
Insurance Town · 2026-07-02 · 55 min
Key moments - from our scoring
Substance score
31 / 100
Five dimensions, 20 points each
Heath and Caleb discuss how AI has evolved from reactive tools (like ChatGPT for search and learning) to proactive, agentic AI that works autonomously in the background. Drawing parallels to the dot-com boom of the 1990s, Caleb argues we're still in early innings - similar to when the Internet was just about finding nearby McDonald's locations. The real value, he suggests, won't come from asking "what can AI do?" but from identifying specific jobs to be done and which people benefit. He emphasizes that agentic AI tools like 1Fort AI can automate low-skill tasks (quoting, proposal building, email monitoring) while freeing skilled staff to focus on high-value work. Heath adds that successful agencies are already combining AI with human touch - using AI to identify prospects for personalized postcard outreach. Both speakers stress this isn't about replacing advisors, CSRs, or producers, but augmenting their work. The episode touches on broader cultural shifts: a nostalgic move toward analog (flip phones, vinyl records, print magazines) alongside tech adoption, suggesting companies that identify the right "jobs to be done" will extract maximum value.
Reactive AI requires user prompts (like ChatGPT search for information), while proactive AI works autonomously in the background without prompts - monitoring email, websites, and data to automatically quote markets, build proposals, and handle tasks.
No. AI and humans are complementary; agentic AI automates low-skill tasks (quoting, data entry, email triage), freeing VAs and staff to focus on higher-skill, relationship-based work that AI cannot replicate.
Like the 1990s Internet (which people only imagined as search), today's reactive AI is scratching the surface - the real value will emerge as we move beyond the hype to ask what specific jobs AI can solve for individuals.
Forward-thinking agencies use AI to identify prospects (via geofencing, event attendee lists) and personalize mail, proving that technology can power the human touch rather than replace it.
Instead of asking what AI tools can do, identify the specific jobs to be done in your business and which employees will benefit from automation, then select tools that excel at those jobs.
Our reviewer’s read on each dimension, with quotes from the episode.
There are a handful of genuinely useful conceptual frames - reactive vs. proactive AI, deterministic vs. probabilistic stitching, the 'jobs to be done' lens applied to insurance workflows - but they're buried under extended ad reads, personal anecdotes about kids and flip phones, and nostalgia digressions that consume the majority of the runtime. The ideas-per-minute ratio is low.
the teammate that is Heath, Sharon that is just sitting around waiting, and I have to tap you on the shoulder to ask you something that's not an awesome teammate
the companies like us, we're going to have to get pretty good at stitching the AI. The probabilistic to the deterministic
The reactive-vs-proactive AI framing and the deterministic/probabilistic stitching concept are moderately interesting and applied specifically to insurance, but the dot-com bubble analogy is well-worn, 'jobs to be done' is standard Christensen, and nothing rises to genuinely contrarian or first-principles thinking.
we still basically the reactive version of the Internet was not the valuable part of the Internet
we'll stop asking what can it do? And we'll start asking like, what. Who can we serve? And what. What jobs are to be done?
Caleb Kramer is three months into a sales/GTM role at One Fort and is appearing in what is explicitly a sponsored episode; he is not a practitioner who has operated an insurance agency at scale or built the product, limiting his authority to informed vendor advocacy rather than operator experience.
I'm in my third month, so it's like in Caleb and dog years
Somebody smarter than me is, um, in charge of our security
The episode delivers some concrete product details - SOC 2/HIPAA compliance, private OpenAI and Claude instances, GWP-based flat-rate pricing, 30-day money-back guarantee, CSO from Coalition - and names real use cases like ENS accounts and accord generation, but the flagship '80% reduction' claim is stated without a source, and no customer names, revenue figures, or external case studies are offered.
our chief security officer was the first engineers at AT Coalition
we are not storing anything that is not only not, not insurance related, we're not even personalized stuff
The host explicitly hedges a challenge with 'me carefully ask this. I don't lose a sponsorship right now on this call,' which signals the commercial ceiling on probing; most questions are leading or invitations to pitch, and the conversation drifts repeatedly into personal stories, 80s music, and flip-phone nostalgia with no recovery mechanism.
me carefully ask this. I don't lose a sponsorship right now on this call
What are some of the biggest pushbacks that people might have had with one for it so far?
Computed from the transcript - who did the talking, and the words that came up most.
Most insurance agencies are still using AI like a search engine. They open ChatGPT. They ask a question. They get an answer. That’s useful. But it’s also reactive. The next generation of AI doesn’t wait to be told what to do. It monitors activity, organizes information, surfaces opportunities, flags missing data, drafts communications, and helps move work forward before anyone even asks. That’s the difference between using AI as a tool and working alongside an AI Digital Teammate . In this episode of Insurance Town , Heath Shearon sits down with Caleb Cramer of OneFort to explore how proactive AI is reshaping insurance agencies, commercial insurance workflows, and the future of agency operations. Together, they discuss why the conversation around AI needs to move beyond chatbots and prompts toward intelligent systems that actively support producers, account managers, and agency owners throughout the day. From commercial submissions and renewals to proposal generation, risk assessment, and customer communication, this episode provides a practical look at how AI is becoming an everyday teammate for insurance professionals.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Ladies and gentlemen, welcome to Insurancetown. You're here. You've made it. You arrived. You made it here. I'm so glad you're here. You clicked on this episode obviously because you wanted to, uh, check out this one. Probably because I mentioned Caleb somewhere in there and you were like, oh, I got to see this one. So glad you're here and I'm pumped you're here because this give me a fun conversation with my brother Caleb. So I've asked him to be quiet for just a minute while I do my ad reads. Um, guys, as you know, I couldn't do this show without my sponsors. I love them. You love them. And I'll start in no particular order with my good friends over at Canopy Connect. They've been with me since day one and they are the one click solution to getting the deck pages you need to quote prospects. But more than that, you know, they help you to take that data that you get. That data intake platform that they have is phenomenal. And they also have a way now called Trailhead where you can kind of design your own experience for your customer and help them to get that information to you the way that you want it. And that's easiest for them. So check that out with Trailhead. Go to use canopy.combackslash heath and get your discount, get your demo, do all the things. I love them. They're a game changer, good friends as well. And um, also I got a new sponsor. I wish I was air Horns Caleb. I've got a new sponsor in Veeva. And uh, they're not just your typical VA company. Agencies are going to them because they're insurance trained. Some of them times they have licensed uh, VAs that can help you with some of that kind of stuff. They can help you buy and they can help you do some of those types of things and they help you to manage the capacity services and do all the things, you know, reclaim 20 plus hours a day by offloading those quoting and policy servicing tasks to a VA. Go to to vivavs.com and check them out. Tell them the mayor sent you. And then, uh, lastly, but definitely not least, uh, my good friends over at 1 Fort Caleb, you want to jump in here? I've got you here. Do you want to do the live ad read? Give me a 30 second elevator pitch for one for it.
Speaker B: Yeah. So, uh, if you've heard of AI, we uh, one one for it is your AI digital teammate that's vigilantly watching your email and your front door of your website. It can even Take an information from Canopy Connect, uh, and taken all that information and go quote your markets for you, build proposals out for you and hand your high skilled staff even your Viva vas stuff. That's 8020 for them so they can continue doing high skill stuff and they're not stuck in death by a thousand clicks land.
Speaker A: Love it. Go to One Fort AI, that's the number one Fort AI and check it out and tell them the mayor sent you so they know that you came from the show and they'll treat you really nicely. Guys, uh, I can't wait. Uh, he's already, you've already heard his voice. He's already here. Look at that gorgeous hair. If you're watching on YouTube, I'm always hair envious. I have hair envy every time you come on the show. I got to grow my hair out a little bit more and get some, some better hair. Caleb, get on in here. How are you brother?
Speaker B: Doing good, man, I'm doing good. Um, I get to go to Key west tomorrow, hang out with uh, David Carruthers and the cool event that he's put on. Yeah, I think this is maybe his fifth year now doing it. So the kinks are all worked out. Um, and it's going to be a great time.
Speaker A: Dude, that's gonna be so much fun. I got to go a couple of years ago and absolutely loved it. I think I went twice. It was so much fun. I forgot I was an insurance event. It was so cool.
Speaker B: In the best way. In the best way. You forget you're at an insurance.
Speaker A: Yeah, yeah, of course we're all talking, you know, we're getting better, we're all pushing each other but the conversations we're having, you know, it for people who don't know, you're like, oh, it's a bunch of people just looking for excuse to go to Key West. No, it is. But at the same time you're talking to people that are in the same world as you and you're able to share ideas and talk through things. And you know, most of these producers that you're going to meet there, uh, that are in this environment are high level producers and they're producing accounts that, you know, maybe you want to be like them or maybe you have some ideas you can share with it. It's, it's really cool. I hate to give a too much of a plug and shout out to my boy Carruthers, but I love him and I, uh, think it's really cool. So if you're, if you're not Going this year. You got to look into it next year, man. It's super cool.
Speaker B: Yeah, no free ads, but is, um, right. Um, and because of that, um, only downside, I'm going to be missing my soon to be 10 year old's birthday. I'll be there.
Speaker A: So.
Speaker B: So we put a bit of a pin in it today and we got to go and feed the drabs and went to the zoo and had had a little three hours zoo day this morning, so that's awesome. So it's always good to get out and, and yeah, boxes, you know, so.
Speaker A: And it's good to know that you have a good boss that allows you to be able to do that and your team is able to cover for you while you're gone. Checking out the.
Speaker B: Yeah, Toby's finding out about it right now, so.
Speaker A: Oh, good. There you go. Um, that's awesome. I'm sure he was able to pick up all the demos and all the conversations and all that good stuff. That's cool.
Speaker B: So how are you?
Speaker A: You good, man. Life is good. Um, you know, everything's going well here in Insurancetown and we got a new sponsor on the show, so that's exciting and you know, just trying to look for opportunities and I get people. Uh, we'll start.
Speaker B: Why not?
Speaker A: Um, people talk to me all the time about this idea that AI not only is going to replace their people, but there's no need for VAs anymore because of AI. There's no need for service staff because of AI. There's no need for this. Like AI is going to disrupt and replace everything. And I completely disagree. And so I still get DMS and emails and text message from people asking me about VAs and what my thoughts are and should they still have them or virtual assistant or you call them virtual executives. Virtual. I've heard them all, all the different titles for them. But I still think there's a huge need. And so, uh, whenever Rob reached out to me about sponsoring, I was like, yeah, let's do it. And so, uh, it's a long time coming. He and I have been discussing this for a minute, but I do still think there's a huge need for those virtual assistants and they could be using AI in the background. They could take some of those tasks off your plate and even be better virtual assistants because of AI.
Speaker B: Yeah, I completely agree, man. Um, supposedly, uh, AI is coming for me too. So it's coming for all of us.
Speaker A: It's coming for all of us. But you know, pretty soon there'll be AI podcasts where they won't even need me anymore. They'll just be able to use a voice and, you know, record podcasts without an, uh, actual host. But, you know, hopefully my audience won't get to that. Or I could just change up. Welcome to Insurance Town. This is your VA or your AI Podcast host here. Heath, Sharon, Caleb, how are you today?
Speaker B: You'll just end up pausing like me, you know, glitching.
Speaker A: Uh, for those that don't know, I give Caleb a hard time because he's so thoughtful in his talk that the last time he used his speech patterns, that last time he's on her, I had to spend four hours editing just to get it to a normal speech pattern. So instead of that, I'm gonna go ahead and just tell you guys now. Listen to this episode on 1.5 and you won't notice a difference.
Speaker B: Well, AI is great at that, at, uh, editing. So they are.
Speaker A: They are that maybe I can hire a VA from Viva to just edit my podcast for me.
Speaker B: Boom, boom.
Speaker A: Perfect. Okay, so let's talk because you. You've been on the show before, and I've had Toby on, um, from one Fort before we had the sponsorship. But, um, you know, you're still somewhat fairly new over there at one Fort and tell me.
Speaker B: I'm in my third month, so it's like in Caleb and dog years like this, you know, we're. Yeah, uh, this is midlife crisis as far as, like, how Caleb beers go, you know.
Speaker A: But here's the thing, and we could edit this out because I'm gonna do a lot of editing anyway, but I feel like, because you and I have had these conversations, even probably on the show before, of, like, you like this startup land. You like the fast pace, the change, you like that kind of thing. But I feel like you may have found, like, a forever home.
Speaker B: That's fair to pick up on that. And what does maybe feel different is a pretty cool intersection of what I naturally care about. Um, and I get to have that impact on a product that is very much intersecting with what I care about and what my competencies are. Um, and I get to serve the people that I care about in this industry, where I think the one constant that I've felt for the past, I don't know how, going on 10 years, um, selling into this space. It's. Other industries take for granted having tools, uh, a tech ecosystem that this industry would kill for, um, and they take it for granted. So I love just finding awesome bits and pieces to introduce into this space. Um, and this is the latest awesome piece to introduce.
Speaker A: Yeah, it's good timing because again, AI has been around for a long time, but this.
Speaker B: What's that A.I.
Speaker A: right? Um, artificial. I think it's intelligence. But no, it's been around obviously. But now since the whole, you know, chat GPT thing in 2023, you know, really, I, uh, think it's changed the way we look at it, the way we understand it. And now we're getting more into this agentic, uh, you know, how it takes it a step further and you know, I, I like to talk about it in a sense of proactive versus reactive. And you and I had this conversation, um, recently on a webinar and I, I loved it. And the more I've thought about it and uh, I've had some response from that. I think there's a lot to be said there because it's. Again, when it first came out I was like, all in. You know, and I was like, what all can I search? What all can I find out? What all can I learn about? Because now I've got the whole. I mean with Google we had the whole Internet our fingertips, but now I feel like we really have it all. Like it. With the generative AI, it could search everything. And so I was like learning all kinds of stuff and deep diving into anything and everything I could. And again, that, that was incredible. But I feel like that was more of a reactive, like you had to prompt it to get it. But now we're seeing AI can go a whole different. Like it can now do things for you, it can now be working for you at all times. It's like you truly have a. Another employee, so to speak. And not to replace employees, but I hate to say it that way, but you know what I mean? Like, yeah, with so many, I don't know, I feel like anytime you say anything, you have to like, qualify or uh, quant. What's the word I'm looking for?
Speaker B: Yeah, qualify qualifies, right?
Speaker A: Is that the right word? But again, you know what I'm saying, Like you feel like you have something working for you at all times now.
Speaker B: Yeah, I understand your need to be careful, but I, it still feels like early innings to me. Um. Oh yeah, you keep hearing about AI Being a bubble, right. And so I've been doing a bunch of deep dives into the dot com bubble and what that was, uh, where the similarities are. And there's something about this reactive, chat heavy version of AI M that feels like 1995, 1997. Holy cow, Heath, look I'm able to find all the McDonald's around me on search.
Speaker A: This is crazy.
Speaker B: What I can, uh, find what I can seek out from the Internet, right? And at that point, because the only thing, the only constant is we have a failure of imagination. And so at that point we couldn't see that the Internet was something other than search, right? Like, it's hard for us to know that, you know, not only, like, was it going to enable finding all the McDonald's around us, but also,
Speaker A: uh, powering
Speaker B: the app that could go power the courier that could then bring it to our house, right? So like, we had a failure of that imagination. So like, what are we failing to imagine now? And we are still basically the reactive version of the Internet was not the valuable part of the Internet, right? It was just scratching the surface. So I think we're just scratching the surface. Um, but even with those leaps and bounds, we still have humans around. We found our place in the world. Right? Um, and so I think the one thing that did happen that is like, uh, uh, another phase that we're at right now is we don't. It was Amazon.com and everything.com, right? It was very.come and then all the newspapers were like, you know, you gotta use the Internet. It was very, very hypey. Like, you gotta use the Internet. If you're not on the Internet. Like, you're, you're screwed if you're not on the Internet. Are you using the Internet, Heath? And like, it's still kind of, it's silly now to think back and like, heath, are you using the Internet? Like, what kind of question is that, you dummy? Like, am I using the Internet? I think we'll think back on AI as the same thing because it's not just searching for what is this disease that I have that is one of my primary functions of using AI.
Speaker A: Right.
Speaker B: Yeah, um, it's, it's valuable, it's better than WebMD. But that's, that's not where, yeah, this value maxes out. Right?
Speaker A: You, you bring up a good point. And I think it's interesting that you, you compare because I hear that comparison a lot. When we go back to the dot com boom in the 90s and going through all of that and everybody had to have a website and all of that, and then how long it's taken, you know, um, for us to really adopt, to get on board. And there was several years people were still scared of it, yada, yada, yada. And it took a good while of that whole Thing. And then now people are starting to compare generative AI and agentic AI to that. But I'm wondering now, as you say, that are, uh, we in too much of a hurry to sprint through to get to the next phase? Because it took a while, I feel like, to get from reactive Google search, whatever it might be, to social media to where, you know, now you can go on a website order package and it comes to your house, that kind of thing. But I feel like now maybe we're sprinting too fast or in a hurry to say, okay, now, what else can I do? You know, now once we get to agentic AI, I was like, okay, now, now, what else can we do? How can we push the text? What's next? What's next? It's like, can we just chill out and enjoy what we have?
Speaker B: Yeah, I think, I think what. I, uh, I hope I may have
Speaker A: lost half the audience, but it will. I know.
Speaker B: I. Well, I like nerding out. Um, yeah, these are important questions. Um, so I think one thing that we'll see is we might see a bunch of the. Right now we've seen, uh, if you've walked insurance trade show lately, you've seen every booth go from name to name, plus AI name, AI.
Speaker A: Right, right, right.
Speaker B: So I think we will get to a point where the, the businesses with good fundamentals and good points of view, we'll revert back to, like, we'll go from our Amazon Amazon.com to just. We're back to Amazon phase, where, yeah, no one says Amazon.com anymore. Um, I think we'll ride that wave. And then I think what we'll do is we'll stop asking what can it do? And we'll start asking like, what. Who can we serve? And what. What jobs are to be done? Because AI is just really freaking cool software. Right? And the best way to use software, the, the valuable way to use software is to identify jobs to be done that liberate real individuals and people from doing jobs that they don't want to do or they are, uh, are, uh, below their skill level and just turned into loose. And then, um, that's how. That's how you get Main street companies, Main street agencies to extract a ton of value out of it. But I think we'll have to start asking what, what jobs are to be done and, like, articulate that once the hype dies, we'll actually have to say, all right, I understand your business. These are the jobs to be done. Here are the jobs that my tool can really, really knock out of the park for you. And these are the four individuals that will reap the benefits, right?
Speaker A: Yeah, no, I'm with you on that. Uh, I just, I hope that we're not rushing to the next iteration and rushing through. And sometimes I just want to, like, pause and just be like, okay, let's enjoy generative AI for a little bit longer. Let's enjoy agentic AI. Like, it's great now. It can work in the background for you. Now I could be doing things without being prompted. Now I can automate and do all these things without being prompted. Can we not just rush to the next thing? And I remember for years, um, I was so afraid of the future because of Back to the Future, for example. Like, I didn't want flying skateboards and all of that kind of stuff. Like, that's stu. I don't want all that. You know, I just want to enjoy what we do have. And like, at that time, I remember thinking, man, it's so cool that I can be in chat rooms and talking to people. I've never seen their faces. I don't know who they are, but they're in a different. And I can talk to these people from my computer. I didn't want it to rush to the next thing. And I didn't want to have flying skateboards and be able to go into the future with a stupid DeLorean. And I didn't want all that. And now I'm in that same boat.
Speaker B: You're like, hold up. I'm still trying to think of the perfect away message on aim, you know?
Speaker A: Yeah, I'm still trying to decide if I'm going to tell people in chat that I'm a buff, you know, whatever, or if I'm going to. I'm a super nerd. I don't know. I'm just. Because nobody knew. But anyhow, I just. I wonder. But I will say I am seeing, because you and I, you've got. You said 10 year old. Um, I've got teenagers, um, and I am seeing my teenagers now. There's some of their friends that come up with flip phones or they'll come over and they're like, going back to this nostalgic era, so to speak, of, like, we don't want all this in our face all the time. We don't want to have the screen times all the time. Like, they think it's cool to have a flip phone. Crazy.
Speaker B: Yeah. Uh, there is a move back to analog and back to flip phones and dumb phones. They're calling them dumb phones. Yeah. Yeah.
Speaker A: Which I think is cool.
Speaker B: Which is interesting. Yeah.
Speaker A: Um, because at one point I remember, you know, two or three years ago, um, my son. I guess it was probably 13th or 14th birthday, and he had a bunch of his friends over, and I was making fun of him because I looked up and every one of them were sitting in the same room on their phones, texting each other and, like, showing each other, oh, check out this reel I just saw. Or look at this. Tick tock. And I'm like, put the phones out and freaking talk to each other, you goobers. But. But now I'm like, okay, this is cool. Now they're like, oh, we like the dumb phones. We like having analog. We like this. And they're watching, like, 90s movie movies and 80s movies, and they're listening to 80s music. And my daughter's huge into 80s music right now. I was listening to Duran Duran the other day.
Speaker B: I was like, vi, vinyl's making a comeback.
Speaker A: It is.
Speaker B: Yeah.
Speaker A: It's so cool. Um, it was funny. I was at Target the other day with my daughter, and they had these mini vinyls, and it's just one song. I'm like, it goes back to the CD singles that you just come out. And I was so excited, I had to buy the whole album. I just buy the CD single. My favorite song.
Speaker B: Yeah.
Speaker A: And, um. Crazy. Do you remember what your first CD was? We're going into squirrel land for a minute.
Speaker B: It might have been Green Day.
Speaker A: Okay.
Speaker B: Yeah. Thinking.
Speaker A: But no going back to this conversation. I do think it's interesting, and I'm wondering, you know, if we're gonna see more of this. Maybe it's a level set. Maybe it's, um, you know, coming back to center a little bit where we're gonna see. Because I'm already seeing print coming back. Like, I'm seeing people using, uh, mailers now and, like, postcard mail outs. And it's like, okay, this is cool. You know, even with the. The growth of AI and the growth of all this, we're still seeing people want the human touch. They want that handwritten card. They want. You know, you see in some of that, too, or maybe it's just Arkansas, but I feel like I'm seeing that across the country.
Speaker B: Yeah. I'm seeing more and more. Like, like, more curation, more meaningful curation. More. More things that are hard to replicate. Like, Matt, like, print magazines are coming back, you know, like $20 a month print magazine, prescription subscriptions. Right. Yeah. Um, Yeah, I think,
Speaker A: uh.
Speaker B: I think the. The dumb phone thing is is interesting to think about. Um, it's the. All right, what. What is this thing supposed to do for me versus, like, all the things it's became? It's become all the things that I am now able to do on this thing versus, like, oh, if it's down to its essence, it's supposed to connect me with the people I'm supposed to be able to do this. Let's knock it out over our skis with products. Um, let's do certain things really, really well. Um, I saw something a while ago where it's like every complex thing that works, like, started as a very, very simple machine that, that worked.
Speaker A: Yeah.
Speaker B: Um, and like, I thought that was interesting because, um, and then. And then the complex thing gets too complex and then, like, it like, doesn't work.
Speaker A: Yeah.
Speaker B: Um, so I don't know where that. Where I'm going with on that journey, but, um, it's wonderful.
Speaker A: Uh, I do think, you know, regardless of what I always come back to on this show and in my life in general, I'm m. M praying to God I'm always right on this. Um, but I feel like no matter what, we're always going to be a relationship business, you know, whether it's smartphone or dumb phone, whether it's digital or print, whether it's this or that. And I think there's always going to be a need for that advisor, that csr, that producer, the whatever you have in your. I think there's always going to be a need for that. And I think again, going back to the example of the. I, uh, was talking to an agency Monday. What's today? Wednesday or Thursday? Anyway, Monday of this week. And they were telling me about how they're using postcards or whatever, but they were using AI, you know, to. To find the people to send them to. And they were using geo. Is it Geo Traffic. Geo, whatever it's called. But anyhow, where they were putting a pin around an event they were at. I think it was fai, but they had a pin. They were going to find all the agencies that were in that, that were there, whatever it was, and they were going to send out a postcard to say, hey, good to see you. So they were using AI to power the human touch. I think that's. I think you can have both in the same sentence. And they don't have to be one or the other.
Speaker B: Yeah. They can be complimentary.
Speaker A: Um, Thousand percent.
Speaker B: Totally agree. Um, I think, yeah. How do you make people feel special? Um, and AI can be, ah, a WD40 on the machine that tees you up to do uh, the hard thing, the last mile, hard thing to send, the thing that really can't be replicated. Them opening that package that makes them feel good. The thing that you can't fake. The thing that, you know, they, people want to feel like they're, they're, they're so sick of being on like one out of 500 people on an email list that they want to feel like, oh, like I'm maybe 1 of 1 of 10, maybe 1 of 1 of 50 that got this. Um, and AI can help identify sort like um, and even point you in the right direction. But like, yeah, I think we'll have to find ways to make um, people feel special. Right.
Speaker A: 100%. I think, you know where you could use some of that again with AI is I could probably do an AI search, general search on Caleb Kramer and probably find out your kid's name, your dog's name, your wife's name, where you live. Like find out those kind of things to make it personal, to be able to say, hey, how's Fido? You know, and what, whatever your daughter's name is, I should know, we're friends, but I don't. You know, what'd you do for her birthday? Did you have, you know, a party job, a sleepover? Did they have, you know, braiding hair and pillow fights? What were they doing in 10th birthday? But whatever it might be, yeah, you know, I think you could make it where they feel special, like oh Caleb, remember my name. You know, he, he knew about my 10 year old, he knew that we had a birthday. Like I'm sure all that could be found in a 10 second AI search. I'm sure if you have enough of your personal information out there, but, or for that matter a commercial account, you could probably find out how many employees they have, how many of this, what's going on with that, you know, get their loss history, get all that kind of stuff and um, be able to make that personal them. And so when you're talking to them, you don't have to go through the back and forth of all the questions and all the things. It's all right there. So then you can get into the building relationship, you can get into the conversations and you know, I think that you know, goes into this thought process and the research I've been doing on having digital teammates, you know, where you get to uh, deploy some of those things to power those producers to have those personalized feel special conversations.
Speaker B: Yeah, I think um, the digital, when you first Told me about the digital teammate thing. I've been noodling on it ever since as well. I think it's interesting framing and it. And it. It works because I need to hurry
Speaker A: up a trademark it.
Speaker B: Yeah. Uh, and that's the version of A.I. uh, that's exciting. Right?
Speaker A: Yeah.
Speaker B: Right now, reactive A.I. is. Nobody really wants the teammate that I gotta be always on teams like, Heath, start this, do this. Or what do you think about this? Like, yeah, the, The. The. The teammate that is Heath, Sharon that is just sitting around waiting, and I have to tap you on the shoulder to ask you something that's not an awesome teammate. Right. Um, the answer is, better be knocking it out of the park if I do tap you on the shoulder. But I think what we think of when we think of teammate is, all right, I can trust it. Heath is doing XYZ and doing it well even when I'm not asking him to do stuff. And then I can turn around and ask him for more context or give me insights on what you've been doing. Right. Um, based on what you've learned while you've been doing X, Y and Z. What should I do about A, B and C? That's. That's a collaborative teammate. And I think that's what's been unlocked recently with AI. Um, which is pretty cool. And back to the AI is just really freaking cool software. It's not just one thing. Um, and it shouldn't be pointed at all jobs to be done. Just like you have a creative side and you have a side that, um, is disciplined. Maybe both of those sides aren't equal.
Speaker A: Right.
Speaker B: Maybe you have things that you trust yourself with or your wife trusts you with that she doesn't trust. Maybe she'd rather trust herself to do some things. I know I've got a list of those things. Um, same thing with AI And I think what AI being probabilistic, meaning you give one input and you're going to get a pretty consistent grouping of outputs from that. But they're not all going to be the same versus deterministic, which is one input, you're going to get one output. Maybe when it comes to my accounting or my systems of record, I want more deterministic than probabilistic. You know that that teammate is going to have two sides of the brain. Right. And so the, the companies like us, we're going to have to. The ones that win are probably going to have to get pretty good at stitching the AI. The probabilistic to the deterministic. Those Stitch those two sides of the brain together so you can have a digital teammate that can be relied on and can do the creative. Okay. Like, make sense of this. I don't have all this stuff nice and formatted for you. Go use the probabilistic side and go make sense of it for me. Right. Um, those two things need to be in concert, and we've kind of been talking about them up until this point, like, they're separate. And so that's why I'm excited about this moment in time.
Speaker A: No, I completely agree. And it's funny you brought up the family part of it, too. Like, talking about the wife when I made me think about, you know, m. You know, my son's 18, going off to college, whatever, but he. He figured. Took him long enough, but he figured out over the last year or so. Um, you know, because my. I have two daughters and a son, and my. My daughters were always so jealous of my son. Of, like, you're the favorite, you know? You know, mom loves you the most and does that and the other. And they finally. They were having this conversation at dinner, and he was like, I just figured out the cheat code with Mom. You know, I figured out what to do. And they're like, well, what. What's the cheat code? What is it? It's like when I come home from work or from school or whatever, I spend the first 15 minutes picking up something, doing something around the house, folding laundry, putting up dishes. Just 15, 20 minutes of just little things around the house. And mom's not pissed at me. You know, things are done because mom doesn't have to do it. She's not tired, she's not frustrated. She's not yelling at me. Hey, you know Reese. That's his name. You know, Reese, did you pick up your laundry? Did you do this? She doesn't have to do that anymore. You know, she doesn't have to come in and be pissed off because there's the floor that had to be swept or there's, you know, dishes in the sink. It's like, all I do is it's 15 minutes, and it makes mom happy. And, you know, she was like, it's not a cheat code. It's just, uh, the right thing to do. And it made it. To your point, it made him a good teammate. He was always looking for something to do so that he could focus on what he wanted to do, which is spend time with his friends or go out and, you know, hang out with his girlfriend or not get yelled at by mom, you know, and it's like to me it's kind of like where AI is, where you could deploy AI to be working for you, doing those little things that take like four hours for you, but you know, it takes them 15 minutes. And then that way your producers, your staff, your CSRs, they could be doing what they want to do, hanging out with their friends or whatever. But you know, they could be, you know, networking, they could be going to the events, they could be, you know, whatever it might, advising clients. They could be doing the things they want to do. But it was like, it was just funny and again, I haven't worked out that analogy in my head so hopefully that made sense to the audience.
Speaker B: But I like it. I'm gonna. And I, I could learn from Reese. Uh, totally.
Speaker A: But it was just as you were saying that, you know, talking through that I was like, yeah, that's exactly what a teammate is. You know, a digital teammate. If you're a producer and you could instead of spending an hour researching clients and figuring out all the information you need to figure out before you walk in a prospect meeting, put together, um, an agent that goes out and does that for you. So all you got to do is just type in the name one fort AI or whatever and then it goes and tells you everything about one fort. Who the founder is, when they started their company, what are their pain points, what are this. That uh, they could do all that for you. You know, I just feel like that's a good teammate and that way you don't do that, it's doing it for you and then you figure out a way to automate that and it's even.
Speaker B: That's what I've learned from this. This, this team at one point is like it's the proper way to look at. This is one a series of jobs to be done and then that, that job to be done. Um, there's going to be need ah to be a deterministic component. So something that like the non negotiables that this just needs to be done right at this time every time. Like there's not a lot of variance. This just needs to be done. So at the uh, to get a good proposal built, it needs to look it needs to do these three things the same way every time automatically and then.
Speaker A: Okay, automatically.
Speaker B: Yeah.
Speaker A: Dude, I love that. Did you coin that or did you steal that? I love it.
Speaker B: I don't know if I can uh, coin that but uh, I don't know
Speaker A: where that came from but I love it. Okay, so keep mine.
Speaker B: Um, but you also need to be able, then it needs to pass to. There needs to be a little bit of judgment involved there. Right. And so it goes from deterministic, the probabilistic side of the brain. Uh, AI needs to kick in and be able to say, okay, we've got this quote back. Like, let's do the coverage comparison. Because that's not deterministic. Hasn't been great at that. Right. But now we have probabilistic AI. It's great at that. And then so even within the jobs to be done, there's still room for old school software. It's not going away. It's the stuff that needs to be done every time. And then apply the generative AI to within specific rules to get that part of the job done. And so it's stitching all this stuff together. Um, that's how you're able to have a teammate in the background doing stuff that you can trust. Right. Um, so I've just, I've just learned a lot from this team and it's like, it's a little eye opening.
Speaker A: Yeah. And you. One of the things that clunky, ah, transition. But I think it needs to happen is one of the things that I do love about one fort. Um, and I can say this proudly because, uh, a. Even before you guys became a sponsor, I was a huge fan. And when I first met Toby and heard what he was doing and saw it and shout out to Casey Nelson for introducing me, I was just like, dude. Because he was like, you got to come meet this guy. And so I went all the way to Texas just to meet Toby. And I was like, oh my gosh, this is amazing because, you know, one of the old, uh, school, as you said, old school technology, so to speak, that we all continue to use and will use until somebody comes up. Something better is email. You know, we all, whether you're csr, a producer, whatever, you're going to have email. And that's a source of contention for people because inbox is always full. There's always something falls through the cracks, whatever. But. And at that point when I met Toby, I hadn't heard of any AI that without having like its own like reactive platform of like, you have to type in this, you have to do this. And Toby's like, no, we just, we go through your email. It's like what? He's like, yeah, we're reading through the emails at all times and we're gonna be able to pull up, you know, all the emails from, you know, you to um, such and such client and be able to find the this or that. If they sent you an updated deck sheet or they updated a driver list, if they, it's all there. And then we just pull from that and it's all right there and done and we just connect to your systems and we do this. And my mind was melted after meeting him the first time. And so I can understand why it was an attractive place for you to go land, uh, next. But for the audience is just out here for the first time and their brain is now melted and they've had to stop the treadmill or they've had to pull over the car. Uh, explain what I, what I mean by that. You know, working through the emails, being proactive and you know, being able to provide a service for commercial insurance agents. If you're personal lines, keep listening. If you're commercial, pull the car over, stop the treadmill. Let's just, uh, lean in here a minute.
Speaker B: Yeah. So those of you that are, you've now pulled over your car, you're off the treadmill. Um, the thing that kind of hooked me, um, was I actually went to their, uh, office in New York and spent the day with them. And then I saw that based on an agency's email being connected, that their whole commercial book was mapped like their whole commercial book. So for one account we could see three years of policy information and all that means on the account. And you want to kind of open your eyes to how much back and forth there is in an account, have all of the email data compiled for one account. And then you like just filter and put your blinders on for that account. And it's underwriter back and forth, it's deck pages coming in. It's all of it, right? And um, so like, oh, this is pretty good source of truth here. Not really sure what you could do with all this, but then I learned that that was the jumping off point. And one fork can then take a look at last year's policy if it's a renewal and it can go and look and see like, okay, look at public data. Is there a third location that we didn't have accounted for last year? Okay, they're growing, so we need to actually, uh, get more information. And then it can compile and cross reference third party data to be sure. And then because it maps your whole commercial book, it knows that for this type of account, these five markets are in play for you. And then so it's like, hey, Heath, like, we think RAI thinks that these five markets should be approached with this risk. You could say this is where a human can be in the loop, right? You can say yes and market softening. So this sixth one is in play, right?
Speaker A: Yeah.
Speaker B: And, uh, so, um, then it, then it develops a checklist for itself. This risk needs these accords. The, the supplemental needs loss runs. Can't find loss runs. So we'll flag that. Um, and then. So all those eight things that would pile up as a to do list in the email. Now that account manager just has one task. It's just attach the lost runs that it couldn't find. Right. Um, and then it's a waiting game. Right? The AI is waiting for the quote to come back and vigilantly looking instead of your account manager. Um, and quote A comes back. All right, we'll start building the proposal. Quote B comes back. All right, we'll add to the proposal and then also do a coverage comparison and a compare and contrast. And it's like it's this living, breathing, deliverable that comes back in your email. So instead of a to do list showing up in your email, it's jobs are getting done from your email, which is pretty cool. And then you have this proposal that you can either put your particular seasoning on and fire off, or it can just go off to the prospect. So renewal administrative lift just shrank by 80%.
Speaker A: Oh my gosh. Again, why my mind was melted because that's unbelievable to me. And again, going back to this framework of a digital teammate, that's like the ultimate digital teammate that's reading through, combing through your emails and finding all that data and that information. Now let me ask you this, uh, for those that are might be skeptical, like, I don't know if I want AI reading all of my emails. What if I have an email that comes through from my wife that's, you know, pissed off at me about something or come through from my brother who's planning his wedding or whatever. Is it reading through all of the emails and is there some sort of security things there or is there any issues there? Have you had any feedback or pushback on that at all? Yeah, if we can edit this, we have to.
Speaker B: Somebody smarter than me is, um, in charge of our security and that's, that's a good thing. So, uh, our chief security officer was the first engineers at AT Coalition. So like, and we have all of our, we have all the key badges, right?
Speaker A: So the Soc 2 and Sock 2,
Speaker B: HIPAA and all that.
Speaker A: So yeah, I knew that. I saw that on your website.
Speaker B: And we Also, um, the AI is, we have very specific contracts with OpenAI and Claude, we are using the best model, depending on what is required, but we have private instances. So nothing is being stored or trained. Um, as far as the larger model. Right. It's very much just your agency. And then we are not storing anything that is not only not, not insurance related, we're not even personalized stuff. It's being parsed out. It's only reading and attaching stuff. It's small enough with a specific account. A commercial account.
Speaker A: Yeah. That's awesome.
Speaker B: And then if we do find that your wife's mad at you, it can tee up couples therapy and we can
Speaker A: get out ahead of that or order some flowers and send them to my wife's office. That'd be fantastic.
Speaker B: You know why?
Speaker A: You know, so you know what I did? That's hilarious. Um, no, that's fantastic. But no, I, I just wondered. So on that same note, um, me carefully ask this. I don't lose a sponsorship right now on this call. Um, but don't want to do that. What are some of the biggest pushbacks that people might have had with one for it so far? Is there any. Um, or maybe there was a challenge you guys solved from the very beginning. Maybe someone came to you and was like, hey, could we do this? And maybe you guys solved that challenge.
Speaker B: The, I'd say the active, the active challenge that we're working through right now and well, I would say implementing feedback right now is, Is the um, humans need the ability to apply their 20% or apply their seasoning to the proposal and there's still a lot of what AI can't do. Well, um, and I don't think it'll ever do it as well as the producer on the account is, um, is apply the judgment, the relevance judgment. Right. Um, the AI is picking up on third part, third party data, first party data. It's, it's, it's picking up on historical data on the account stuff from the email. It's picking up. It's great at connecting context. But I think what we're continuing to build out into the proposals and getting better and better at doing it is, is allowing the, the account staff to still say, well like the stuff that AI can't know or like they, they might have walked the property, you know, um, that's good three weeks ago and, and the, you know, the advocating for the account on behalf of the account like that, that's ultimately, that's what we're still trying to enable. That still needs to happen. We just, that's last mile stuff uh, we need to do the 80%, that's first mile and take slow skill. So, but it. Historically, our proposals haven't been incredible at allowing for that, and we're getting better and better at building that in and tweaking that. So that's, that's been fair feedback.
Speaker A: But I think to your point, what you brought up is, is good. And like, just because you have one for it or any AI tool but one for this matter, it shouldn't be, you know, like, trust, like it's your 100, like you just pushed the go, but you got to at least have that human in the loop, check it over, look over again, it's the 80%. There's still maybe that 20%. And that's any tool you use. And so I think that's just a good cautionary tale just to be able to say, hey, let's not just completely. Again, you wouldn't hope people don't put in some AI prompt, copy, paste, and stick it straight into an email without looking over it, because you never know. And I'm sure people do. But, um. And you brought up another good point of like, I, um, remember. And again, it hadn't been too long ago, you know, six or seven years ago when I was a commercial producer, it was like a big challenge that I would have, you know, with all my clients, not all of them, but several of my clients would be like, underwriter would come back to me and say, hey, you said they didn't do this. Their website shows they do. I wrote a lot of general contractors and they'd be like, you said, they didn't do roofing. They've got on their website pictures, uh, of roofers all over. They do. They do roofing or they not. So 14 would be a great tool to be able to tell that, hey, website shows they do this class of business. You don't have that class code listed correct.
Speaker B: Man, it's. That's so important to, to and sequencing matters. You want to, you want to approach that with the client and the prospect before it gets to the underwriter. Right. And so, um, yeah, there's a. There are, There are two doors to the one Fort Land, and that's email is one of them.
Speaker A: Yeah.
Speaker B: But that's really powerful if the account already exists. Right. And so like, new business, um, we have what's called a storefront.
Speaker A: Yeah.
Speaker B: And so that's dynamic, um, forms, um, that actually take their information and you can do a reality check. Right. And it's looking at, I mentioned first party or like um, public records.
Speaker A: Right.
Speaker B: Public data. So it will check. Um, website is one of the first things because, yeah, it's historically been a pain in the butt for producers. Like, oh, we, it's on our website, but we stopped doing that three years ago or we don't do that anymore. Or like we were, we were testing it and we wanted to see if like we could get roofing clients. But we don't really do roofing clients. Well, like, you know, like. Well, an underwriter is going to assume that you do roofing. Right. So it. And, and so if they check that, check no. And the website says yes. Like we're allowing folks to get ahead of that before it gets to underwriter desks, which is, which has been pretty huge. Yeah.
Speaker A: Yeah. I, um, again, I think there's so many use cases for that. You know, one for beyond what people are probably thinking of.
Speaker B: I'll give you another like, uh, act thing or feedback that we were actively implementing. We might, we might look like we got it all figured out, but any company like ours, like trying to do anything ambitious, it's like a series of things that we nail and a series of pieces of feedback that we're implementing, uh, if we're smart. And so, uh, a thing that we're working through is we have this storefront. Right. And so now we're letting agencies create like a Spotify playlist of coverages and make and like of.
Speaker A: Oh, that's cool.
Speaker B: And so, and it'll. That'll be built for that and make them so like that's their agency standard. And then make them deselect, unselect, you know, if they don't want it.
Speaker A: That's really cool. If I were to, um, Family feud style, survey 100 of your customers and say, what's the number one use case that you. Or the number one time save or whatever the question might be that you've gotten since you've been using one fort. What would be the top answer on that?
Speaker B: I think small commercial renewals.
Speaker A: Okay. Right. Um, because every time you touch those, you lose money. So if you could find a way to get less touches, that makes sense. Okay.
Speaker B: Yeah. Yeah. So survey says number two answer, um, is always, um, Accords. Yeah. Um, not happen to. To do, um, manual cords anymore, especially for ens. Right. That's where we like really excel. Um, we're awesome in states that have a high ENS burden. Right.
Speaker A: Yeah.
Speaker B: And it's like, you know, it's going to go ens, but you still have to go get your three declinations in most states and we got to go through this or we've got a form that we're doing that's like little, you know, we've got our way around it. So like it's either, it's either workaround or really high cost checking boxes and, and all roads lead to time intensive accords and supplementals being filled out and then going out to. Sometimes you have to do that for, for multiple brokers or MGA's or whatever. So like if we, we can just kind of one shot that for, for every account that's it's been really big for ENS accounts.
Speaker A: Dude, that's huge. Okay, so we, we've covered quite a bit of ground here. Um, I feel like we, we might be able to start closing up a little bit and you know. Uh, um. Yeah, but I appreciate you joining us, coming to hang out. Um, talk to the audience a little bit about you know, how easy it is to just start working with you guys and what that looks is people are thinking right now pricing model, this could be too expensive. This is going to be crazy. Um, tell them about this because I know but I want them to know just how easy you're going to make it for them.
Speaker B: Yeah, I just, I, I give everybody my Venmo and we work something out, you know.
Speaker A: Right. Okay. Uh, after that.
Speaker B: Yeah, after that. Um, well we've simplified it one we don't tax per user. We know that adoption is tough. So one thing that can block something is like a per user taxi. So we don't do that. It's a flat rate for an agency and it's based on commercial gwp. So, so we're priced to grow with you as you grow. Um, we don't want to charge a ah, million dollar premium agency the same as uh, $10 million agency, uh and vice versa. So it's like value based pricing. Uh, you should be closing enough deals. Um and it's um, really, I mean it's really easy to onboard. It's just we're trying to. As um, soon as you plug in your email I think minds kind of get blown when you see the accounts, commercial accounts and getting mapped and, and all the, the carriers getting mapped and all that. So what does a lot of the heavy lifting and then Anthony uh, does the rest.
Speaker A: What about contract wise? Is there some contract I'm stuck in for 10 years or um, stuck in a contract for what? What does that look like?
Speaker B: Um, it's, it's month to month pricing. Um, I think there's A. I think we've even done with the year terms of service, uh, or contract. So it's just not only is it on us to keep the agency on board through delivering, um, I think it's still a 30 day from being onboarded. It's a 30 day, no questions asked. I just don't like Caleb giving my money m back guarantee.
Speaker A: Right.
Speaker B: Uh, we totally de risk it that way. Yeah.
Speaker A: Awesome. Well, thank you. Um, I know there's some of those questions people ask as far as pricing goes, but I appreciate you sharing that. And, um, again, thank you for hanging out in the show today again with me. Thank you for being here. I feel like we're probably going to continue this conversation off air after this, but thank you for being here today. If the audience listening wanted to connect with you, what's the best way? Oh, besides, uh, your Venmo account.
Speaker B: Dang it. Uh, killing that grift. Uh, ah, text me. Um, I can even put my, my cell in the show notes if you want. Email, um, me, Caleb@ofort AI. Calebonefort AI. Find me on LinkedIn, send me a DM. Um, go on the website if you. If you want to look at it, just ask for a demo. I usually show up on demos too, so you can't. Can't get away from me. Um, yeah.
Speaker A: Thank you again. Appreciate that. Ladies, gentlemen, thank you for being here as well. And I'll, uh, see you in the next one.
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