Brokerage, MGA, MGU, AI and ML, Distribution, M&A
Gilad Shai
Curtis Barton, CEO of ALKEME

Curtis Barton started Alkeme in October 2020 with seven agencies, $25 million in combined revenue, and a simple argument: stop running a lifestyle business and start building generational wealth. Five years later Alkeme is at $350M+ in revenue, 35 states, 110+ locations, and 85+ acquisitions. In Episode 160, Curtis explains why most consolidators are more overleveraged than they admit, why organic growth is the only honest metric in the rollup game, and why every insurance brokerage — whether it wants to or not — is becoming a software company.

Curtis Barton, CEO of ALKEME
AI and ML, Claims Management, Claims, Agentic AI, Workers Comp, Startup, Founder
Gilad Shai
Heather Wilson, CEO of CLARA Analytics

A finger cut came in as a severity one workers comp claim. Nobody looked at it for 90 days. CLARA's models kept reading the incoming medical documentation — and caught the trajectory shift before any human did. By the time the alert fired, the case was heading toward amputation, not a bandage. In Episode 159, CLARA Analytics CEO Heather Wilson explains how claims AI actually works in practice: not as a replacement for adjusters, but as a 24/7 safety net that catches what tired eyes miss — and what she wants to accomplish before she leaves this industry: finally connecting the claims intelligence that closes cases to the actuarial intelligence that prices them.

Heather Wilson, CEO of CLARA Analytics
Parametric Insurance, MGA, Climate Risk, Reinsurance, Carrier, AI and ML
Gilad Shai
Sid Jha, CEO of Arbol

Sid Jha didn't come from insurance — he came from Citadel, trading commodities, pricing weather risk. In Episode 158, he explains how that background shaped Arbol's thesis: that parametric insurance wasn't just a claims shortcut, but a bridge to entirely new pools of capital that traditional insurance could never access. We also get into why Arbol stopped being a pure parametric company — and why being ideological about your product is the fastest way to miss what the customer actually needs.

Sid Jha, CEO of Arbol
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
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Jame Benham, CEO of JKB and Terra

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Jame Benham, CEO of JKB and Terra

James Benham has been building technology for insurance companies for 25 years — not InsurTech, actual technology. In Episode 150, he makes two arguments the industry needs to hear: first, that shadow AI is a compliance crisis hiding in plain sight at virtually every carrier, TPA, and MGA; and second, that roughly a third of the insurance workforce is performing manual clerical tasks that should be automated — while the industry simultaneously struggles to find enough qualified adjusters and underwriters. The fix to both problems runs through the same place: AI that is embedded, tested, and governed rather than bolted on or used ad hoc.

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Kitt Doucette, Co-Founder, WISH (Wildfire Insurance Solution Hub)

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Kitt Doucette, Co-Founder, WISH (Wildfire Insurance Solution Hub)

Kitt Doucette is a fourth-generation insurance professional, former adventure journalist, and the co-founder of WISH — the Wildfire Insurance Solution Hub. In Episode 149, he makes a case the industry needs to hear: wildfire conflagration is not the same peril as wildfire, and treating it as a line item inside a legacy package policy is why the California market is broken. The fix isn't just better models — it's using those models proactively, communicating risk at the parcel level, and giving homeowners a clear ROI for mitigation before the fire arrives.

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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.

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Juan García, Co-Founder at Tuio

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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.

Josh Dorfman, co-founder and CMO of Plantd

Josh Dorfman, co-founder and CMO of Plantd

Episode 146 | Climate Tech, Construction Innovation & Insurance Risk

What does climate tech have to do with construction and insurance?

In the first InsureTech Talk episode of 2026, I sit down with Josh Dorfman — climate entrepreneur and Founder of Planted — to unpack the intersection of climate innovation, supply chain resilience, advanced manufacturing, and insurability.