
Jeff Kulikowski
Jeff Kulikowski is Executive Vice President and Head of Cyber and E&O at Westfield Specialty Insurance, where he leads the company's US cyber and professional liability underwriting platform.
7
APPEARANCES
3
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Sep 2, 2026
How Insurers Are Expanding Risk Management for AI
0:11
0:17
0:26
0:40
0:51
0:04
I was curious if you're seeing insurance kind of evolving to include more AI-specific risk management services or loss prevention resources as well.

Jeff KulikowskiGUEST
Yeah, we've been evaluating them for a while, and I think you're going to see more of them.

Jeff KulikowskiGUEST
You know, we've been offering cyber risk management services now, and certainly since Westfield's inception, but the industry has been doing it for, you know, 24, 25 years now.

Jeff KulikowskiGUEST
And we've seen a huge benefit to our, especially our middle market and SME insureds, in that they now have access to you know, a discounted tabletop exercise rate or a virtual CISO, whatever it may be.

Jeff KulikowskiGUEST
And so we've been thinking about taking that, or sorry, we've been pushing that approach now on AI and As you can imagine, there's lots of vendors in the space that are willing to do this now.

Jeff KulikowskiGUEST
We've seen a massive amount of growth, so we're still evaluating a lot of them.
How Insurers Are Expanding Risk Management for AI
0:11
0:17
0:26
0:40
0:51
0:04
I was curious if you're seeing insurance kind of evolving to include more AI-specific risk management services or loss prevention resources as well.

Jeff KulikowskiGUEST
Yeah, we've been evaluating them for a while, and I think you're going to see more of them.

Jeff KulikowskiGUEST
You know, we've been offering cyber risk management services now, and certainly since Westfield's inception, but the industry has been doing it for, you know, 24, 25 years now.

Jeff KulikowskiGUEST
And we've seen a huge benefit to our, especially our middle market and SME insureds, in that they now have access to you know, a discounted tabletop exercise rate or a virtual CISO, whatever it may be.

Jeff KulikowskiGUEST
And so we've been thinking about taking that, or sorry, we've been pushing that approach now on AI and As you can imagine, there's lots of vendors in the space that are willing to do this now.

Jeff KulikowskiGUEST
We've seen a massive amount of growth, so we're still evaluating a lot of them.
How Insurers Are Expanding Risk Management for AI
0:11
0:17
0:26
0:40
0:51
0:04
I was curious if you're seeing insurance kind of evolving to include more AI-specific risk management services or loss prevention resources as well.

Jeff KulikowskiGUEST
Yeah, we've been evaluating them for a while, and I think you're going to see more of them.

Jeff KulikowskiGUEST
You know, we've been offering cyber risk management services now, and certainly since Westfield's inception, but the industry has been doing it for, you know, 24, 25 years now.

Jeff KulikowskiGUEST
And we've seen a huge benefit to our, especially our middle market and SME insureds, in that they now have access to you know, a discounted tabletop exercise rate or a virtual CISO, whatever it may be.

Jeff KulikowskiGUEST
And so we've been thinking about taking that, or sorry, we've been pushing that approach now on AI and As you can imagine, there's lots of vendors in the space that are willing to do this now.

Jeff KulikowskiGUEST
We've seen a massive amount of growth, so we're still evaluating a lot of them.
EP. 117: When AI Agents Go Beyond the Guardrails
3:16
3:33
3:46
3:56
3:07
And I'm curious from an insurance perspective, what makes this type of event different from a traditional cyber attack?

Jeff KulikowskiGUEST
But what makes it so interesting and newsworthy is that it in one fell swoop was able to highlight to the broader market and whoever was reading this, that there are risks associated with an agentic AI model.

Jeff KulikowskiGUEST
And so there's a rush to implement AI, whether usually internally or externally, everybody's talking about how it can change their platform, their services, their products.

Jeff KulikowskiGUEST
And specific to an agentic AI model, This is a case where the AI agent was given a task and operated along the guardrails given to it.

Jeff KulikowskiGUEST
And so to me, and I think to broader, we certainly talk about this at Westfield a lot, is it really does highlight the level of specificity needed when using an AI agent versus say, an AI model gone rogue.
5 MINS LATER
9:29
So for insureds or companies that are using AI agents, what questions are you seeing underwriters asking that they might not have been asking, you know, like a year ago or how have things changed in that regard?
EP. 117: When AI Agents Go Beyond the Guardrails
3:16
3:32
3:38
3:07
And I'm curious from an insurance perspective, what makes this type of event different from a traditional cyberattack?

Jeff KulikowskiGUEST
But, uh, what, what makes it so interesting and newsworthy is that it, it, it in one fell swoop was able to highlight to the broader market and, and whoever was reading this, um, that, you know, there are risks associated with an agentic AI model.

Jeff KulikowskiGUEST
Uh, and so there's a rush to implement AI, whether using it internally or externally.

Jeff KulikowskiGUEST
Everybody's talking about how it can change their platform, their services, their products.
6 MINS LATER
9:29
So for insureds or companies that are using AI agents, what questions are you seeing underwriters asking that they might not have been asking, you know, like a year ago? Or how, how have things changed in that regard?
EP. 117: When AI Agents Go Beyond the Guardrails
3:16
3:33
3:46
3:56
3:07
And I'm curious from an insurance perspective, what makes this type of event different from a traditional cyber attack?

Jeff KulikowskiGUEST
But what makes it so interesting and newsworthy is that it in one fell swoop was able to highlight to the broader market and whoever was reading this, that there are risks associated with an agentic AI model.

Jeff KulikowskiGUEST
And so there's a rush to implement AI, whether usually internally or externally, everybody's talking about how it can change their platform, their services, their products.

Jeff KulikowskiGUEST
And specific to an agentic AI model, This is a case where the AI agent was given a task and operated along the guardrails given to it.

Jeff KulikowskiGUEST
And so to me, and I think to broader, we certainly talk about this at Westfield a lot, is it really does highlight the level of specificity needed when using an AI agent versus say, an AI model gone rogue.
5 MINS LATER
9:29
So for insureds or companies that are using AI agents, what questions are you seeing underwriters asking that they might not have been asking, you know, like a year ago or how have things changed in that regard?
AI Insurance Risks Could Become the Next Silent Cyber Crisis
0:25
0:54
1:04
1:16

Jeff KulikowskiGUEST
And AI, especially over the past couple of years, has really been at the forefront of insurance because people are just trying to understand what is the risk? You know, how do companies utilize it? What are the effects of it? You know, whether it's movies that give people fear around a Skynet scenario or You know, just general talk about it, you know, AI is understandable and we look at it from a different perspective where we try and understand the underlying models that our firms are, sorry, that our insureds utilize.

Jeff KulikowskiGUEST
We try and understand how they're utilizing AI, whether it's from an operational model or operational efficiency standpoint, whether it's customer facing, but it's underwritable.

Jeff KulikowskiGUEST
And you have seen exclusions in the marketplace around AI, but it's been our opinion at Westfield that for the most part, your AI risk as a professional service firm is going to be covered in broader parts of your E&O policy.

Jeff KulikowskiGUEST
And where you get into a bit of an issue is companies that don't have an E&O policy, then they may not have that same level of AI operational risk covered.

