This week, host Alex Bond sits down with James Thom, Chief Product Officer at Vertafore, the insurance technology company powering agencies, MGAs, and carriers across the US and Canada.

James brings a fascinating perspective: from consulting at McKinsey to leading product at scale, he's seen first-hand why making the leap from recommendation to real-world implementation changes everything.

In this episode, we get into:

💡 Why AI transformation requires more than piecemeal adoption — and why the companies going all-in are seeing 2x–3x productivity gains

🏗️ How Vertafore's new Velocity AI platform is embedding AI natively into the tools insurers already use every day

🔄 The "human plus" moment — giving every individual a team of AI agents to multiply their impact

⚖️ How regulation shapes product development in a highly governed industry — and why that's not a bad thing

🤝 Why the build vs. buy debate has come roaring back, and how smart operators are thinking about their "secret sauce"

James also opens up about what's kept him at Vertafore for eight years — and it speaks volumes about the community they've built.

Whether you're in insurtech, distribution, or just fascinated by how AI is reshaping industries from the inside out, this one is well worth your time.

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What does it take to make AI work in insurance, not just in a pilot, but in production?

In the latest episode of the Leadership in Insurance Podcast, host Alex Bonds sits down with Kyle, founder of Clearcover and the newly launched Dearborn Labs, for a candid conversation about the realities of AI adoption in the insurance industry.

Kyle brings a rare perspective: a decade of building one of insurance's most tech-forward carriers, and now a mission to bring those hard-won lessons to mid-market insurers everywhere. He shares how Clearcover achieved over 90% of claims intake through AI agents and 93% of policies found digitally - and why getting there was far harder than it looked.

In this episode, Kyle and Alex explore:

🔹 Why traditional AI pilots are "a bridge to nowhere" and what truly embedded implementation looks like instead

🔹 The "last mile problem" holding insurers back from real AI value

🔹 How mid-market carriers and MGAs are being underserved by legacy consulting models

🔹 What it takes to embed AI directly into production workflows, not just bolt it on

🔹 The mindset shift required to move from cost centre to P&L impact

With AI capabilities evolving at unprecedented speed, Kyle's message to the industry is unambiguous: "there's no more time to wait." The technology is ready. The hard part is making it fit the business - and that's exactly what Dearborn Labs was built to solve.

Whether you're a carrier, MGA, or insurance leader trying to cut through the AI noise, this episode is essential listening.

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In the latest episode of the Leadership in Insurance Podcast, host Alex Bond sits down with Kasey Roh, Head of US at Upstage AI, for a conversation that stretches from the lessons of large-scale manufacturing automation to the cutting edge of AI-powered document processing in insurance.

Kasey brings a rare perspective — shaped by hyper-growth stints at Meta and Tesla — to the world of enterprise AI.

She reflects on witnessing Tesla's journey to scale Model 3 production, where the hard-won lesson was clear: attempting to automate before truly understanding every step of the process is a costly mistake. Only by mapping workflows end-to-end with domain experts first did the operation find its footing — a principle she carries directly into how Upstage approaches AI adoption in insurance today.

In this episode, Kasey and Alex explore:

🔹 Why understanding end-to-end workflows is non-negotiable before any automation begins

🔹 How Upstage made the leap from the Korean enterprise market — where it now powers over 60–70% of claims processing — to cracking the US market

🔹 The critical difference between how Asian and North American enterprises buy technology

🔹 Why OCR and LLM technology is transforming underwriting and claims processing, handling the complex "tail end" of documents that traditional systems simply can't

🔹 Whether AI will truly disrupt existing carriers, or whether it's the new AI-native players who will reshape the industry first

Kasey also shares her candid take on AI adoption in insurance: the proof-of-concept phase is ending, and organisations that haven't figured out governance and human oversight are going to struggle in the scale-up.

Whether you're in underwriting, claims, or leading digital transformation at a carrier, this episode is packed with hard-won lessons from someone who has scaled technology at some of the world's most demanding and successful companies.

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What does the future of underwriting look like and how close are we to getting there?

In the latest episode of The Leadership in Insurance Podcast, host Alex Bond sits down with Alex Schmelkin, Founder & CEO of Sixfold, to explore how AI is fundamentally reshaping the underwriting landscape.

Alex Schmelkin shares how Sixfold has evolved from building a helpful assistant for underwriters into developing end-to-end underwriting agents, capable of producing quotes as polished as those from senior underwriters, straight from a broker submission.

The results speak for themselves. One customer cut quote turnaround time by half and increased bind rates by 18% - not by replacing their underwriters, but by freeing them up to do what humans do best: build better relationships and find better risks.

On what's driving Sixfold's success, Schmelkin is clear:

"You can't be all things to all people in this AI world. Develop your killer product and bring it to your customers."

Alex and Alex also dig into the wider market landscape: why so many insurers are stuck in pilot purgatory with multiple AI solutions, and what it actually takes to find best-in-class capabilities that scale globally.

A fascinating conversation for anyone navigating the intersection of AI and insurance

#InsurancePodcast #LeadershipInInsurance #AIUnderwriting #InsurTech #Sixfold #Insurance

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What does real AI transformation in insurance actually look like and how is it different from just speeding up the same old processes?

In the latest episode, host Alex Bond sits down with Mark Twigg (CEO) and Rob Agnew (Chief Strategy Officer) of Agentiv-X — an AI decision co-pilot built specifically for complex risk markets.

They cover a lot of ground:

🔹 Why Lloyd's Blueprint 2 fell short and what the market still needs to fix

🔹 The difference between optimising legacy processes and transforming them

🔹 How Agentiv-X captures the rationale behind expert decisions to create a genuine AI trust layer

🔹 Their three-step approach combining large language models, senior practitioner input, and a proprietary decision science algorithm developed with the University of Manchester

🔹 The ongoing conversation with the FCA about AI regulation and why explainability isn't just a compliance tick-box, it's a competitive advantage

🔹 What the next two years could look like for transparency and consistency in underwriting

If you work in broking, underwriting, or anywhere in the London market, this one is well worth your time.

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In the latest episode of the Leadership in Insurance podcast, host Alex Bond sits down with Michael Streit, President of Applied Systems Carrier Business, for a fascinating conversation about the future of commercial insurance and the technology driving it forward.

Michael shares how Applied, a company with over 40 years of institutional knowledge, is tackling one of the industry's most persistent challenges: friction in the commercial risk submission process.

He explores how the recent acquisition of Cytora is enabling carriers to digitise unstructured insurance data using AI and large language models, all without forcing standardisation or compromising each carrier's unique view of risk.

The conversation covers three distinct phases of digitisation maturity (from basic document processing, through workflow orchestration, to full connectivity between agencies and carriers), and what it actually takes for carriers to become front of mind for brokers writing commercial risk.

Michael also reflects on the cultural challenge of sustaining innovation within a large, established organisation, and why the independent agent channel remains central to the insurance ecosystem.

Whether you're a carrier, broker, or insurtech enthusiast, this episode is packed with practical insights on where agency-carrier connectivity is heading — and how quickly it's getting there.

🎧 Listen now | [Link in comments]

#LeadershipInInsurance #InsurTech #CommercialInsurance #AppliedSystems #AI #DigitalTransformation #Insurance

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What does it take to transform the insurance broker industry from the inside out?

In the latest episode, host Alex Bond sits down with Will Johnson, Co-Founder and CEO of Gyde, to explore how his company is reimagining what it means to be an insurance broker in the age of AI.

Will shares how Gyde is on a mission to empower brokers to become true, comprehensive guides for their clients - providing the technological infrastructure, automation tools, and operational support to help them go far beyond a single line of business.

The conversation covers:

🔹 Why brokers are the most underleveraged, but critical entry point into the US healthcare and insurance system

🔹 How Gyde's M&A strategy is built around finding partner-aligned agencies, not just financial deals

🔹 The role of automation in solving the labour-intensive renewal process during periods like AEP

🔹 What building a culture of empathy and intellectual rigour looks like at an early-stage insurtech

🔹 Gyde's roadmap: from completing their leadership team to accelerating their AI platform (GydeOS & Gia)

Will brings a rare insider perspective, including experience at Oscar, and beyond — and it shows in how Gyde is speaking the language of the brokers they're building for.

If you work in insurance, healthtech, or benefits distribution, this one is worth your time.

#LeadershipInInsurance #InsurTech #Insurance #HealthInsurance #Brokers #AI #Podcast #FutureOfInsurance

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In this week’s episode, host Alex Bond sits down with Andrew Doran, CEO of UnderwriteMe, to explore what it really takes to bring AI into one of the most regulated corners of financial services — life and health insurance.

Andrew shares how UnderwriteMe operates a dual business model: a distribution platform powering up to a quarter of the UK's advisor protection market, and a B2B automation platform for underwriting and claims — two sides that constantly inform each other.

The conversation covers:

🔹 Why AI adoption looks like a "quiet evolution" in mature markets like the UK and Australia but a "grand revolution" in emerging ones like India

🔹 The danger of waiting for perfection and why incremental progress beats standing still

🔹 What the future really holds for human underwriters in an AI-driven world (spoiler: the role evolves, it doesn't disappear)

🔹 How to bring risk and compliance teams along early rather than treating them as a blocker

Andrew's take on navigating innovation inside a regulated industry is both pragmatic and refreshing. A must-listen for anyone working at the intersection of insurance, technology, and change.

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The next episode of the Leadership in Insurance Podcast is here  - and it's one not to miss.

Host Alex Bond sits down with Abbie Day, reporter at Insurance Insider and one of the  industry's most informed voices on AI, to explore what AI really means for the future of insurance.

Abbie brings a uniquely informed perspective: her interest in AI dates back to her Masters dissertation on editorial responses to the technology back in 2018, and she has since authored a widely-read six-part AI series for Insurance Insider.

In this conversation, she and Alex go beyond the hype to have an honest discussion about where the industry actually is on its AI journey.

They cover a lot of ground, including:

🔹 How AI is reshaping claims, underwriting and broking  - and what that means for the people doing those jobs

 🔹 The tension between efficiency gains and the human relationships that insurance has always been built on

🔹 The question every insurer is wrestling with: build in-house or buy in?

🔹 The concept of "ethical debt"  -  and why getting AI implementation right from the start matters more than speed

 🔹 What future insurance leaders will actually need to succeed in an AI-augmented world

🔹 Why the industry is shifting from talking about AI to doing something about it  - and what the early results look like

Whether you're a leader navigating AI adoption, a professional thinking about what these changes mean for your career, or simply someone trying to make sense of where insurance is heading — this episode is for you.

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Insurance"

In the latest episode of the Leadership in Insurance podcast, host Alex Bond sits down with Sharon Rodriguez, Co-Founder and CEO of Nevado AI, for a fascinating conversation about the future of artificial intelligence in the insurance industry.

With 20 years of insurance experience under her belt, Sharon shares how Nevado AI is using an agentic workforce to help insurers cut through operational inefficiency and regulatory complexity — without the friction of traditional outsourcing models.

The conversation explores some of the most pressing questions facing insurance leaders today:

🔹 What does it actually mean to be AI-native — and how do you build that infrastructure?

🔹 How should organisations rethink roles, training, and incentive structures in an AI-driven world?

🔹 What kind of leadership does successful AI integration demand?

Sharon and Alex also discuss the cultural shift required for companies to treat AI not just as a tool, but as a genuine part of the workforce — and why empathy and creativity are now non-negotiable leadership traits.

Whether you're an insurance executive, an ops leader, or simply curious about where AI is taking the industry, this is a conversation worth your time.

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