Reghan Brandt
Reghan Brandt is the Chief Digital Operations Officer at K2 Insurance Services, where she leads digital transformation across multiple insurance divisions. She is also the founder of LossRun Pro and President of Columbia Pacific Finance. With two decades of experience building and modernizing insurance operations, Reghan is a practitioner of the people-first philosophy: understand the business before you modernize it.
Why Insurance Modernization Fails (And How to Do It Right)
There's a story that defines Reghan Brandt's approach to insurance. She's at a wedding. She's had a few cocktails. An insurance agent mentions premium financing. She has no idea what that is, but she nods convincingly anyway. The next morning, hungover at 6 AM, she Googles "premium financing," learns what it actually means, and - by pure chutzpah - gets hired to lead the business.
That job became Columbia Pacific Finance.
This origin story isn't just cute trivia. It reveals something fundamental about Reghan's philosophy: domain expertise comes from immersion, not theory. Not everyone can pull off a bluff at a wedding and build a company from it. But everyone can understand the principle: you have to get your hands dirty. You have to understand the business before you try to modernize it.
This lesson shaped every subsequent venture. When Reghan started learning the insurance business in earnest, she didn't join a think tank or attend a conference. She drove from Seattle through Wyoming - literally stopping at independent agent offices, one by one, asking questions, listening, learning. At 24 years old. That's not a summer internship. That's a commitment to understanding.
Today, Reghan is Chief Digital Operations Officer at K2 Insurance Services, a multi-division insurance company facing the very real challenge of modernization at scale. And her perspective on why modernization projects fail - and how to make them work - cuts through the hype and gets to the actual barriers.
The Real Barrier: Change Management, Not Technology
Here's what most companies get wrong: they believe insurance modernization is a technology problem. Pick the right software. Implement it well. Done.
Reghan disagrees. "The tech you can build anything now. It's going to be change management."
This might sound simple, but it's profound. Consider what modernization actually requires in an insurance organization:
1. Articulating hidden workflows: Insurance professionals - underwriters, adjusters, agents - have decades of knowledge living in their heads. They make decisions based on intuition shaped by years of experience. When you ask them to explain exactly how they underwrite a risk or adjust a claim, they can't. Not because they're being evasive, but because so much of their process is implicit. "I just know it when I see it." Digitizing that is brutally hard. You can't code what you can't describe.
2. Building buy-in across the organization: When you implement new technology, you're asking people to change how they work. That's threatening. It challenges expertise built over decades. It introduces uncertainty. The person who was the fastest underwriter on the old system might be slow on the new one (at first). That's demoralizing. Building genuine buy-in requires addressing fears, training thoroughly, and - critically - showing that the new system makes their job better, not just more compliant.
3. Managing the edge cases: Software demos always look perfect. "Here's a standard case, flowing through the happy path, everything works great." Real insurance is nothing like the happy path. State regulations vary. Policies have quirks. Claims have complexities. Edge cases break every system. Managing those edge cases requires subject matter experts working alongside technology vendors - not handing off responsibility once the software is installed.
Why InsurTech 1.0 Failed: No Boots on the Ground
The early wave of InsurTech (roughly 2010-2016) was characterized by a particular approach: young tech entrepreneurs from Silicon Valley looked at insurance, saw inefficiency, and said "we can fix this with software." Many of these founders had never read an insurance policy. They didn't understand state regulation. They'd never sat with an agent or an underwriter. They just saw "market opportunity."
Their goal was often to disintermediate - to cut out agents, replace underwriters with algorithms, "disrupt" an industry they viewed as hopelessly outdated.
Reghan's take on this wave? "InsurTech 1.0 was cynical."
What failed wasn't the technology. It was the assumption that you could modernize an industry without understanding it. You can't replace agents without understanding why agents exist and what value they provide. You can't automate underwriting without understanding the judgment calls and the edge cases that make underwriting an art, not a formula. You can't build state-compliant systems without understanding state regulation.
The founders who succeeded weren't the ones with the fanciest technology. They were the ones who got their boots on the ground, learned the business, and built solutions that made the existing ecosystem more efficient rather than trying to blow it up.
Reghan exemplifies this approach: Columbia Pacific Finance (premium financing), LossRun Pro (loss run aggregation and distribution), and now K2 (operational transformation). Each venture started with a deep understanding of a specific pain point in the insurance value chain. Not a solution looking for a problem. A problem understood intimately, then solved with appropriate technology.
Data Transparency Builds Loyalty; Hoarding Builds Friction
Here's a question that reveals how insurance companies often think: How do we keep customers from leaving?
Some answer: "Make it difficult to leave. Hoard their data. Create lock-in. Make switching costs so high that they stay because leaving is painful."
Reghan's answer is different: "You don't want to only keep business because you made it so difficult to move."
This is a data-transparency insight. Carriers have access to loss run data, claims history, policy information. Agents need access to this information to do their jobs. But some carriers restrict access, reasoning that if their customers can't easily access their own data, they're locked in.
Reghan's pushback: that's backward. Restriction creates friction. Friction creates resentment. Resentment drives customers to look for alternatives. And when they do, they leave - because they were never truly loyal, just captive.
Transparency, by contrast, builds trust. Trust opens the door to longer-term relationships. "Once you get the trust of customers, the sky's the limit."
Know What You're Solving For Before You Buy Software
Here's a pattern Reghan has observed repeatedly: a company sees a competitor adopt new software, or a vendor gives a slick demo, and a decision gets made to buy. Budget gets allocated. Contracts get signed. Implementation begins.
But nobody actually defined what the company is trying to accomplish.
"Sometimes people who are buying software don't even know what they want the outcome to be."
This is a costly mistake. Because when implementation hits reality, when the edge cases emerge, when change resistance surfaces, there's no clear north star. No shared definition of success. Just confusion and frustration.
Reghan's approach flips this: define outcomes first. Then pick software that can deliver those outcomes.
This requires discipline: Getting stakeholders in a room. Asking hard questions. "What are we actually trying to accomplish? Faster underwriting? Better underwriting? Fewer rejections? Higher approval rates? Better customer experience? Lower costs? Happier employees?" These are different outcomes, and they may require different solutions.
The Framework: People, Process, Technology - In That Order
Reghan's approach to modernization is grounded in a simple framework: People, Process, Technology.
Most companies start with Technology. They pick software, implement it, and hope people and process adjust.
Reghan reverses this
1. People first: Who are the users? What do they know? What are they afraid of? What's the change management strategy? How will you build buy-in and capability? This comes before technology.
2. Process second: Given the people involved, what is the actual process we're trying to enable or transform? What are the key steps? Where are the decision points? Where are the edge cases? What training is required? This is where you articulate the implicit knowledge and define how work flows.
3. Technology third: Given the people and process, what technology enables this? Should you buy, build, or partner? What's the implementation plan? How do you support people as they learn new systems? This is where technology serves people and process, not the other way around.
This order is counterintuitive in a tech-forward world. But it's the order that actually works.
The Edge Case Problem: Why Software Breaks in the Real World
All insurance software developers encounter the same problem: demos work great. Real-world usage breaks.
Why? Insurance is full of edge cases. An employee moves to a different state mid-year. A family situation changes. A claim involves unusual circumstances. A policy has been amended three times. The standard workflow doesn't apply. The system breaks.
Reghan's solution: have one clear owner for each technology project. Not a committee. Not consensus. One person responsible for making decisions about how edge cases are handled, what happens when the system doesn't work, and how to escalate issues.
This owner doesn't have to know all the answers. But they have to be empowered to make decisions quickly, escalate appropriately, and own the outcome. Without this clarity, edge cases create confusion, support costs spiral, and user frustration grows.
Key Takeaways
About Reghan Brandt
Title: Chief Digital Operations Officer, K2 Insurance Services
Additional Roles: Founder of LossRun Pro, President of Columbia Pacific Finance
Background: Reghan's career in insurance spans two decades, starting with a wedding-night bluff about premium financing and evolving into operational leadership at scale. She has founded and led successful fintech ventures in insurance premium financing and loss run data management. Her current role at K2 involves overseeing digital transformation across multiple insurance divisions and business units.
Connect with Reghan Brandt
The full transcript
Transcribed automatically from the episode audio, so some names and terms may be misheard.
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 terra.insure. And we are back with another great episode of the InsurTech Geek podcast. With me, I am, of course, your host, the InsurTech Geek, James Benham out of College Station, Texas, home of Texas A and M, who had a great football season until the first round of the playoffs.
That's okay. We won't we won't think about that much right now. It's it's alright. With me, a a fellow lover of Texas and Michigan, my illustrious ghost, the most interesting man in insurance from San Antonio, Texas, mister Rob Galbraith. Rob, how are doing?
Rob GalbraithDoing well, James. Happy New Year. It is officially 2026, and I had to repeat it for the first time this morning, and I did not screw it up. So I was happy. Boo. I say boo to that. I I I wasn't ready for 2025 to be over. I'm like, nah.
James BenhamLet's stretch it out. 2025 was like a I blinked and it was done. It was it was one of those, like, the days are long and the years are short. The older I get, the more true that saying is. Especially when you have, you know, your kids start to grow up and leave the nest and all that stuff. It's a it's a weird weird phenomenon. But with us from a beautiful place, beautiful place, Missoula, Montana is Reghan Brandt. Regan, how are you doing?
Reghan BrandtI was doing better until I heard Rob's a Michigan fan that he they just creamed Gonzaga.
James BenhamThat was a painful day. Michigan Michigan State. Michigan State. Okay. I was like, woah. I gotta get off this call. No. No. He's fans of the state of Michigan. He he went to Michigan State.
Reghan BrandtOkay. Okay. Much love then. We're on the we're on the same page then. We're okay. So He hates the blue. Trust me. Don't you, Rob. I was like yeah.
Rob GalbraithRight, Rob? Yeah. No. And I will say as somebody that has a terrible football team that struggled with a previous coach getting into lots of off field trouble, I was not sad to see the same thing that happened to our fiercest rival.
James BenhamWell, there you go. See? Something about the state of Michigan and football coaches. We cannot keep them on the straight and narrow. It is. It is. It is what it is what it is. You know, we're definitely gonna steer clear of that one. So we're we're we're here to talk about insurance tech, not football or basketball. But I I I will say we're in the middle of the college football playoffs. I am loving having a real playoff. If it weren't for the Big Ten, we'd already be at a 16 team playoff.
I just don't wanna point that out that the only holdout on that on a 16 team playoff was the Big Ten commissioner. So if if he's listening, and I know that he loves insurance tech news. Dude, get over it. Just come on. I know it doesn't benefit you, but just just sixteen sixteen. Then we have all the it'd be it'd be great. Maybe 24. I'd love that too. 32. So we don't have go bigger than 32. I was actually reviewing the d one, two, and three FPS FCS playoff structure last night just to try and get my head around it.
And, you know, everybody else has it has it figured out. We're just slow to roll because all these bowls, if you didn't know this, all these bowls are are are independent five zero one c three nonprofits nonprofits, and their CEOs. And I looked at it. The average compensation is between 800,000 to a million dollars a year to be the CEO of one game a year. And, and so they're deeply entrenched. They like their paychecks. They don't wanna let go of the bowl game. Of course, the bowl games had to, like, let in five and seven teams because they couldn't like, a bunch of people opted out like Notre Dame, much little whiny babies, you know, opted out of even playing a bowl game because they're whiny babies, and they don't wanna join a real conference.
And so, you know, it is what it is. I love Notre Dame, but don't be a whiny baby. Just join a real conference. Play real football. Stop playing Georgia Tech. Let's play some real football. Let's get it on. Now I say that Miami, the ACC, which we love to make fun of in the SEC, whooped up on my Aggies and on Ohio State in a bad way. And it was like, oh my gosh. Their defense was amazing. So that's all I gotta say about that. I was watching Montana Tech play, Regan,
Reghan Brandtyesterday. Last night? Montana State. Yep. Yeah. Yeah. Yeah. State. Montana State. I'm sorry. Montana State. Yeah. It was the first time too that we played the grits. I'm a grits. So I was definitely not cheering for the cats last night. So when they missed, I don't know if you watched that game, but to end it with two missed kicks, like, insane. Insane. Like, I felt so bad for Illinois. I'm like, how does that happen? Two blocked kicks within thirty seconds. Like, I mean, never. Never in a championship game.
So but I'm happy for the state, although it is painful anything for the Cats when you're a Griz fan. So Yeah. I mean, you guys actually
James Benhamyou're pretty serious about that rivalry, and I appreciate that. Oh,
Reghan Brandtis Yeah. It is cutthroat. We had some friends. We were gonna possibly go to the game, and then we were like, it's probably not actually that good of an idea. And they went and they were like, yeah, we brought our kids. It was not good. It was ugly. Like, we we instantly regretted it. This this rivalry is is pretty intense.
James BenhamSo I love it. I love it. I love it, man. It doesn't matter of the size of the team, the size of the stadium's rivalries are Oh. They're they're they're they're rivalries no matter what. You know? Yeah. It's amazing. It's amazing. So let's talk about we're gonna talk about insurance. We're gonna we're gonna talk about k two. We're gonna talk about loss run pro. But I wanna I wanna talk about you for a minute and go back and and kinda talk about, like, where where were you born and raised, and what did you dream of being when you were a kid?
Reghan BrandtOh, wow. That's a loaded question. I grew up in Missoula, Montana, but at fifth grade. And honestly, to this day, it's funny we've been talking about sports. My dream job is a women's basketball coach. I'm like, when I retire, I'm like, I'm gonna either do high school or college basketball coaching, and I'm like, I think it would be the most fun, most rewarding job. I just loved playing basketball. I'm only five nine. I wasn't super skilled, but being from a small town, as my dad likes to point out, I was class b.
So class b, I made varsity, you know, freshman year and sophomore year. So I could glory days it up in high school a little bit, but it would be very fun to coach. So
James BenhamOh, I I bet it would be. And and, look, it doesn't matter your height. You can love basketball. It's it's it's it's harder to play Yes. If you're not super tall. But, you know, it's still you you can still be there are some ferocious folks play play basketball that, you know, might have been a little little altitude challenge that they still did great, but there's a lot of great coaching movies out there. The the you know, there there's a like, actually, there's some good coaching movies like, you know, Big Shot from Disney's Plus and then, like, Mighty Mighty Max with one of my favorites.
So, you know, it's good. You can get it you get behind that course. Texas A and M had a brilliant women's basketball team for a very long time, and our our old head coach just retired that won the national title in 2011. What? That's cool. So what led you into because you went to Gonzaga. So, like, when you when you left Montana and flew all the way out to Gonzaga,
Reghan Brandtlike, what what what were you what'd you initially study, and how'd you land in insurance? And I and I think you're hopefully being facetious, but some people think Gonzega is back east. It is in Spokane, so it's only a two and a half hour drive from Missoula. I know. I didn't I didn't didn't fly too far. But no. I mean I feel like I feel like everything in Montana is a long way. Yeah. Everyone's like, well, that's not where I'm like, no. It's only you you count the miles by minutes.
I'm like, it's only an hour, which is 60 miles. So, you know, it's pretty quick. There's not traffic, so it's easy. But no. I went to Gonzaga. I I had I grew up. I went to a Catholic high school, and so I thought kinda staying in, like, a Jesuit education, smaller school, close to home would be really fun. And then, obviously, the basketball program, Mark Fuze program, how can you not wanna be there, was so fun. I went to school when, like, Adam Morrison was there, Blake Step, all of those guys.
So it was just a total wild fun atmosphere. And when I got done with college, I was like, oh, now what do I do? I gotta be a grown up. So I got a job at Wells Fargo, which, you know, wasn't an insurance. I was slaying in mortgages. And I happened to be at a friend's wedding. And I had as we were talking about the painkiller drinks earlier before we started recording, we had a few too many cocktails at the wedding as one might have when they're twenty twenty four, 25.
And I met, an insurance agent who was like, you know what? You'd be perfect at premium financing. And I was like, I know everything about premium financing, a little liquid courage. And I'm like, trying to Google it the next morning. What the hell is premium financing? What is this? And the guy called me in the morning. He's like, come down for an interview. And I was like, alright, I'm just gonna fake this and see if I can land, you know, starting this company for this insurance agent.
And that was 2008, 2009. And that was the start of Columbia Pacific Finance. So you started it underneath another company? It wasn't underneath another company. It was three insurance agents at the time were sick of spending, you know, they're like, hey, we're giving this other company thirteen, fourteen points. And what if we can do it better? What if you can kind of find this, carve out niche with kind of smaller agencies? And so I was kind of like challenge accepted. Know, I bet on myself. I remember, you know, negotiating, talking to my dad, I'm like, should I negotiate salary?
Goes, negotiate, you know, ownership, see how much you can get. And I was like, all right, I'm going all in on the biggest piece of ownership and I will live off no money until we, you know, see how this works. And, you know, fast forward fifteen years later, we work with about 15,000 retail agents and, you know, it's still we're we're a smaller premium finance company, but it it's, you know, been quite quite the business and kinda opened a lot of doors for me. No no regrets on going all in then.
No regrets at all. Nope. So Yeah. And then and and, you know, premium finance is an area that a lot of us in insurance don't really touch. Right? You just work with a a third party, but I mean, it's necessary. I mean, absolute like, mandatory. You can't move product without it. Oh, yeah. And that was where when I started the first year, and luckily, I was 24, 25. I didn't have a boyfriend. I didn't have kids. I literally got in the car from, it was Seattle, Washington, and I drove from Seattle all the way through Wyoming and I stopped at every single farmer's agent's office.
And I would just pick their brain. How does this work? How do you do this? How do you know if you have to go outside? How do you know if you have to finance? How do you know what to collect? And I was able to see how their pain points, what they didn't like doing, know, why they didn't like using some of my competitors and you know, that kind of started the catalyst for getting everything going in the insurance niche. Did any of them become early customers?
Oh, yeah. A lot of them did. Yeah. We actually, we landed Farmers Insurance as a kind of company for their MGA that they have. So it was pretty cool. We actually helped so many Farmers agents and knew their pain point because that wasn't their specialty. They didn't have trust accounts because everything was handled through farmers and they didn't have different things for this outside kind of book of business that was new to them. So we were able to kind of help make sure they knew how that whole world worked if they were writing E and S.
James BenhamThat's amazing. That's amazing. And after after well, you still run that. You're still president of Columbia Pacific, but like me, one's not enough. And so you did you you you founded LostRunPro just in, supposed to be an easy way to, make LostRun process easy. You automatically generate and deliver a LostRun request. So, like, who who buys loss run pro, who uses it, and what exactly does it know, and, obviously, I think everybody on that's that's an insurance listener knows what a loss run is. My my software generates, like, billions of them.
So, I mean, you what what what what walk me through what loss run pro does and how you got to loss run pro from premium finance company. Yeah. No. Totally. So the funny thing is, and you wouldn't think of this as like a logical move from the premium financing, but back when the market soft,
Reghan BrandtMGA will release a quote contingent on getting loss runs in thirty days. And if you've ever met an insured, they never have losses. Oh, there's no losses. Right? And then all of a sudden, thirty days after you bind it, you have to actually submit the proof of loss runs and get these reports. Oh, they had claims. So then the pricing is going to change. They're going to cancel it. That was annoying on the premium finance side. I'm like, okay, now we got to collect this additional premium or this is going to cancel.
And so I really kind of early twenty twenty dove in and I'm like, tell me about this loss run to all my agents. I'm like, how do you get this? And they're like, don't even get me started. You know, you gotta call 20 different carriers. You gotta ask your insured to go do it. Like, it's literally, you know, this huge pain. And so I serendipitous, I'm kinda one of those fate people, but Payne West is in Missoula, Montana. I know we chatted about where we are here.
And they had just joined this group Broker Tech Ventures, which I don't know if you guys have heard of that. The 14 of the top 100 brokers kind of created this VC group. And so I saw it on my LinkedIn and I'm like, man, I should take you know, I have this idea. I wanna solve it. I kinda have it baked, but let me bring it to these guys. And I flew out. It was like a little shark tank thing and I pitched my idea and we got selected.
And by we, I mean, it was me. But I got selected and they give you a $50,000 safe note. But more importantly, they actually mentor you. So I had like, you know, Graham Company, m three, you know, all these big players at the time it was ADP on there doing it. And so I was able to kind of fully bake loss run pro within that year of having their mentorship of what it needed to really solve the pain for insurance agents. And how does it work?
So right now, we primarily, our bread and butter is to the insurance retail agents would use the platform and they buy it. And so if I was working on a new piece of business and I go to Tom's Trucking and say, hey, Tom's Trucking, I want to quote your insurance. I need three to five years of loss runs. And Tom's Trucking is gonna go, don't know how to Yeah. Get They're gonna go, what's a loss run? First, they're gonna say, what's a loss run? Yeah. Or they're gonna be even more awkward and go, so you want me to ask my current agent, let him know I'm gonna possibly cheat on you, but I may or may not be swiping left or right on you.
I'm not quite sure, but just give me this information. So it's a super uncomfortable thing, and so what we created was we have all of, you know, over 5,000 carriers, MGAs, and TPAs in the system. You come in, I'm doing Tom's Trucking, I'm just like, hey, they were with Travelers Cincinnati Amwins, here's the policy numbers. It sends per state regulations all the right disclosures authorizations to the carriers, gets this information back, and then we now have a lot of like add ons. So if you get this information back, a lot of these guys, to your point, you're creating a billion of these, right?
You get 10 different PDFs. Well, do I have a good picture of what my insured really is? We can actually ingest all of those and give you a standard view back with kind of the pretty charts. I call it the rainbows and butterflies, you know. Here's you have 10 claims and here's your highest incurred and here's where it's at. And so we streamline this whole process for new business for the agents, but we also handle their, you know, current business because on their current business, they're trying to get them ninety days before.
And what they're currently doing is working off a spreadsheet and a guy or a girl, sending an email, logging into a portal. It's just super time, you know, time consuming and expensive. And so we've automated that process for them.
James BenhamYeah. So they don't have to deal with the broker. They're going straight to the carriers. Exactly.
Reghan BrandtGetting lost. They're getting the lost ones direct from the carriers. Do the carriers ever notify the existing broker that Some do. Yeah. So we can't there's actually not regulation that, like, you can't notify, notify, but but they they can't can't not release the information to the insured. And I always equate this. There's still some carriers that try to play games or delay it, or I'm only going to give it to your current agent. And I'm always like, come on, dude. You don't want to only keep business because you made it so difficult to move.
Right? And data is powerful. It's like if I was going to get a, you know, an auto loan right now and someone's like, well, not going to tell you how good you paid on your mortgage. I'd be like, that's insane. Like they need to know this so that they can give me kind of an auto, you know, loan that I might need. And so that's the same thing in insurance. I think some of these carriers are starting to realize, like, this data is really the insured's, you know, information, and they should have access to it pretty easily.
James BenhamOkay. Really cool. And then before I hand it over to Rob, Rob, you know, always have to cover, but she's got multiple companies. I know. Know. I know. So so thank you for explaining LossRunPro. Thank you for explaining Columbia Pacific Finance. The other party, you're the chief digital operations officer for K2 Insurance Services. What is K2 Insurance?
Reghan BrandtSo K2 Insurance Services is actually like the fourth or fifth largest MGA in The United States, but it's a holding company, so you might not know the brand as well. We have about 40 companies underneath that umbrella in The US and write about $2,400,000,000 of premium annually. So it's quite the powerhouse. And it may seem like, how did you get into that role? Well, K2 invested in the finance company and then they also invested in loss run pro. And so as I was working with all of their different divisions, kind of pushing the financing, pushing the loss run services, all these different things, I started to kind of see some opportunities where some digital kind of new tools may help the MGA operation be more efficient.
And so they brought me in, kind of on the digital side to try to help improve some of those efficiencies too.
James BenhamYeah. You you and I have so much to talk about outside the show. I I I as well wear about three hats, and so there's there's there's a lot going on. But, you know, you can't help yourself. Insurance is like a beautiful candy jar that you just can't help but start unwrapping all the other candies when you see them. And so it's yeah, keeps you keeps you busy, keeps you alive. Rob, there's a lot to ask questions about. I'll let you take it from here. Yeah.
No. I appreciate it. So are we gonna you're
Rob Galbraithlike one of the, I guess, OGs, right, of this Insurtech world. You were kinda operating in this world before. There was even the phrase like InsurTech. So you've seen a lot. And I'm just kind of curious over the past ten, fifteen plus years, like what's really struck you in terms of this, obviously technology has been part of insurance prior to that, but you know, it's obviously gotten a lot of buzz. So I'm just kind of curious from your perspective, where have you seen maybe what I'd describe as real change, real momentum, and where do you think pain points still kind of exist that are frustrating to you and your clients?
Reghan BrandtI can be a little bit cynical, right? I feel like the InsurTech one point o was a lot of people who tech had great tech skills, maybe came out of the Bay Area, Silicon Valley, but they never were boots on the ground in insurance. And the hard part is insurance is so nuanced. It's regulated by 50 states. Every single person in the value chain has different needs. And so if you have this ego that you think you're gonna come in and just overnight, well, why can't I just get a database of all the, you know, claims history for every single company in The US and the London market?
That's just not going to happen overnight. And there's, you know, tech debt because of like older legacy systems. There's privacy concerns. There's all these different things. And so I think a lot of people came into the market being like, we're going to either replace agents or we're going get rid of this MGA, of these specialty things. And I think people then got burned, because they were like, oh, I'll go look at this whiz bang tool. And if it's the happy path, it works great. But if you know insurance, the happy path is not even 50% of the time.
There's always something weird and an edge case that throws out there. And so I think one of the things that, you know, I think I'm hopeful about is now with like Gen AI and different things coming down the pipeline, there's been this pressure on insurance that like, hey, you maybe were like, we don't need to do that because these guys really don't know what's going on and they're not gonna take it over Insurtech, you know, one point o, two point o. But now they're kinda starting to see like, oh, we could actually create some tools that really do improve our workflows and actually allow us to, you know, rate risk better, actually allow us to help our customers better, actually allow us to do loss control better, audits better.
And so I am hopeful that, you know, people are realizing now it's not like replacing, it's not getting rid of, it's not this huge kind of macro change. It's going to be more of kind of a, how do we actually focus on really what the insurance industry should be doing is mitigating risk for our customers, for our carrier partners, for our TPAs, you know, all those different things. And I think the new tools that are coming down, they're more focused on that. So, you know, I'm excited.
I think that that's changed the perspective of kind of, you know, InsurTech.
James BenhamYeah. I agree completely. Look, I started writing code for carriers and their service partner vendors in 2004. So it was a very you know, I I started this business in o one in my dorm room. Three years later, discovered I insurance, and I was a technologist. And then I've spent the last twenty one years learning insurance because, like, learning to code was easier than learning insurance for me. Because every every time I open another door, there's there's, like, not just a room, but a whole other building behind that door, you know, with hallways and and and and and levels and stairs.
It's it's it's really it's really complex. And I think as a technologist, I I do always start, especially now in the last two years because Gen a Gen AI has finally allowed me to solve some of the longer, harder problems that I couldn't solve before without it. Right? Like, just consuming basically, consuming nonstructured content has always been one of the biggest problems in technology development. So I I I I agree. I like now that a lot of the Insurtech nerds that I hang out with, Insurtech geeks out there, really do have a pretty deep understanding of insurance, and most of us have actually worked at an insurance company.
You know? And and, like, I've I've gotten to embed with a few of my clients and go and and dive deep at the carrier and at the MGA and the TPA and, like, really, like, really get to go in and and look at what does it look like to manage a claim? What does it look like to re renew a policy? What does it look like to quote buy and pay rate, underwrite, issue, renew? You know, all these transactions that occur in insurance. And so I think that's that's wonderful that that that you brought that that stack of tech.
What do you what I'm seeing now is that there's really no problem that we can't touch with with with the latest AI tooling. So what what are you seeing? Because you you generally work a little more on the distribution side, whereas I'm more on the capacity and and administration. So I'm curious as to what you see be the the big problems you say, man, I can't I can't build tech to solve this problem that you can now.
Reghan BrandtSo my thing is I don't think to your point, I think the tech, you can build anything now, and you can solve any problem. It's gonna be change management and it's gonna be the operations that have a culture and these people that are willing to just like push it through. So where I see the like hardest part for me right is we have so many skilled underwriters. We have so many skilled, you know, adjusters. We have so many of this. So much of it's in their head.
So I'll go, oh, okay. Let me help you on a workflow process. What are you spending all this time on? Well, I just do this, this, this. And they don't even realize themselves like the true workflow and the process that's going into it. And so sometimes you're so reactive in insurance because it's busy, you're making good money, it's everything's going well. I think it's gonna be hard to take that pause back for a while where things might take a little bit more time to really think through like what are the steps, How can I create a, you know, a bot or a tool to do some of these levels of it?
And that's where I see, you know, I think K2 has done a good job of trying to be forward thinking of like, how can we get teams in here to help maybe some of our legacy programs actually start moving forward? Because if they don't do that, they're gonna be sunk. Right? Other people are out there doing it and they have teams doing all of this. And so everyone knows you have to do it. It's just how do you actually mimic those workflows? Because your part, James, I mean, was laughing when you said that.
I I don't know much about the, you know, pricing side and the claims side and the fronting carriers, but that's now in the k two role I do. And so as soon as I'm like, oh, I made this widget for you so easy. Then they're like, oh, did you take in the cat the cat load and the this and the that? I'm like, what? No. Like,
James Benhamhow do you do all these things? You know? So Then you go,
Reghan BrandtYes. Literally.
Rob GalbraithWhere has this been my whole career? Rob? Mhmm. So, Reagan, I'm trying to think too. Obviously, you've got this background where you've built, right, tech and sold it. But now, I'm guessing in your role at k two, you also have this kind of build versus buy decisioning that you have to make. So, yeah, I'm just kinda curious, like, where is your head at as you see opportunities and what do you look for when you think, hey, there's an opportunity to partner? Like, maybe just walk me through your your mindset at a high level.
No, I definitely think like for K2, so we're unique, we're a holding company, right? And so we have 38, 40 different types of companies. So some are mobile home insurance and then some are kind of autos and very complicated propane risk. So there's not a one size fits all for a technology solution typically.
Reghan BrandtI am a big proponent for K2 of either partnering or buying versus building. I think you can just get there quicker and you can lean on some of these specialists to give you the product that you want. But you have to be able to actually, again, I'm gonna I'm gonna beat that drum all day long. Like deliver what you truly want. That's where I bang my head against the wall. Someone says, I want this Regan. And then I'm like, perfect. I made this for you. Oh, I want actually, I I forgot 10 steps.
Okay. So you want this. Oh, I really like that, but I need this again. Right? And so I think when you are evaluating software, sometimes that shiny happy path can be like, oh, this is really great. But how do you actually decide who's gonna own the project? And I think that's huge. A lot of people don't have an owner for a lot of these projects. Who actually owns this? Who actually is measuring it? And even if it's a big company, that should just be one person in my opinion for each project.
You can have multiple people helping you, but you need one representative kind of owning it. And so I think when we're looking at it like who's the owner? What's the outcome we want? What's the ROI we're gonna get? And what really is the workflow that we're trying what's the pain we're solving? Cause sometimes just to be like, that looks cool. No. What are you really what's the pain, you know, in doing that? So, you know, from my lens, especially with K2, the buying makes a lot more sense, but you have to be smart about how you're buying it and you have to be really diligent about the process to make it succeed.
James BenhamYeah. There's almost no one reads specs that you write, and then we actually stopped, in a lot of cases, producing them because we can now now we can use some really good AI tools to just build a fully functional prototype and send that to them because they'll actually click through that. But even Yep. If it if it if it doesn't have their production data in it, they won't spend the time in it. So, like, we're we're kind of jumping past we'll do a requirements list. We'll feed the requirements into an AI gen tool that'll build a a real time, you know, fully functional prototype, and then we present that.
And then when they're when then they'll they'll they'll review it usually, but they won't review it in-depth enough. So we're still having the case where when we feed that in a cursor and have it build the production code, we slap it on a production database and they get their their data and their app for the first time, then they'll do maybe 80% review, and then there's still that last 20% they don't look at until they go live. Yeah. And and then you spend, you know, usually a whole sprint, or two after go live, fixing all the things that you would have wished they would have caught back in the prototype phase or in the initial, you know, user acceptance testing.
And and Totally. And and I don't I don't think there's I'll be honest, Regan. I don't think there's a solve for this. I've been writing code since I was 11, so I'm 46. So thirty five years now. I Yeah. I don't think there's a solve. I think at the end of the day that people
Reghan Brandtare gonna save the most critical feedback for the very end when it's live. Oh, totally. Totally. I think my my push on that would be getting the like, a smaller group because I also see this, like, analysis by paralysis. Right? You get a group of 20 people looking me. That's too many people. You need a couple people in the room who know enough about what's going on and then if they need to go talk to the experts who are writing it or working on this. But my push is like at least know what you what you're solving for and what you want the outcome to be.
And I think sometimes people who are buying software don't even know that you know and that's where my my recommendation is making sure hey what is what is this ultimately solving for you? Who's gonna be using it and how are you gonna implement this you know in real life so that you can get even if it is the sprint afterwards, who's gonna give you that feedback then versus they stopped using it and they said, it didn't work. It's like, no, you just didn't utilize it. You know, there's there's a difference there.
James BenhamYeah, there is. Rob, any wrap up questions?
Rob GalbraithYeah. Just what what are you kinda looking forward towards the the future? You gonna obviously, you kinda mentioned Gen AI, and that's been obviously a big theme on the podcast over the last year in particular or so. So, you know, is is it more just like working with that or is there other new technologies or new opportunities that you see out there for the future that get you excited?
Reghan BrandtYeah. I mean, I think one of the things that I kind of pride myself at LossRunPro, right? We focused on one thing and to be the best at it, have the best reputation, solve the problem the best. And, you know, now we have the trust of a lot of these agents and distributions who use us. So it's like, what else can we send down that pipeline that saves kind of solves some of these pain points for them? So that's what the team's kind of been involving now.
Okay. How can we pull in their border rows of claims data? How can we look at their, you know, different loads? How can we now maybe put this in a submission for them? And so I think once you get the trust of customers and that they know you're always looking out for them, you're willing to learn, you're willing to put your ego down if it's like, hey, this didn't work, but you guys need this and kinda work together. So I think this year, I'm just excited because you know, now having Gen AI, you can code so much faster, you can bring products to life much faster.
And so if you're always doing the right thing for your customers, I think that now having these tools, the sky's the limit. Awesome.
James BenhamWell, look, it it's we're gonna we're gonna end on the sky's the limit because I agree with you, especially when you got a big sky like Montana. Right? Exactly.
Reghan BrandtExactly.
James BenhamRegan, thank you so much for joining us today. I really appreciate. I really appreciate your mindset, your hustle, the technology you're building, as well as the the insurance companies you're helping to build from the great state of Montana and all over the world. Yes.
Rob GalbraithAnd Rob, as always, thanks a bunch. Yeah. Pleasure. Off to a great start here in 2026.
James BenhamIt is. And thank you out there in listener land for joining us for another great episode of the Insurtech Geek podcast. We got to geek out with Reghan Brandt from k two insurance, Lost Run Pro,

