The Leadership in Insurance Podcast - Insurtech & Innovation

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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