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Transcript

Ben Markland: Welcome to the Insurance Leadership Podcast, where we talk about what matters now and how leaders can navigate change with clarity and confidence. I'm your host, Ben Markland, and today we have a timely conversation. Our guest today is Nicole Farley and she has a lot of insight into how data AI and technology is being used in her company and in our industry to kind of mold what they're delivering to customers and how they're working with carriers.

She's with Bold Penguin. Her previous title was Senior Vice President of Agency Carrier Operations, and she's more recently been promoted to Chief Insurance Officer. So she's, top of the totem pole there. And we appreciate you joining us, Nicole. I'd like you for starting out, let's just tell me a little bit about Bold Penguin. Tell me what you guys do, and actually I'm curious of the name itself. Where did Bold Penguin come from? What does that mean something? Is it just catchy name? Tell us a little bit about your company.

Nicole Farley: Bold Penguin. I'll start with the name. It's a great name for marketing. We've got the best swag because who doesn't love a cuddly penguin?

Ben Markland: That's right.

Nicole Farley: But the name actually came from that docuseries. I'm gonna blank on the name now, but the document about penguins, and there's a point in it where the penguin jumps off the iceberg into the water and the first penguin that jumps in is known as the Bold penguin. And so when our founder, Ilio was thinking of a name doing the research of what names exist out there. That kind of caught his eye as we're gonna be the front drum jumper of technology and get ahead of everybody. And that's where the name came from and how Bold Penguin came to be. The company itself, we are a kind of a premier platform for commercial insurance. We utilize technology data AI to elevate distribution, both for carriers and for our agency partners.

Ben Markland: Fantastic. Yeah I think I remember that documentary. That was a pretty cool one. Penguins are funny things. It's really interesting. Nicole, tell us a little bit about you. I know you're also a published author, amongst many other things so for those who don't know you, can you tell us a little bit about your background? What led you to your position today with Bold Penguin?

Nicole Farley: Like most people, I feel like I landed in insurance randomly. I was dead set on being an attorney. Went to law school. It was gonna be just like law and order do criminal law did not feel like law and order. So it was definitely not the path I thought it was going to be. And I was coaching hockey at the time in Chicago and the head hockey coach on my team was actually the CEO of Insureon and he goes, Hey, we need a general counsel. Do you wanna come over? And I was like, that sounds great, general counsel work's gotta be a little more fun right now than what I was doing. Knew nothing about insurance, didn't know what a bop was, didn't know any business terms, but I knew legal, so I joined Insureon as general counsel and over time started learning more about the business. Had a notebook full of words every day that I had to go home and Google, but learn more about insurance, more about kind of technology and gAIn more and more insight into what we needed to do to help agents. So transitioned my role there into more broker facing, carrier facing, building our relationships. And then eventually landed at Bold Penguin when they purchased Insureon back in 2022. And done the same thing over at Bold Penguin, growing out, our carrier relationships, our broker relationships, and most recently up getting our wholesale operation up and running.

Ben Markland: That's fantastic so I know that you guys look at Bold Penguin as a technology company and we actually say that a lot here too, we say we're a technology company that does insurance, right? So tell me kind of some of your technology initiatives. Tell me what it is that Bold Penguin does that would set you apart from some of the other competitors in your space. I think 

Nicole Farley: the most unique thing about Bold Penguin is that we look at it as tech and distribution. So we're gonna lean in heavily with data and AI to make the most seamless process we can, as simple for the end user to get to where they need to go. Our dream state, and I always say this to all my employees, is every risk that comes through the door, we need a home for it and we need to use the to get their. Using data and AI to find that best home is where we're striving to go. On the flip side of that, we also have a really good distribution pipeline through some of our partnerships, through our own internal wholesaler. So we get to see that distribution side. We get to see what the risks are looking like and as of recently, how much they're changing and what the needs are changing. Especially in commercial insurance, a lot more is going to the non-admitted market because of the global changes we're seeing in climate. More natural disasters. And so it's a really evolving marketplace right now. And so being able to see that on the distribution side and then build the technology to get ahead of that and support it and make it simpler is what sets Bold Penguin apart probably for most in this space.

Ben Markland: Yeah. Just so you know, a lot of our audience for the insurance leadership podcast we really have a lot more life and health agents, so I know you being on the commercial side. One of the parallels that I really see you mentioned data and AI a lot and I'm very interested in that data. I read something the other day compared it to one of the biggest commodities, almost like [00:05:00] oil. Data is something that needs to be collected. It needs to be refined. It can be traded, it can be sold to find its value, you've gotta analyze it. So tell me a little bit, I know you mentioned data quite a bit. On the commercial side what are some of the big use cases you guys are seeing for the data that you're collecting?

Nicole Farley: One of the most relevant, and probably not just commercial across the board is relevant, is being able to understand the submission you're getting in holistically. A lot of times we'll get forms. And a business has three different names across three different forms. And being able to understand as an agent, like what is ground truth? What is actually the name of the business, what is actually the what they do? Being able to pull data from third party sources, but also pull data from the forms and whatever submissions we get in and triangulate that to say, okay. Five different answers. What is actually the truth? And so that's how we're thinking about data is being able to pull it in from all sources is step one. But step two is actually triangulating it and saying, what is the [00:06:00] truth where, what do we need to do? And I think that's across insurance is becoming more and more relevant as, there's a lot of data out there, you don't know what's right, you don't know what's wrong. Customers don't know what to put 'cause it's phrased in a way that doesn't make sense. So we're really using data and our biggest use case is just being able to get to the truth of the matter quickly, easy, and without creating a burden on the customer.

Ben Markland: So let's go the other direction. So you mentioned AI as well, and that's something actually my last podcast guest we talked a lot about AI. We, here internally have started to pilot some AI in initiatives really on the kind of the customer service side and I know on the life and health side, a lot of people are hearing the terms AI agent and AI underwriting, and I think some people are embracing it. Some people fear it quite a bit because if you're an agent, what is an AI agent gonna do to me in my business? But then, on the flip side, things like AI underwriting we've seen, the turnaround time really shorten and [00:07:00] leaps and bounds and to your point, what you guys are doing is things being quick and things being correct are, that's what we can really use technology for. So give me a little view of what you're doing at Bold Penguin in regards to AI.

Nicole Farley: So from AI, same kind of fears, you're talking about agents saying, I don't wanna be replaced by technology. AI's coming in to take my job. We view it very differently. AI is there to help do the job that you probably don't wanna do. We wanna use technology to amplify agents. Agents are there to advise the consumers, they're there to give them the best coverage that they need. AI is there to help speed it along. And so that's how we're approaching it, is how can we use it to maybe compare policies to say why this one's superior. Can we use it to get to a result faster on quote. Things like that. We truly believe the agent's going nowhere. How do we just enhance their experience on the platform?

Ben Markland: Now, are you guys involved any on the claim side?

Nicole Farley: We are not today. So we stick really in the new business area a lot on policy compare. Especially when you get into those more complex, management financial lines. I don't even understand those clauses and I went to law school so, there is a lot to dig in there. So that's where we're investing time is how to pull those out and make it so a consumer can understand it, an agent can better explain it to an end consumer. 'Cause they get tricky in there. Lawyers like to put fancy words in things. And it's no different in insurance policies.

Ben Markland: I think it's funny when you talk to I'll use my mother as an example. She had a little fender bender last year and she went, and I don't even remember who her carrier was, but. A lot of these insurance carriers on auto policies, now you can take a picture of the damage and then you immediately get a dollar amount. And when I explained to her, she's I don't know what this AI is. I said, that's AI. There is, I don't and this is me assuming, but I can't believe there's somebody on the other end looking at a picture and coming up with a number. This is where, technology is starting to be used. And I told her, unfortunately, the truth of the matter is there's probably so much intelligence behind that, that it knows what number is the lowest possible number that you're gonna take versus going to a body shop and having to deal with all the quoting. So in, in a way, it's beneficial to the insurance carrier. It's making a process easier for the consumer and everything's out of everyone's hands a lot quicker. And that kind of, she's okay, I didn't realize I was dealing with artificial intelligence in that. And then I'll use another example, just me Christmas shopping for my children. You can't buy stuffed animal nowadays without some sort of tracking or data because they're gonna use it in a way to make it look like this is helping, better the experience for the child and I'm like, I'm not really sure why a teddy bear needs GPS and needs to know understand words and whatnot. Like I said, data is the commodity right now, and it's one of the most valuable products that's out there and everyone's out there trying to grasp kind of ways to use it to their advantage. I think it's great, [00:10:00] Bold Penguin has initiatives around that. A lot of the brokers we work with are dipping their toe in the shallow end right now, so that it's a conversation, I think we'll continue to have.

Nicole Farley: And I think, the generation coming up is. We don't wanna talk on phones. If I never have to pick up a phone, it's a great day. And which is funny 'cause I talk to people all day, if I want a virtual doctor's appointment, I wanna take pictures of my car versus having to take it in somewhere. And so it's just creating a better experience and meeting the end user where they want to be. And I think that has been the best part of AI is just making it just so much simpler as lives get busier as Christmas shopping takes hold, like I don't have time to go sit and have somebody take pictures of my car. It is a great experience for the consumer.

Ben Markland: Now you work with a lot of agents as well. Do you feel that they're prepared and embracing these changes?

Nicole Farley: I think it's, they're getting there. I think we hit this full, like AI and agent were the words of the conferences this year, every conference I went to had those two words plastered everywhere. And I think agents are curious, but as with everything, they're hesitant. Is it gonna replace them? Is it gonna do as good a job as them? And the answer's no. But it's how do we position that to be an asset? So I think over the next two years, what we're gonna see is AI shifting to being, to showing how it can amplify experience, versus just all these things coming out it's like, how do we now tallor that to make agents feel comfortable, to make consumers feel comfortable too? Some consumers are like, I don't like people touching my stuff. I don't like that they know where I live. How do we reposition it to not be this scary thing for users and plug it into workflows versus it just being like, Hey, check GPTs over here on the side go ask it some questions.

Ben Markland: Yeah, it's funny because, we work with tens of thousands of agents and, we have to keep a fax line open for the old guys because that's just, there's some of 'em that just aren't gonna change. I think that may be the demographic that is looking at this more fearfully because, hey, look I've got my groups, I've got my clients. I take them to dinner, I play golf with the owner of the company. But if some young hotshot comes in here and they gimme a quote that's, AI underwritten, I might be in trouble. So because what does it all boil down to, it's simplicity and then ultimately price too. And if someone can deliver on both of those, it's gonna be really tough to keep your old golf buddy out there.

Nicole Farley: I think it's interesting. I was actually listening to one of a podcast you guys did. They were talking about moving their agency down to the next generation, and I think one place that we haven't seen AI come in too much yet, but I think is gonna be a great ground for that, is training the next generation. Companies are hit or miss if they're return to office or not. How do we focus in on training people without being in an office? How do we work on training 'em in the ways we like to work? If they're not sitting next to me, listening to my phone calls, and I think AI is gonna become a big part of that, is training that next generation to have the same insurance knowledge at a faster pace. And being able to, hand off the business to mantain the relationships or bring in and staff up faster using AI versus the traditional sitting in a classroom, having a lecture [00:13:00] person to talk to you about insurance.

Ben Markland: Okay, so this is the insurance leadership podcast. So let's pivot a little bit from insurance and let's talk a little bit more about leadership. And I wanna talk about you specifically Nicole. So tell us, a little bit about your journey. Do you have any experiences that have molded your leadership style?

Nicole Farley: I think the earliest of that was truly the coaches I had across my hockey career. I was fortunate enough to play hockey through college, and I had some really good coaches that showed various levels of leadership style. It drained in my head like. What a team is meant to be. How do you talk to people? How do you talk to different types of people on the team? And that was a really good introduction into leadership. And then as I went through my professional career, I was fortunate enough to have some really good mentors and some really good leaders that gave me those things of what works well, how to look at it, and how to almost take a step back and find, to make sure you're not hiring a copy and paste version of yourself. Make sure you're bringing in the diversity of thought, the diversity of skill sets to your team to help create a rounded experience and be successful in what you're doing. And so I think between the two, between coaches I've had in my life and then the fortunate of mentors and leaders, I've been able to learn a little bit about how to have a very diverse, so the team and how to talk to each one differently and what motivates them.

Ben Markland: That's great, yeah I didn't know I was talking to a hockey star, so that's fantastic.

Nicole Farley: I live in North Dakota, there's not much else to do. I was born on skates and I spend a lot of time now with my kids on skates.

Ben Markland: Yeah, that's great. So we're in Mississippi, so not much hockey, actually not any, but I do remember when I was in high school, we had a kind of minor league team that I don't know how they did it, they froze the floor at the Coliseum, a couple weekends a month, and we loved it, but no one had any clue what they were doing, including the players I think half of 'em didn't really skate well, they just went out there and beat each other up but of course we loved it so it was.

Nicole Farley: That's half a hockey, so it's.

Ben Markland: It was fantastic. But that's really interesting. Another little niche that you guys do that intrigues me is ENS insurance. And that's for the audience that's not familiar with commercial insurance, that stands for excess and surplus. That's the risk that most carriers don't really like to deal with. And it seems like that's something bold Penguin does a lot with, so tell me a little bit about what you guys are doing with ENS.

Nicole Farley: In the commercial space. ENS used to be, I would say, like 10% of the risk you would see coming through at an agency. With the shift in climate, with the shift in some regulation, we're now seeing 30 to 40% of risks that come through actually land in the ENS space. And so what has historically been a very manual process, we have found an area that said, Hey, let's go and find a way to use technology, you as an AI to automate this. And so through our own wholesaler that we have at Bold Penguin, we're working with ENS carriers to digitize their quoting process, to be able to create a very digital payment and compliance workflow and really make it feel more like the admitted [00:16:00] space. And so 2025, and as we go into 2026, we're continuing to look at how do we create a better experience in that space? Because with everything going on, we don't think that's going away. More and more carriers are being selective with what they wanna write. They're watching their profit lines very closely. And so we see more and more moving into that ENS space, and we wanna create that digital experience there. That's been built over the last, 10 years in the admitted space.

Ben Markland: Just outta curiosity, is there anything really bizarre that you've seen that you guys got successfully insured?

Nicole Farley: No, I've seen some weird ones. I will say most of 'em are around the coast. My favorite ones to look at are restaurants open flames. I'm like, people think that's a good idea. Apparently churches who wanna take their congregations to do cookouts, for people. There's just weird things that layer in and out of what would seem normal admitted risks and you're like, oh, that little tweak there puts you into this. That decision to go rock climbing probably moves you into the space.

Ben Markland: Alright, Nicole, in regards to data, I know we've talked a lot about data and the importance and just the complexity and the size of data. From your view, what's the next big step for data-driven decision making in our industry?

Nicole Farley: The next step you're gonna see is how to skip the application process altogether. We've been looking and talking about that a lot as we look over the next three years of development in our company and we see the world of just going to chat GPT, going into Google and no longer having to answer those questions, like a form, being able to come in, know who that user is, and just get a quote on the glass right then and there. So we think that's the next journey is the expiation on the new business side of quoting and then creating a very curated panel on the backend from a carrier perspective to solve for that specific risk.

Ben Markland: Yeah, I think that's great. I think, applications are always a bottleneck. And lots of situations and the legalese that exists on them, you're right. I know you alluded to earlier that your average consumer, small business owner, you give them a 10 15 page application for group insurance and they don't stand a chance, which is why our agents are important. But then again, some of them don't stand a chance either, right? A lot of these things haven't changed probably since before I even began in this industry. So I agree with you, I think, AI and big data could be something that could really potentially eliminate that process and really, let's be honest, everyone wants it to go away or at least get easier.

Nicole Farley: I agree, on a commercial standpoint. Classification has always been our hardest thing. You know you have that guy who mows lawns, but one month out of the year he shovels snow. That creates a completely different risk. And how do you get that information out of him? He's probably not thinking about that when he's oh, I need, I have a landscaping business, I mow lawns that's all I need to think about. But it's like that one time he shoveled snow. And so how do you get that out of somebody? And a form is not a great way for that. It feels very sterile. So having a more conversational way to get that information [00:19:00] to provide a quote. That's where we want to go.

Ben Markland: We've talked a lot about AI as well. Obviously, we've talked about some of the applications of it, but I think on the other side, there's a point where there needs to be guardrails with AI. What do you think are some important guardrails to be in place in order to really properly push that out or use that within your company?

Nicole Farley: Number one is transparency. Being able to let somebody know AI is being used. Secondly, where it is being used is very important. You see it today, ads on Facebook, things pop up on Instagram, and it's was that real? And there's no notion like, Hey, that's actually AI. So giving the consumer, giving the agent knowledge like this is AI, this is where it's being used, is the most important guard I think we need to put in place. And then when you get that output of it, making sure it's known to AI was a part of this output, so that if there's something that comes back, we know where it came from. And it's not sitting there being like, oh, a consumer said this, the agent said this. AI has to be a part of it, [00:20:00] which is great, but there has to be notification, there has to be clear audit trails to come back, in downstream claims and downstream lawsuits even. You need to be able to point to where AI was used and how AI was generated to do that. So to me, like number one, guardrail is the notification. And I think the second is just using it in a limited way. We go out and use AI for everything. AI is just gonna take over and do what kind of the only model does. Human intervention is huge, human in the loop is huge. And so being able to make sure a human always has oversight is going to be important I think for AI in the future.

Ben Markland: So with your law background, you do you envision there being lawsuits around AI or are you aware of anything in your industry that's already happened?

Nicole Farley: I'm not aware of any right now. I'll say, and then when I talk to our engineering staff, I always have like my legal brains coming out. I apologize, but, I just, I foresee it coming. You see it already in media, in the media industry. Movie stars have come out and said, Hey, look, we need these in our contracts.We need to protect our image. The same thing I think can happen in other industries. So getting ahead of that and seeing and taking from what we see in other industries and bringing it into ours and getting ahead of that, I think is gonna be crucial.

Ben Markland: I agree, and actually it's, the reason I mentioned that I actually host another webinar with a lawyer that's a partner with an association that we work with and he's always diving into the HR side of things. So he does a webinar that is generally geared towards small businesses so their HR people can be, kind of in the know of what's going on, what might affect them and he did one about a month ago, specifically around AI and lawsuits, and I was trying to rack my brain, you're right, AI, eventually, there's gotta be copyright stuff that's gonna happen because AI can write a book, they can sing a song, they can make a movie, but how would this affect small businesses? And he used an example there was a discrimination lawsuit. And it wasn't a small business, actually a very large business, I'm not gonna name. But they were using AI to screen resumes for job applicants. And it was for an executive level position. And what happened was AI uses the information that's given to it, right? And it noticed that there were no women in executive positions at this company therefore, they threw all the women out of the resume. There's something that, AI will get better, but then again, that's something a human wouldn't have done. And you have an HR person that's hitting the easy button saying, Hey, I got a thousand applications. Let's throw it through AI. And guess what? Now you got a lawsuit for discrimination because you threw all the women out so, that's something I think there's still gonna be some knobs to have to dial in AI. And I think lawyers are probably gonna have a little heyday on it at some point, but.

Nicole Farley: Oh yes. I feel like it's the new TCPA coming I think lawyers have gone heavy on that. AI is the new frontier for them when they get into it.

Ben Markland: Yeah. Hey, we're all gonna learn together and we'll see how it all works out. Nicole, I appreciate you joining us. I appreciate your insight, your knowledge on the subject matter. You're one of the first that we've had from a commercial background very new to us and our audience. I think it's very interesting. I appreciate the conversation. So thanks for joining us today.

Nicole Farley: This is, a great conversation to have and it's good to see that some of these common threads are across all of the insurance industry and not just a commercial problem or just a life and health problem, so it was a really great conversation.

Ben Markland: To our listeners, thanks for joining us today. I hope everyone enjoyed the conversation. We'll see you next time. And remember, simple solutions, real results. That's great leadership.