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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