InsurTech 2025: A Year in Review & Predictions for 2026

James BenhamTerra, this week's episode sponsor is revolutionizing the world of workers' compensation claims and policy management. Terra's cutting edge platform empowers insurers with comprehensive benchmarking tools, robust management systems, and an integrated ancillary services marketplace. Discover how Terra is driving innovation and efficiency in workers' comp at terra.insure. That's t e r r a dot I n s u r e. Today, we are reflecting on an incredible year for Insurtech. 2025 was packed with innovation, new ideas, AI, transformative tech that's shaping the future of insurance. Today, we're gonna dive into the biggest breakthroughs, the challenges we saw, what lies ahead, and really just the exciting tech and and processes and things people are doing as we step into 2026.

Again,

Rob Galbraithso excited to have with me and my cohost Rob Galbraith. Rob, how's it going? It's going well, James. Yeah. It's excited to be here for another year and recap. It it has been kind of a remarkable year for InsurTech. We're maturing. You know? I don't know that it's like full adult stage, but we got maybe some some healthy teenage puberty going on in the InsurTech space. So, yeah, I can't wait to dive into everything we've learned this year with you. Alright. Let's get to it. I'd say that 2025 felt like a real turning point for the industry.

James BenhamFor us, and you you know, I I run an almost 300 employee firm that builds technology for carriers, MGAs, TPAs, brokers. So we've got our hands in, you know, a whole bunch of different segments of the of the insurance business on policy claims, admin, distribution, you know, kind of up and down the value chain. This really felt like a very different year. AI definitely moved way beyond pilots, and insurers really started thinking more seriously and then implementing, artificial intelligence into their operations. Rob, you know, when you look back at the year, what development or shift stood out to you the most for carriers and SureTechs, MGAs, all these guys?

Rob GalbraithSo I'll give you two, James, and and definitely, you know, would love your your thoughts on this as well. So the first, right, AI, and it's kinda funny because it's like you could probably tune back to any of our year end reviews and we would have said AI like each and every year, but I totally agree with you that like this year and you know, honestly, I've been telling some folks that like the term AI is like, you know, you're talking about like, you know, kind of rules old school rules based AI or talking about like, you know, machine learning AI or you're talking about like large language models, Gen AI, like agentic AI.

What type of flavor are you talking about? And it's almost like you use the term software, right? Like in the past, like software probably was a sexy word when you talk about like how revolutionary software was for the business. And over time, it's just like, yeah, I need software to run everything and I have a bunch of like software and that could be like a, Windows installed program, that could be an app on my phone or whatever, but we don't even really use that term. It's just kind of baked in.

So I think we'll get to that point. We're definitely not there yet with AI, but I think to me the clarity is AI front and center, right, of each offering, of each enterprise. And I'm seeing more and more use this kind of term like AI native, right, or really leveraging the full capabilities of AI, not just like, oh, we can build you a little analysis RPA or whatever. So I think that, right, getting to the crux of like, you know, the harnessing the full power of our recent developments and obviously there's been, you know, huge leaps forward in AI over the last twenty four to thirty six months.

I think now you're actually seeing that in offerings, right, coming to. And I'd pair that with, I think we're now seeing more and more offerings that are, what I would describe, you know, the heart of insurance enterprises. And so that's going to be in your underwriting, that's going to be in your claims. It's not just opening up a new distribution channel. It's not just being able to offer products online or offer more niche products. And we saw obviously a buildup of a lot of MGAs and competing in spaces that maybe weren't attractive to some of the large players, right, in the industry where you weren't trying to compete with them head on.

Obviously, lots of discussions about lemonade over the years, right, is one of the few examples probably of like trying to go against some of big power ones. But now I think you are starting to see, I'm seeing more particularly in the claims space. So obviously James, you've been there for a while, but I think that was an area in the past like people were really afraid to touch, right? Just because of the regulatory nature, obviously depending on the line of business, right? You have a potential for litigation or whatnot.

So while it's core to every insurance company, I just think there was a hesitation to really get to that kind of part of your enterprise, Same with Resurrection and Pricing. But now, it's like you have to make that move, right? You cannot continue to work on old legacy systems. And obviously, you think people are getting fed up with some of those digital transformation efforts in the 2020s. And I won't name any companies out there, but I hear a lot of frustration out there with kind of what I would describe as the standard offerings that have been out there for a while.

So how about you? What have you seen? Again, you're more at the heart of this as somebody that's built the tech, that's talking to folks, that's selling tech, and and you've got competitors, right? And and people are gonna replace what they have or or have you augment. So, yeah, what are you seeing and hearing out there? I'll say this. This is my twenty fourth year in business. It's my twenty first year in insurance tech.

James BenhamSo it's been it's been a couple of decades. And I and and look. Back in the day, which was like a Wednesday, we we, you know, we were just trying to get off paper. Right? Like, that was the goal. It's like, let's just stop using paper. Let's stop printing things out. We're still trying to get people to stop printing things out, might I add. I I was at a client site a month ago trying to get them to stop using their printers. I mean, so we still have that going on.

Then we were trying to get them off of Excel. That is still well, well entrenched across the insurance industry. And then then we were trying to get off of on prem services in an into the cloud. And now look, I'm seeing major movement, let's say, versus five years ago when some of the larger insurance companies still were holding out saying we don't trust the cloud. Now they're in full tilt cloud deployment. And and why that excites me so much and, of course, this is across my customer base, across my prospect base.

You know, at JBK, we do professional services for carriers, TPAs, brokers, MGAs, where we build bespoke solution custom. We work on all of our systems. And, you know, I have a separate company, Terra, that, you know, is a core system for, like, smaller SIG, SIFs, and TPAs, primarily in work comp, but now we support commercial GL, commercial property, commercial auto for those small SIG, SIFs, TPAs that really need that. And small carriers, I mean, it's a it's a really unique market. And what I'd say is that what I saw happening in the market is what the, you know, customer preferences now are truly shifting toward even in the smaller tier, which has historically has been laggards on adopting technology.

And I'm talking about single state carriers, single state TPAs, a SIF or a SIG, which is also single state. I mean, there's hundreds of those organizations around the country that ensure a material percentage of The US workforce on work comp, a material percentage of commercial property or general liability. So, you know, don't rule them out because they do matter. Right? They're now saying, hey. We we don't we don't wanna own servers anymore. We don't wanna do this in Excel anymore. And so there that is a major shift in the last couple of years, but in particular this year.

And now at the end of this year, they're coming to me saying, how do we use AI so we can stop doing all this manual processing? And so I saw projects finally go into into production, and that's major. Because a a year ago when we did our recap, we we were still talking about lab projects. Lab, lab, labs, labs, labs. Pilots, pilots, pilots, pilots, pilots. Now now it's full tilt implementation where we're doing med record summarization on millions of med records. We're doing claim level summaries.

We're doing policyholder level summaries. We're doing far more accurate predictive modeling to estimate the total incurred prediction of a claim. Far more accurate machine learning modeling, to to to help advise on pricing and on renewability of policies. Like, there's remember, like, human in the loop is still a thing. We still very very much with the licensed human professional to make the final decision, but we've been able to roll out across our client base through our services and our products a suite of service offerings that I never would have imagined.

And I'll be honest. This year for me was a major year where I finally stopped saying, and I mean, stopped saying because I used to have to tell clients we can't do that for some things. I hate saying it because I like saying yes to everything. I I'm a big believer in yes and. Right? Saying yes and here's here's the cost. Here's the schedule. But before, sometimes clients would ask like, can we easily analyze a video? Well, yes. Actually, now we can. Can we easily analyze photos for fraud or or for damage assessment?

Well, yeah. Actually, we can. Hey. Can we read all the claim narrative when you're doing your your your your recorded statements on a claim? And can we call out the keywords and then summarize it and then and then populate static field. Yeah. Yeah. We can do that now. And before, I was like, know, that's really hard to do. Now I'm saying, no. It's kind of all possible. And that's a major shift as for a technologist saying, no. It's really anything's possible now. And then that also a year ago, I'd say very few people were using AI to write code, and now everybody's using AI to write code.

But there's still engineers driving the AI. And so that's the other really interesting thing is, like, I, you know, you I I I think we have to look very closely at what the role of an engineer is in the future. And we're seeing that just like with the low code platforms that came out that were supposedly easy to configure, they weren't. That were supposedly going to eliminate coders, and they didn't. Because we we ended up just providing low code staffing, low code teams to our clients with the same engineers that were writing the custom code.

I'll tell you this. Big conclusion. I personally think most of low code is dead in the next few years because it's so much easier to use cursor, Claude code, and other tools to build custom solutions that you don't actually need a low code platform sitting in the middle because these are really expensive. Like, for a big carrier, a low code platform is gonna run a quarter million dollars a year just in licensing, and then you have to host it. And it's middleware. Right? It sits in between the compiler and the user.

And so I think that, you know, if I were a low code company, I'd be really nervous. Whereas, you know, you you still need talent driving the agents and engineering the solution and responding to users, but it's just a different role. So we're having to continue to evolve the roles up. And so that I'd say that's a, a really big change this year, huge sea change this year in how quickly we can deploy technology. Also, like, what kind of solutions people are looking for, customer preferences.

Now they're actually looking for cloud native. Like, and they know what that means. That a solution wasn't just lifted and shifted into the cloud, but it's like architected and built for that solution and AI native as well. Like, do I have to buy a bunch of AI add ons or am I gonna get, you know, text summarization and machine learning models as part of the solution, which is what they're certainly looking for. And so those are, you know, some bigger shifts. And, you know, I'm seeing the demand there in underwriting departments and claims handling departments and among distribution.

And like on on AI for brokers, like a buddy of mine owns and runs power broker, they are doing amazing things around AI tooling for brokers that's dramatically changing, reviewing submissions, generating submissions, you know, normalizing records, consuming text. I mean, these super time intensive tasks that historically there was no chance of having a a machine do it. Now machines can do it. And and now it's live in prod being used. And that all happened in the last twelve months. And so, like, that's what's so exciting about what's going on right now, I think, is that it's that that it's it's game time.

Like, we're actually on the field playing with the new tools. Everybody's still trying to figure out exactly what business looks like in an AI world, you know, because now we have Gemini, you know, Nana Banana three that looks like it might wipe out the film industry and wipe out the I mean, like, you don't even know like, I've been generating ad ads and videos with with Google Vids, which runs on Nano Banana three Pro. It's amazing. It's Hollywood studio quality video at at my fingertips inside my Chrome web browser.

So, like, there's some stuff going on that that I don't think any of us really fully understand. But it's now it's it's in our hands. Whereas before, we were watching cool concept videos and TED Talks. Now we're like, no. No. I'm gonna go generate a video with AI. Oh, I'm gonna go do an analysis of Hey. I'm gonna have a machine learning predictive model, and I'm gonna summarize all this text, and I'm gonna do it instantly. And it's gonna cost pennies or or fractions of a penny.

Rob GalbraithIt's funny you say that, James, because I I'm thinking like my mind is still on, you know, what I would describe as the blocking and tackling right of insurance like you're saying like looking at the policy language and comparing it right if your broker may be comparing across products, right? Or if your claims adjust or like looking at that, do we have coverage here, right? Or what do we have and what do we not have? Medical records, like you said, you know, like maybe a property inspection videos, fraud, things like that, right?

Or if you had an auto accident, right? Pictures of the claims and whatnot and trying to figure out deep fakes. So actually, it's like cool new tools, but like kind of the basics, like you're still it's just a faster, efficient way to do what you're already doing. But like to your point, I mean, there is this aspect of like being able to do stuff you were never able to do before couldn't even dream of doing right? Just you know, unlocking brand new capabilities that I think is a few leaders are thinking in that space, but I think most companies probably aren't and probably should have at least one eye one eye on that as they focus on like, Just, you know, let's streamline our current processes and operations.

James BenhamYeah. I'm still seeing people that aren't actually in prod in production with AI talking about it as if they are. And that I I I think that that that group is gonna get narrower and narrower and narrower. You know what I mean? Because, like, as I go live with projects and so I would like for that to be the case. You know, you see them on stage talking about AI and you're and you know that, like, they don't have anything in prod. And and that's I I think before, like, those of us who have been hearkening the coming of AI, you know, we're working on it in labs, and now a lot of us have have it actually in production.

And so I think that that's just a big it's a big it's a big shift. You know, but it's also a big shift that that it's almost a foregone conclusion that the cloud is now deemed safe and that or or let's just put it this way. It's deemed just as risky as your on prem tech. And that that's really but, like, on prem doesn't have a lot of benefits that cloud has. And the other challenge is that if you really wanna leverage a lot of the AI frameworks that are out there, you actually need to have your unstructured and structured data in the cloud so you don't have to transmit it and then have it run.

Like with the OpenAI APIs in Azure, if you already have your data in Blob Storage in Azure, then then they can they can hit those buckets and they can go in and go to Blob Storage or grab the files or grab the videos or grab the, you know, the text, the documents, and they can do things with them, which is, like, super challenging if you don't already if you're not already cloud native. And and I and so that's what I'm hoping, you know, going into next year is that that they you know, that we that we continue to refine that data definition of cloud native, AI native so that the buyers get more sophisticated with this and recognize that maybe they're just buying an old old old Chevy with new Cadillac badging.

You know I mean? And and so that's and they're not gonna really get what they need out of systems. You know, we saw we saw a lot of challenges this this year too, Rob. You know, data quality issues have really become a problem with AI adoption because especially when you're dealing with takeover data. You know, takeover data is often really messy, and that there's a lot of takeover data. You know, when you have like like, if you switch to a new fully bundled carrier and they take over the claims or you switch to a new TPA and they take over claims or, you know, you can end up with a lot of data rolling forward from one organization to the other and you have problems in that migration.

That all slows down AI adoption because your training for your models is not great. We're seeing a lot of pressure in reinsurance markets too. Now things appear to be loosening up. Like we're starting to see some normalization of prices and, yeah, there are some there are some things that might be normalizing now. We definitely have some big changing customer expectations on what they're that they're expecting for how to interact with their their insurance company. Like, I finally was able to get some of my most I love this word, recalcitrant friends and insurance to be on board with two a texting.

Just that. That was a huge that was a huge fight for a long time. I can tell you Twilio makes it so much cheaper to do this, and and, you know, that's that's that's really wonderful as well. So, you know, Rob, from your perspective, what which of these challenges proved hardest for companies to work through in 2025 and and where do you see signs that things are progressing?

Rob GalbraithSo definitely like the business challenges. I mean, mentioned reinsurance, right? And I know a lot of people have put a lot of rate kind of into the system and they're just now starting to kind of, you know, get right what they think is an appropriate rate. And there's been like some legislation fixes. Like I think about Florida in particular, where the the the insurance market's gotten a lot healthier with some of the reforms. At the same time, I can tell you like, I was just at a conference last month where they were just talking about the plaintiffs bar, right?

And like, they're taking private equity money like so they're benefiting facilities technological and they're just getting bigger and better. I mean, that's all I see kind of on TV now. I'm a big sports fan, so it feels like it's either a plaintiff's attorney or an insurance company, right? That's replaced the beer and the car ads almost entirely, it seems like. So definitely a lot from that. But I would say from a technology standpoint, you know, you mentioned data quality and I would say just to your point, like leveraging the unstructured data part where they have it, but how can we unlock it?

How can we use it? How can we get the full benefits that we're seeing, you know, pitched to us and certainly are there from AI native. Then the other part I would say is a lot of talk about AI ethics, right? Increased regulatory scrutiny, a lot of talk in the legislation. And then the one you mentioned human in the loop already, right? Like the decisioning, is the AI making the decision or not? And it's like, oh, it's making the recommendations. And so, yeah, you have these like interesting gradients where it's like, okay, this is just like, you know, more efficient, like broader, you know, automation all the way to like making a quote unquote recommendation, you know, and it might even recommend the next step, not just like recommend a quote unquote decision, but recommend like, I don't know, if you choose yes, then we're gonna do this.

If you choose no, I'm gonna do this. Would you like me to do that, etcetera? Yeah, just trying to figure out what is the role, right, going forward for all sorts of different job classifications at companies and that whole idea of like, you know, are you replacing all the workers now? But they need to work with AI, right? Or if they don't work with AI, they may be replaced by AI, things like that. So I think that's just like the new normal. How we come to grips with this?

Like, what are the, we're seeing the tech, we're starting to believe the tech, we're going beyond like you talked about, like actually moving into production. So as a former innovation leader, I had tons of those kind of what I call the misfit toys where we do some type of pilot. It's partially successful, but the business doesn't want to like take over start being the bill payer like to me that was the ultimate success get off the innovation budget like now it's part of your, you know, operation budget or you know, you you funded at a a project level for going that way, right, as part of the capital allocation.

But yet, for like, okay, you decided the business, you're not willing to take over, you're not moving forward, well, we're gonna unplug and then all the users are screaming, No, we have to have this. We can't go back to the way that we were doing it before. And so we ended up kind of in maintenance mode, which obviously is not what you should be doing on your innovation team, but we were kind of keeping a lot of things on life support for way longer than they needed to be because we were kind of you know, mushy middle in between.

But yeah, so I think a lot of concerns about both implications internally, right? Change management's a big part of this, the communication fears, right? And obviously, if you're not proactive with your communication to your employees, to your customers, etcetera, like, you are gonna stir up, right? People are gonna fill in the void with whatever they come up with. But at the same time, I think this concern about almost like another shoe to drop or transparency, right, is kind of the one big, why is the AI making this decision?

How is it doing what it's doing and getting away from a lot of this black box. Know, I guess that was ten years ago, we were kind of, you know, oh, hey, I don't have to worry about the details. Well, now, like, everyone wants to get into the nitty gritty. So I think still coming to grips with what our new AI reality means for all of us.

James BenhamYeah. I mean, black boxes aren't really welcomed by regulators, I'll say that. And that's why even summaries have really need to be approved by license adjusters so they can can actually review the summary and approve it. Suggestions have to be reviewed and approved. I mean, every everything we gotta keep humans reviewing this data so that you you can't just turn it wild on your on your information and let it go make decisions or or let it fully automate because there has to be a review process in place.

So I think that's really an important phrase. Also, this year, I learned that the hardest part of all these implementation projects, whether it's two way texting or record summarization or claim summarization or, you know, the the the reserve prediction, risk prediction. I've worked on all those projects in the last twelve months. The hardest part is getting people to actually use it still. Honestly, that is still by far the hardest part. And it's like the last 5% of the project, and it's like 60% of the effort is getting them to getting to use it, to not flush it when they experience the first problem, to actually look at the the items.

You have you still have to pass the obvious test too. Like, if you have reserve predictions, total incurred predictions, or you've got a risk recommendation, it has to be front and center on the screen where the user's doing that particular item. If you push it off screen to another screen, users still they will not click on it. They will not go there. And so if you have reserve recommendations or let's say you're in comp and you want an ODG reference model where you're showing the ODG data or or what whatever it is, like, it's gotta be right there on the screen where you're setting reserves.

Like, has to be, like, literally, like, 10 pixels above the screen. I mean, it's it's you've got to focus on user experience. You gotta look at, like, okay. Is this is this three button clicks? Okay. How do we get it to one? How do we get to zero? Like, that that has to be, like, a really singular obsession On on all of our product suite and a lot of our client projects, we implemented Clarity, Microsoft Clarity, and it shows you this really it's a really amazing overlay tool that shows you a heat map of how your system's used, But it also shows you where users rage click, meaning they click so frustrated, they rage click.

It also shows you where they dead click, meaning they click on things they think are links and they're not. So it shows you all the problems with the interface, and it also shows you any errors that occurred. What's what's been really interesting about this is we've been taking the Clarity data, connecting it to quality assurance people, and having them review it, and then update the interface. And we've dramatically improved the user experience for adjusters and underwriters using that. Rather than interviewing them, just re reviewing the the just Clarity records the session, and then if you can review the recording, you can it it also Clarity leverages ChatGPT and AI as well.

So it'll actually summarize it and tell you where the problems in the interface were, and then you can actually use Cursor to code the corrections. It's really amazing. But the the the end of the day of all this of all this iteration is the end of the day of all this all these iterations is like a radically better user experience. And that's been really, really, really positive. So let's let's move on to partnerships. You know, they were everywhere. In 2024 and 2025, a lot of partnerships being announced.

Partnerships between tech companies and insurance companies, partnerships between insurance companies and tech first MGAs. The MGA market appears to have maybe cooled a little bit, whereas, like, it was interesting because you mentioned lemonade, and I went back and reviewed their stock price before the show, and they've had a massive rebound in their stock price where, you know, they've gotten down to, like, $5 a share. I mean, they were really down in the dumps for three years. And then all of a sudden, you see them tick up to $83 a share as of this morning, which is a major uptick.

You know? And you look at their their five year high, you know, they they they got up to, like, a $145. They're still about half of of their five year high, but still they're they're climbing. But they and and their their revenue is is 42% year over year. You know, they beat their EPS. They beat their revenue, but, like, I still don't think they're profitable. And so I just wonder, you know, are they being rewarded for revenue growth? Like, you know, are they are they being rewarded for maybe not making as big of a loss as they were supposed to?

I'm I'm trying to I'm trying to nail this down because because I feel like the IPO market's pretty cool on this. And, you know, you you there were some there were some prominent, new carrier IPOs in Florida that that were okay. Right? Not not not setting the world on fire, but okay. So it feels like the market has cooled a little bit to this. And so I'm still trying to dial in, like, what the implications are. So, like, yeah, if you're, like, lemonade still has a negative earnings per share of negative $2.37.

I mean, still losing money. And so I just wonder, like, how long are investors gonna give some of this before they make money? Because, like, the, you know, the the the core definition of InsurTech is an actual insurance company that that is tech first in every every way. Yeah. You know, and it's leveraging modern technology in a in a different process. But you look at the legacy carriers, they've all implemented a lot of these these same processes and technology now. So I'm not sure if there's a clear definition between a legacy company that's just now spending billions of dollars on AI and automation and an Insurtech that still can't seem to make any money.

And so I'm just trying to figure out, and I'd love to hear your thoughts on that, Rob. Yeah. I know. It's it's a great question. And

Rob Galbraithyeah. A couple of things. I mean, number one, right, we were kind of in that zero rate interest rate environment for almost a full decade right after the great financial crisis of two thousand eight. And I think a lot of that fed, right, fintech, then Insurtech, right, kind of the growth, then COVID hits, right, then this focus on profitability, a lot of deleveraging. That was definitely a theme a year ago that we really emphasized. And now it definitely feels like we're kind of, I guess, coming to a more like normal economy in the way that I'm being think about it in the insurance market.

And yeah, some lines are doing better than others, but like I don't know that this is as remarkable as like the last fifteen years have been, which is kind of crazy to say that it's been that long. And I totally agree with you that I think you know, most of the legacy players have adopted, you know, not necessarily like okay, they're fully modern right in their tech stack, but they've adopted a lot of these tools. A lot of the low hanging fruit has been picked or is currently, you know, about to be put in the basket.

So, if you're thinking about, an upstart, right, you're thinking about a differentiator, it's like, where is that coming from? And I do think a lot of the MGAs either, you know, that was just a faster way to become kind of an insurance company, right? Without the capital restrictions that, you know, a lot of, if you started as kind of a full fledged carrier, would have. Or it was a way, and I saw a lot of tech firms, right, instead of like trying to license their technology and go through that difficult sales cycle, as you painfully know, James, it's like they just decided to kind of like have the tech on the one side and become their own MGA.

I think some have been successful, a lot have not been successful that way, but it was kind of like a way to bypass the sales cycle. And I think that there was a mindset of there's an underserved aspect, right? And like I wrote about in my book, right? It's at that time, was a $5,000,000,000,000 market. I'm sure it's even more than that. Right? So even if you get, you know, one hundredth of 1% of the marketplace, you're gonna have a fairly healthy business just because of the size of the the insurance market.

But yeah, I don't know that a lot of those niche players are starting now, right? Some have found success and some others and so I think it is more about kind of partnership as you mentioned at the beginning, right? And kind of coming together and where does it make sense to consolidate, to partner up, what offerings and again, kind of my comment at the beginning of the podcast, right? The teenager, we're in the teenage years of maturity, we're growing up, right? And so we're starting to see some consolidation in the marketplace, not fully there, but it's not the wild wild what stays that it was kind of ten years ago when it really all felt kind of fresh and new kind of 2015, right?

And I think we'll continue to see that in the marketplace. So I think, you know, the cream is rising to the top in in some respects, and the market will continue to do so.

James BenhamYeah. Absolutely. Let's let's cover just who we got to talk to this year. Let's finish with that. We had we had some really wonderful episode. We started after last year's year interview, which, by the way, was almost the exact same day. Was December 0, the nineteenth. This it's currently the eighteenth as we record this, so we almost nailed it to a day. But we we started with episode one fifty three at the January. And we went through, you know, set really set functionally, like, 17 episodes that we that we we had in this year.

And we had some would just say we had amazing guests in 2024. We had equally incredible guests in 2025. Five. We started out with Rohan Malhotra from Road Zen talking about the next generation of auto insurance. And then we moved to Ramona Tanabe from WCRI. That's the Work Comp Research Institute talking about how their research is shaping the future of work comp. I've developed a whole whole new massive appreciation for what WCRI does this year, by the way, and some of the engagements I'm working on.

Then we had doctor Dan Carlin come on and talk about telemedicine, technology, the future of care, and how you can, you know, loss prevention. Hey. We wanna prevent losses in the first place. We're gonna put clinics on-site. We're gonna do all kinds of really cool stuff. Then we had Matthew Monson. I super eye opening. I'm sure you remember this one because he was talking about the unethical practices threatening insurance claims and was just really eye opening, wasn't it Rob?

Rob GalbraithAbsolutely. Yeah. Like we talked about just the yeah, plaintiff's bar that there I mean as you yeah, the vectors before, you know, litigation right and and regulation

James Benhamfeels like they know no no bounds as you kind of open up this Pandora's box. Yeah, Rob. I was I was in some meetings this week and I heard some more horror story. I mean, mean horror stories about plaintiff's litigation and what it results in and even plaintiffs getting it's just the stories are so wild, it's almost hard to believe them. And there are some states that have some really challenging laws that that have led to the need for a lot of technology around employment so that we can, you know, prove things, really interesting.

Then we had Bobby Collies on from Cotery talking about the Entrepreneur's Playbook, because she's really was busy disrupting the insurance company from within at Cotery. We moved on Prita Sakharan from Unum. She was identifying the right pain points and keys to AI success. Moved on to Jason Gross, talk from TruStage, talking about rethinking enrollment strategy and insurance. And then a very good friend of mine, Chris Griffith, came on. He's the president, at American Coastal. He went from literally being a help desk worker, rose through the ranks in technology, became CIO, and then chief information officer, not chief insurance officer, and then became president over there.

And he he did a lot of work at American Coastal and Skyway. They've had some new product launches and releases, and they have a very tech centric organization there. After that, we moved on to my a good friend of mine, Broker Brett, Brett Fulmer, talking about how tech is powering the modern agent. I really enjoyed that conversation. I know you know, Brett as well. Yeah. Very well. I think we got him on the new dad high as well. He was going on no sleep, all all fumes.

I don't know how many energy drinks he was patting prior to it, but the energy level was high with Brett. Yeah. And I've got him on. I I I talk to Brett regularly, and he's still on the new dead high. He's he's still he's still has a little kid. So if you're listening, Brett, love you. Glad you're out there. We then had Denise Olsen from k two come and talk about how analytics is is rewriting underwriting. Really appreciated the conversation I had with her at a conference and brought her on the show to talk about that.

We then had Frank Schmidt from Genre, small, you know, small company. Genre. It's about the the the intuition behind Genreve AI. I I had my good friend from Ohio, Dean Fidel, come on from the Ohio Insurance Institute talking about connecting people policy and progress, but they're dealing with some huge challenges in, you know, commercial trucking insurance that they have to provide. And that, again, driven largely by how litigious that industry is and how much technology they need to leverage there. Then I have my friend Stan Smith come on from Gradient AI talking about, you know, predicting outcomes.

And then the last four were, I think, just for really great home runs with Matt Crum. He you know, he's the the, president, I believe, CEO. There you go. Over at Frank Winston Crum Insurance. Steve Kapple, the CIO of Safety National, talking about the CI lens on CIO lens on data and AI. And of course, Steve talked Steve and I spoke at two different conferences in the last year together. My friend David Bell from Montana over at Alps talking about, and we talk about lawyers. They they actually are the nation's largest lawyers malpractice insurance.

And so there's a there's a flip side to that, and that's the lawyers need a lot of malpractice insurance. Then we closed up with that episode 169, my friend Andrew Bate from Valaris Re, who's really transporting transforming the hospitality industry, and that's through short term rental insurance. So I feel like we we got to have this amazing set of conversations with people from all over the insurance sector. We had a lot of executives at insurance companies on talking about their initiatives. And again, this is where I saw a big shift, Rob, in that we're not just talking to the head technologist, we're talking to the COO, the CEO, the president, and they're talking about their cloud initiatives, their data initiatives, their AI initiatives.

They're much more knowledgeable about that now, and and they can speak very intelligently about it. So I'm very pleased to see the leveling up of the of insurance executives.

Rob GalbraithYeah. I couldn't agree more. I mean, I I feel like we really had, some of the best quality that we've ever had right on the podcast. Not to say that we didn't have a quality podcast before, but, you know, highly curated, right? In terms of like who the guests were in a wide variety of roles, probably the biggest variety that we've had since we've been doing this. And yeah, you're right. I think a lot of the leaders, mean, A, it's great to just hear about their career.

Like, we've had some folks twenty, thirty, you know, up to forty years, right, in the industry. So it's always great to kind of hear, like, the journey and then what they've seen from a technology transformation standpoint. But to your point, like, you know, almost all of them could speak like impactfully about what they're seeing and being I think what struck me is that they're being very thoughtful and proactive in what they're looking to adopt. I think it's so easy and I see this all the time.

Company is just reactive to whatever the latest Gartner report is, Whatever the buzz is, right? Think about like blockchain and stuff like that. That's really come out right in the past and I remember like, you know, being ahead like, you know, I'm responsible now for all these mobile apps. Why do we have these mobile apps? Well, I don't know, but somebody said in 2016, we all, you know, everyone's going mobile. So we just put out a couple of mobile apps real quickly out there. They have no functionality, you know, nobody uses them, right?

But we're spending resource to maintain and nobody asks like, does this actually make sense? Is this something our customers want, right? So, I think, you know, for folks, if you have any downtime during the holidays, I know it's a busy time of season, but go back, check it out. Maybe there's an episode that you missed or you wanna listen back to, again, and, there's just a a lot of great information. You can check out the website, to find some of the past ones or or go back through your feed for sure.

I'll

James Benhamdefinitely say the other thing in general, I watch a lot of AI news now. There's some great channels I follow on YouTube that do daily coverage of AI news because it's moving so fast. If you're not working with Gemini three, please, please, please go work with it. Huge context window, incredible LLM. Nano Banana three Pro is amazing in images and video. There are just some crazy stuff with Veo. And Google Google, oh my gosh. They got caught flat footed by ChatGPT, but they came out of the corner of that boxing ring, and they punched a lot of people directly on the nose with Gemini three.

Go check it out. I would also encourage you to spend a lot of time inside of Azure and the Azure OpenAI API. Look at what Microsoft is offering. There's just some incredible stuff going on in the area of tooling right now. And, you know, the the wonderful thing about an open arms race is that ultimately, I believe the consumer wins. I I do because you're seeing Claude have to level up their game. ChatGPT leveling up theirs. Gemini three leveling up theirs. Of course, meta is don't leave them out there in the game as well.

So there's a there's a lot of players in this game, and they're they're getting they're getting their tech into into production. That that really is the wrap up of this year. I did want to just to just finish by giving a a really quick homage to one of my dearest friends who who passed away this year. We we had him on the the show 09/25/2024. It was his final episode. I interviewed with him. He did pass away in February. It was Skip Brechtel. Just wanna to, to give give him a shout out.

I don't wanna I don't wanna end the year without thinking about him. He was a transformative leader in technology and workers' comp. He was a very close friend of mine. He lost his battle to cancer in February. But his his impact lives on in a big, big way, and he he got me launched on some major projects right before he passed away and made it clear what his expectations were. And I just I just wanted to give a shout out to to his family and his his work family and his family family and all of his friends out there.

Because this was a, you know, for the first first year without him, But I just wanted to to respect and honor him. I also just wanted to to say thank you to all the friends that we have out there in InsurTech land that are so kind when Rob and I go to conferences and trade shows and conventions and local events at stopping us saying hi, hanging out. There are just some absolutely amazing people in the insurance business and the InsurTech space. The long timers especially that that recognize this is a marathon and not a sprint.

I know that I'll speak for Rob and myself to say thank you to everybody for for all the great hangouts that we had for me at REMS and and WCI and National Comp and Insurtech New York and and and and there's there's a lot of it was a lot of conferences this year. We got a lot coming up next year that I'm excited to attend. And I would encourage you if you're in listener land and you haven't been to a a really fun insurance technology event like Insurtech New York, Insurtech Hartford, insurance innovation sorry.

Sorry. Insurance Innovators Conference or, I mean, mean, it's it is Insurtech Insights, ITC Vegas. I mean, we can keep going. Right? There's a lot of those. Please, please go check one out and have some fun and geek out. With that, I'll I'll turn it over to you, Rob, for any final comments.

Rob GalbraithNo. I just think it's a fantastic year. I'm curious, James. So again, I think of you being more in the trenches on the front lines with the technology. I hear about it. I see it. Right? I experience it a little bit, but not nearly as viscerally as you do. So I'm curious. Any outlook for what 2026

James Benhammay bring? Well, it's the year of agents. You know, we're we're building quite a few agents now that are able to do really omni model agents. So that that to me is the the big transition, and that is you you've got an omni model agent that can really reference all of the different subsets of artificial intelligence that have been developed to date inside one OmniModel agent. So you can have it go on the web and do all the things that an old RPA bot could do.

You know, log into a website, download a sheet, but then perform an analysis, do a summary, create a graphic, analyze photos, analyze videos, analyze free text, prepare a recommendation, predict a model outcome, and then summarize it into a report, upload it to a website. That's available now. Coming up soon. As soon because, like, omni model super agents are coming in 2026. So expect some you know, you saw ChatGPT and others roll out agent mode this year. You're gonna see far more capabilities out of those agent modes in the next twelve months.

I I just say what else is coming? Even more even more cloud native adoption, absolutely coming. What I'm trying to bring along in the industry is a radical shift in the way that we contract and buy and license software. And so I, you know, if I have anything to do with it, we're going to radically reshape the the way the same way that HubSpot changed things for CRM where you, you know, don't pay anything until you're live and you have a month to month commit and you have simple contract terms.

Certainly, that's something that I'm trying to reshape in the insurance business, and I see some others following suit on that. I think that we've got to have more customer friendly terms, conditions, licenses, and payment schedules. More of the onus for a successful product implementation has got to be on the vendor. And I'd say that I'm seeing the winds shift on that. And that excites me because I think that, you know, as a technology industry, we've we've got to make sure customers happy or happy when you go to a restaurant and you buy food and you don't like it, you can send it back and they get you new food.

And the tech industry has kind of been a poop sandwich sometimes where, you know, you gotta you gotta you just gotta eat it. And I don't think that's that's a really great way of doing business. And so I'd say I see, some really wonderful things coming, not just in tech, but also in in in terms and the way that that tech companies and insurance companies partner and work together. And so I'm excited about that. So I think 2026 year 2026 is a is a big year when we can we can really continue to move the needle and then, you know, continue to get, you know, full scale adoption of a lot of these technologies to really dramatically streamline and deal with the inevitable labor shortage that we're going to have from continuing to lose some of the most experienced people in the industry to retirement when, you know, we're not bringing enough in.

And so I think that's a really important thing that we've got to tackle together.

Rob GalbraithIt's funny you mentioned that, James, because I know we're at the end, but that is something that I definitely hear about from leaders as well. It's almost like this race of, you know, as this latest generation of artificial intelligence and all of its capabilities come in, it's like, I need to have my experienced underwriters, my experienced claims adjuster, you know, you name it. I need them to interact with that system and in some senses train it before they retire, right? I need to take all that tacit knowledge that is in their brain and codify it somehow.

It's not just this apprenticeship of like, oh, you're gonna sit with somebody and train them over the next five to ten years, right? Because that model is broke. It doesn't work anymore. We're not seeing it anymore. There's too much movement. Nobody stays in the same place. But if I can use them and capture that kind of especially a lot of the nuances and stuff that isn't written down and isn't in code somewhere or whatever, right? That's just a huge boost. It is kind of this interesting almost race, right?

Of like, we want to capture all these people's knowledge before they leave the industry forever.

James BenhamAbsolutely. Great. Great discussion, Rob. As always, we always wonder how we're gonna fill the time and then we always fill more than the time allowed. So it's good to good to see you, my friend. And that this wraps up our look back at 2025 and what's ahead for 2026. Rob, always great having you here. Thanks for the insights, the energy, another year of incredible conversations, and most importantly, your friendship.

Rob GalbraithYeah. Appreciate it, James. Always good to be your copilot.

James BenhamI love it. A real copilot. A a live copilot. Not the AI variety. Not the AI variety. Yeah. Exactly. And to everyone listening, thanks for being part of the journey with us. If you want more deep dives, interviews, and industry analysis, head over to ensuretechgeek.com for our latest episodes. Here's your strong year ahead. Stay curious, stay innovative,