Core System

Kasey Roh, Head of USA, Upstage

Kasey Roh, Head of USA, Upstage

Upstage's Kasey Roh came to enterprise AI through Tesla, Meta, and venture capital — which means she has seen enough AI companies to know the difference between real technology and a wrapper. In Episode 152, she makes the case that insurance companies have only ever been able to read about 20% of their documents, explains why throwing the rest into frontier LLMs is not a scalable solution, and shares what one Asian carrier found when it finally digitized a decade of untouched claims records — enough to launch two entirely new product lines from data it already owned.

Anupam Gupta, CPO at Applied Systems

Anupam Gupta, CPO at Applied Systems

AI won’t replace insurance brokers.

But it will change how their work gets done.

In Episode 148, I spoke with Anupam Gupta, Chief Product Officer at Applied Systems, about how AI is transforming the brokerage tech stack.

One idea stood out:

Instead of replacing humans, AI will become digital teammates working behind the scenes.

For example:

• AI agents preparing renewal packets
• Extracting data from submissions and emails
• Comparing carrier responses
• Surfacing missing coverages

The result?

Less administrative work.
More time for brokers to do what actually matters: advise clients.

One of my favorite lines from the episode:

“Imagine every employee showing up like your top 10%.”

That’s the real promise of AI in insurance.