attendee cohort, driven by growing recognition that trusted human advisors remain essential even as AI adoption accelerates.

Neighborhoods: finding your flock in a nine-thousand-person event

ITC Vegas carved its expo hall into neighborhoods several years ago, grouping exhibitors, stage content, and attendees by segment: LATAM, innovation and startups, life health and benefits, and distribution. The concept has been well received because it allows attendees to orient quickly and find their peer group without navigating a generic expo floor. Harris encourages first-timers to attend the Wednesday morning tour at 7:15am to learn the layout before the full event gets underway.

Gen AI is still king, but the real question is ROI

Two and a half years after ChatGPT launched, Harris observes that enterprise AI adoption is high but measurable results remain elusive at the organizational level. Individual employees are finding productivity gains on their own, but enterprise-wide initiatives have struggled to translate testing into real output. The conversations happening over lunch and drinks at ITC this year are not about whether to adopt AI — they are about what is actually working and how to get ROI out of it. Agentic AI for back office and workflow automation is the emerging next chapter.

Cyber is surging, and quantum computing is coming

ITC Vegas is adding a full-day cyber summit on Thursday for the first time, organized with advisory board member Amit Arora, a cyber expert and Columbia professor. Cyber is top of mind across the industry following high-profile incidents including carrier hacks and the Jaguar Land Rover disruption. Harris flags quantum computing as the issue people are not yet talking about publicly but should be: the convergence of AGI-level AI and quantum computing in the next four to five years will have massive implications for cybersecurity and the insurance products that cover it.

The next wave of insurtech founders looks different

Seed-stage insurtech founding activity has slowed. The technologists who thought they could figure out insurance from the outside are largely gone. What Harris is seeing now are second-time founders who came up through insurtech, acquired baseline industry knowledge, and are now going independent again — this time with the domain expertise that the first wave lacked. He expects the next round of innovation to focus heavily on brokers and on the life, health, and annuity space catching up to the innovation pace already set on the P&C side.

How to survive and get the most out of ITC Vegas

Harris recommends planning by the hour but leaving room for serendipity. Some of the most valuable connections at ITC happen waiting in line for coffee or sitting down at a lunch table with a stranger. Practical advice: attend the first-timers webinar before the event, take the Wednesday morning expo tour, wear comfortable shoes, use the ITC app to pre-book meetings, and download the ITC Vegas Week calendar of satellite events. The week ends with a Goo Goo Dolls concert in a venue small enough to put attendees twenty feet from the stage.

Notable Quotes

"I run the world's largest gathering of insurance innovation. That's what ITC has become over the last ten years."

"A lot of folks thought ten years ago that the independent agent was going to be disintermediated. I think very much so, even with talks about AI, that's less and less the case. People want that trusted human advisor."

"Everyone's testing and trying, but no one's really come out with, okay, this is actually how we're really using it, how we're really gaining benefits. A few folks have been successful, but generally speaking, it's still in that testing phase."

"Plan your time, but also allow time for serendipity. Don't over-plan yourself because you may just meet someone waiting in line for coffee."

"Insurance is about the people, the places, and the things that we love and protecting those things. Everyone has risk. It's just about how do we manage that risk day to day."

Resources

Guest:

• ITC Vegas: https://vegas.insuretechconnect.com
• Bill Harris on LinkedIn: https://www.linkedin.com/in/billharris3ubiq/

Host and Organization:

• Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/
• Horton International (USA): https://www.horton-usa.com/
• Insurtech Leadership Podcast: https://www.linkedin.com/showcase/insurtech-leadership-show

Subscribe and Review

If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Apple Podcasts, and Spotify.

Introduction

Every insurance transaction ends in a document. An application, an accord form, a policy binder, a renewal packet. The data collection happens digitally now, but the moment it has to go into a PDF or get routed for signature, most brokers and MGAs fall back to manual entry, email attachments, and copy-paste. Mang-Git Ng built Anvil to be the infrastructure layer that sits between the data and the document.

Anvil is a paperwork automation platform that serves insurtechs, tech-forward brokerages, and MGAs with a PDF filling API, embeddable e-signatures, and no-code workflow tools that turn complex multi-document processes into a guided digital experience. The company started industry-agnostic and found insurance by accident - when insurtech companies started signing up in volume and one neighbor at a WeWork desk turned out to be a Vouch Insurance founder. In this conversation, Josh Hollander and Ng dig into where Anvil fits in the insurance stack, why specialty lines are the sweet spot, and what the founder path looks like when you grow up in Michigan and end up building a document infrastructure company in the Bay Area.

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Guest Bio

Mang-Git Ng is the founder and CEO of Anvil, a paperwork automation platform serving insurtechs, brokers, MGAs, and organizations across fintech, HR, real estate, and government. Before founding Anvil, he worked at Flexport and Dropbox, both of which gave him early exposure to document-heavy workflows at scale. He began his career at Cisco before cold-emailing his way into an early-stage startup founded by the creator of Google Voice, which set him on the path toward founding his own company. Anvil's e-signature product is free with no limits on documents or signers, and the company monetizes on deep integration and workflow automation.

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Key Topics

Anvil is the inverse of most document tools

Most document automation tools focus on data extraction - reading what is already on a page. Anvil works the other direction: it takes data you already have and puts it into the document. A PDF filling API lets insurtech engineering teams make a single request and receive a fully populated document back. The templating process uses computer vision and LLMs to find empty fields, label them, and map them to a client's existing data schema automatically.

TurboTax for any set of insurance documents

Anvil's workflow product lets brokers and MGAs upload an entire package of forms, tag them once, and present clients with a single guided web form that dynamically routes responses, applies conditional logic, populates all the underlying documents, and routes them for e-signature. The output is a completed, submittable document package - without requiring clients to touch a PDF.

The ACORD wake-up call

Anvil launched without any insurance focus. When insurtech companies started signing up organically, Ng's team quickly learned that insurance paperwork is in a different category of complexity. The ACORD 101 overflow form - which functions as a catch-all for half a dozen other forms and has repeating page logic baked in - was the moment the team realized insurance forms would require serious investment to handle properly. They solved it, and ACORDs are now routine. Specialty lines, where there are standardized forms but no standardized process, remain the core target.

Brokers and MGAs over carriers

Carriers, Ng notes, are not incentivized to modernize their document processes. They make money on investment income from float, not on policy issuance efficiency. The parties with real motivation to speed up and clean up the paperwork layer are brokers and MGAs - especially tech-forward ones who already have software teams and data infrastructure but need the document layer to stop being a bottleneck.

E-signatures are free. Integration is the business.

Anvil made unlimited e-signatures free to use - no cap on documents, no cap on signers. The revenue model kicks in when a company decides to deeply integrate Anvil into their product or operations. Ng frames it directly: Anvil is to paperwork what Stripe is to payments. The infrastructure handles the complexity so engineering teams can focus on their core product.

Founder lessons: block the noise, hire for chaos tolerance

Ng's most consistent advice for founders is to focus inward rather than getting distracted by competitor announcements or fundraising headlines. On hiring, he describes actively talking candidates out of the job at the offer stage - describing the uncertainty, the workload, and the pressure - and treating continued enthusiasm after that conversation as the real hiring signal. On leadership, he is candid about being stubborn and working to create space for pushback rather than winning every argument in the room.

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Notable Quotes

"We are in the paperwork preparation, signature completion space. We get compared to DocuSign, but we really do so much more."

"We use AI and computer vision to automatically extract fields that need to be filled out and tag and label them so they can be used in your computer program."

"We're the service to process paperwork. Stripe is the service to process payments."

"Every company that starts as a platform dies as a platform. The customer doesn't want a platform. They want you to solve a problem or a process for them."

"When I hire somebody, at the closing stage, what I'm trying to do is talk them out of taking the job. If they're still excited by the chaos, they're probably the right fit."

"Startups are not a democracy. If we were a democracy, we'd move way too slowly."

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Resources

Guest:
Anvil: https://www.useanvil.com
Mang-Git Ng: https://www.linkedin.com/in/manggit/

Host and Organization:
Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/
Horton International (USA): https://www.horton-usa.com/
Insurtech Leadership Podcast: https://www.linkedin.com/showcase/insurtech-leadership-show

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Subscribe and Review

If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Apple Podcasts, and Spotify.