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March 13, 2026
Agent Technology, Brokerage, Core System, AI and ML, Agentic AI
Gilad Shai
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.

Anupam Gupta, CPO at Applied Systems
March 13, 2026
Agentic AI, AI and ML, MGA, Startup
Gilad Shai
Juan García, Co-Founder at Tuio

Tuio serves a segment that traditional insurers struggle with: digitally native customers who expect self-service insurance, transparent pricing, and fast claims resolution. Instead of building another digital wrapper around legacy systems, Tuio designed a platform that uses AI agents to optimize the two biggest drivers of insurance profitability: marketing and claims.

Juan García, Co-Founder at Tuio
February 17, 2026
Consulting
Gilad Shai
Katey Walker, Chief of Staff at Xceedance

“It was the first FAIR Plan launched in over 20 years.”

When a state becomes the insurer of last resort, it cannot improvise.
A FAIR Plan must operate like a real insurance company: capitalized, issuing paper, fully serviced, and compliant from day one.

In this case, the state had no funds in place.

Within 120 days, the Xceedance team:
Secured the required funding
Stood up full insurance operations
Built the vendor ecosystem
Launched services end-to-end
They were writing business within four months.

An exceptional example of how public-sector insurance initiatives still require private-market execution discipline.

🎙 Episode 145 of hashtag#InsurtechTalk with Katey Walker

Founders, operators, and industry experts—real infrastructure, not theory.

Katey Walker, Chief of Staff at Xceedance
December 21, 2025
Gilad Shai
Robert Lewis, CEO of INTX Insurance Software

In this episode, we go on an unexpectedly fascinating journey — starting with coyotes and foxes, moving through African farming and UK wildlife, and ending in the heart of what this conversation is really about: insurance, reinsurance, and building modern core systems for carriers.

Robert Lewis, CEO of INTX Insurance Software
December 21, 2025
Gilad Shai
Stephanie Mier, Chief Insurance Officer at ...

Stephanie Mier, Chief Insurance Officer for ServiceUp, talks about modernizing Direct Repair Programs (DRP) and in the insurance and auto repair industry and ServiceUP

Stephanie Mier, Chief Insurance Officer at ServiceUp
Gilad Shai
September 22, 2021
Founder, InsurTech, Startup

Stuart Winchester, CEO & Founder at Marble

Gilad Shai
September 22, 2021
Founder, InsurTech, Startup
Stuart Winchester, CEO & Founder at Marble

Stuart Winchester, CEO & Founder at Marble, talks about using rewards in the insurance industry, rebate laws, Marble, mass transit, and MTA.

Tagged: Marble, Stuart Winchester, Rewards, Rebate Laws

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Gilad Shai
September 7, 2021
Thought Leadership, Insurance Carrier, Innovation

Angela Noble, VP of Innovation at EMC Insurance Group

Gilad Shai
September 7, 2021
Thought Leadership, Insurance Carrier, Innovation
Angela Noble, VP of Innovation at EMC Insurance Group

Angela Noble, VP of Innovation at EMC Insurance Group, and Gilad Shai talk about Angela's philosophy about innovation, fostering innovation at EMC Insurance, the role of her team, and culture.

Tagged: Angela Noble, innovation, EMC Insurance, workers comp

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Gilad Shai
September 7, 2021
Ecosystem, Founder, InsurTech, Startup

Daniel Demetri, Founder and CEO, Trellis

Gilad Shai
September 7, 2021
Ecosystem, Founder, InsurTech, Startup
Daniel Demetri, Founder and CEO, Trellis

In this episode, Gilad Shai and Daniel Demetri talk about Trellis, an InsurTech startup that acts as a marketplace and follows the analogy of Plaid in the FinTech industry.

Tagged: Daniel Demetri, aerobatics, marketplace

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Gilad Shai
September 7, 2021
AI and ML, Startup, InsurTech, Canada

Ron Glozman, CEO and Founder Chisel AI

Gilad Shai
September 7, 2021
AI and ML, Startup, InsurTech, Canada
Ron Glozman, CEO and Founder Chisel AI

Ron Glozman and Gilad Shai talk about Chisel AI, snowboarding, obtaining data from insurance companies, and setting up a podcast.

Tagged: AI, data, Ron Glozman

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Gilad Shai
September 7, 2021
AI and ML, Commercial Insurance, InsurTech, Los Angeles, Startup

Alan Ringvald, founder and CEO of Relativity6

Gilad Shai
September 7, 2021
AI and ML, Commercial Insurance, InsurTech, Los Angeles, Startup
Alan Ringvald, founder and CEO of Relativity6

Alan Ringvald and Gilad Shai talk about Relativity6 pivot to provide accurate business classification API.

Tagged: AI, classification, Alan Ringvald, Relativity6, NAICS, Commercial Insurance, API

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