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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
February 19, 2022
AI and ML, Claims, Founder, InsurTech, Startup

Raj Pofale, Founder&CEO of Claim Genius

Gilad Shai
February 19, 2022
AI and ML, Claims, Founder, InsurTech, Startup
Raj Pofale, Founder&CEO of Claim Genius

Raj Pofale, Founder&CEO of Claim Genius, joins Gilad Shai to talk about Damage Estimation, Computer Vision, Going Global, and Bollywood.

Tagged: Raj Pofale, claims, AI, adjusters, damage estimation, computer vision, startup

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Gilad Shai
January 22, 2022
Venture Capital

Vivek Krishnamurthy, Principal Commerce Ventures

Gilad Shai
January 22, 2022
Venture Capital
Vivek Krishnamurthy, Principal Commerce Ventures

Vivek Krishnamurthy, principal at Commerce Ventures talks about startup performance, the future of insurance, Commerce Ventures, documentaries, and #crypto.

Tagged: Vivek Krishnamurthy, Commerce Ventures, Venture Capital

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Gilad Shai
January 15, 2022
Core System, CoreTech, Founder, InsurTech

Dan Woods, CEO and Founder, Socotra

Gilad Shai
January 15, 2022
Core System, CoreTech, Founder, InsurTech
Dan Woods, CEO and Founder, Socotra

Dan shares his background as a classical piano player and talks about the motivation behind Socotra, the value that a modern Insurance Core System provides to insurance companies, and to new digital MGAs, data, data and more data, and Metallica.

Tagged: core system, founder, Dan Woods, Socotra

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Gilad Shai
January 2, 2022
Ecosystem, Innovation, InsurTech, Thought Leadership

Happy New Year 2022

Gilad Shai
January 2, 2022
Ecosystem, Innovation, InsurTech, Thought Leadership
Happy New Year 2022

Jay Weintraub and Gilad Shai talked about the 3Cs of connections - Capacity, Capital, and Customers, random topics, and future conferences.

Tagged: Jay Weintraub, IT, con

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Gilad Shai
December 15, 2021
Commercial Insurance, Founder, InsurTech, MGU, Startup

Ian White, Co-Founder and CEO, Koffie Labs

Gilad Shai
December 15, 2021
Commercial Insurance, Founder, InsurTech, MGU, Startup
Ian White, Co-Founder and CEO, Koffie Labs

Ian White, co-founder and CEO of Koffie Labs, talks about insuring a commercial fleet of trucks, underwriting data, cartography, 200 data points, climbing Mtn. Kilimanjaro, and the "K" in Koffie.

Tagged: Ian White, Koffie Labs, fleet, trucks

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