The following interview is a conversation we had with Sivan Iram, CEO & Founder of Flow, on our podcast Category Visionaries. You can view the full episode here: $20.6M Raised to Transform Commercial Insurance Wholesaling with AI

Brett
Welcome to Category Visionaries, the show dedicated to exploring exciting visions for the future from the founders who are on the front lines building it. In each episode, we’ll speak with a visionary Founder who’s building a new category or reimagining an existing one. We’ll learn about the problem they solve, how their technology works, and unpack their vision for the future. I’m your host, Brett Stapper, CEO of Front Lines Media. Now let’s dive right into today’s episode. 

Brett
Hey everyone. And welcome back to Category Visionaries. Today we’re speaking with Sivan Iram, CEO and Founder of Flow, an AI Force commercial insurance wholesaler that’s raised 20.6 million in funding. Sivan, how are you? 

Sivan Iram
I’m doing great, thanks for having me. 

Brett
Super, super excited to have you here and really looking forward to this conversation. Let’s go ahead and jump right in. What does Flow do? 

Sivan Iram
Like you said in the intro, we are an AI first commercial insurance wholesaler. That means we help retail brokers and agents find commercial products for their clients. We have different approach at it. We’re, we’re not, you know, labor intensive and take forever to respond. We’re using AI technology to improve our internal operation, to elevate the level of service that we provide. Not only responsive, consistent and proactive, but also provide a level of insightfulness, recommendations, expertise that people would expect to get on very large enterprise account. We provided any size deal. Our specialty is small commercial and mid market accounts. As you know, they don’t get the love and affection of brokers because those deals are just not profitable. If you make 20%, you make 10% commission on those deals, you know, and it’s a $10,000 deal. 

Sivan Iram

You can’t really spend a lot of time on it if you’re a traditional player. For us it’s very different. We go through, you know, our workflows, we go through policy analysis and comparison. We’re able to place business with our carriers very quickly and allows us to really invest a lot in every size account and to really execute for our clients. The sweet spot for us right now we specialize in three lines of business, executive lines, so cyber management, liability, that includes dno, crime, fiduciary, EPLI and such, and professional liability, a lot of lawyers, insurance agents, medical malpractice, accountants, lawyers, and more. 

Brett
How did you decide on those three and then which did you begin with? Did you begin with all three or did you begin with one of those lines? 

Sivan Iram
We began with all three. We felt like when we started the brokerage, we saw that the market was starting to loosen up to soften up with those lines of business. Property still naturally, very hard. As a new wholesaler, it would be very hard to get capacity partners to commit in. Very hard to place lines where the market is really hard with property. For us, those lines of business are traditionally still very much so Flow through the wholesale channel even in a relatively softer market. And the main reason for that is those lines of business require expertise. Specialty lines, oftentimes retail brokers, retail agents rely on wholesalers not only for market access, but also for expertise, insights, advice. And we felt like that was the sweet spot for us. 

Sivan Iram
As I look into the future, for us to expand to more PNC lines is definitely going to be a big opportunity. 

Brett
When you think of sexy businesses, commercial insurance wholesaler probably doesn’t come to mind for most people. What made it sexy for you? Like, why’d you decide to go into this in the first place? 

Sivan Iram
Yeah, you know, I’ve built my career in what you would call boring businesses. I find passion in technology that moves the needle for businesses. The connection between technology and business was drawn to from early days. I started my career as a software engineer and I transitioned to business roles about 12 years ago. I spent the past decade focusing on digital transformation, the challenge of bringing innovation into what you would call boring industries. I’ve done a lot of work with supply chain companies and manufacturing, automotive and energy. And to me, to come in and face business challenges, the two that kind of to me are very complimentary and really exciting. On one side, the technological challenge of bringing innovation that is meant to fit with a legacy technology stack in itself is a really big challenge. 

Sivan Iram
And then the complimentary side, the yang to that yin is the human challenge with adopting change and innovation. How do we get through change management? How do we implement an innovation within an organization beyond a C suite decision? And those two kind of put me in the position about three and a half years ago where I wanted to start my own company. I found myself an insurance. Everybody insurance would tell you I found myself an insurance because of a family member that’s also in the space. I started to ask lots of questions, get connected with dozens of people. You ask questions, you find gaps, you connect the dots and you come up with a vision that people can really rally behind. That’s the entrepreneurial journey really to find those gaps, connect the dots. 

Sivan Iram
And to me, the wholesale space was really exciting and interesting because one side I saw an intermediary that everybody agreed plays a paramount role in the value chain. But I also saw people complain on the lack of responsiveness, the poor service they were getting, specifically in the segment of small commercial mid market accounts where brokers just can make a lot of money. And to me the inspiration was how can we leverage technology to bring the same enterprise grade service to this middle market and small commercial space. So I’m passionate about technology and business and how business can use technology to innovate, to disrupt. And I find I’ve definitely changed my mind about insurance. I tell you, one of the most kind of inspirational slash humbling journeys I’ve went through is I was looking at the industry from the outside. 

Sivan Iram
In not knowing a lot about it, I held a kind of a very. My perspective was influenced by my experience as a consumer coming into the space, learning about first and foremost how important this industry is to as the foundation for entrepreneurial endeavors. Without risk transfers, business owners would not start businesses. There’s no doubt in my mind if as a business owner you were liable to your workers getting hurt and to get sued because you know you made a mistake, you know, having a workers compensation claim or a cybersecurity breach. If were liable as business owners, regardless of whether you’re a startup or not, every single risk that you could face, nobody could pay the claim because every business, you know, one point or another faces the claim. 

Sivan Iram
The fact that you can transfer risk to a company and pay them premiums for that to me is really the foundation of our economy in a big way. And that was a really key learning and appreciation of the industry and then how smart and devoted the people within the industry are. You know, not only our own folks, but I meet people every day from all over the value chain. I get inspired by the stories they tell me of how they help somebody get coverage and it saved their business, or horror stories and things that happened and the industry was there for them. So definitely changed my mind and I love every second of it. 

Brett
You know, through my agency I’ve been running for the last 10 years, I’ve worked with 500 companies every industry can imagine. And early on I had that idea that like there’s some industries that are just boring. I found that, you know, complete bullshit. Every industry I’ve worked in is interesting. As soon as you start to dig in, even if face value it looks boring, everything’s interesting. I think if you’re an entrepreneur, you start digging in, learning facts, you meeting the people, everything can be fun. And I’m sure insurance is the exact Same thing, absolutely. 

Sivan Iram
And I think that’s a message that we need to tell young folks more. I think that people often go after what’s sexy and what’s up in the news, and I think they get carried away after Fool’s gold in that regard. I was like that when I went to school and I told you I’m a software engineer. My program specialized in telecommunication systems because it was back in 2008 and, you know, telecom was all the rage. And I went into that industry as a young software engineer, and I found that specifically wasn’t for me, the bigger question wasn’t necessarily the industry and what it did. It was much more the company I was in and how did it aim to disrupt what was different about the technology? We wanted to build much more. So my immediate boss and mentor, did they believe in me? 

Sivan Iram
Did they want to build me up and teach me? Those things really matter. And like you say, I find that, you know, when you’re generally intellectually curious about things, you can find interest and passion in almost everything. It’s less about the greater industry. It’s much more about your position in IT and the strategies of the company you’re in, the technology you bring, specifically, if you’re a technology person, I think that message needs to be taught more to young people. You know, go less for the sexy and shiny, but go more for those kind of factors that I’ve highlighted. 

Brett
Forget being an astronaut going through insurance. That’s the message that gets here. 

Sivan Iram
Yeah, we’ll try different things and find your passion through it. Don’t think that it’s like, you know, on the flip side of it, I got two boys, and both of them are convinced they’re going to be soccer players. So we’ll wait and see. 

Brett
So three and a half years ago, you have this idea. You start building. How long did it take until you had your first paying customer? And then talk us through that process. How did you convince someone to give you money? 

Sivan Iram
That’s a great question. So the vision for the company Was to bring the level of enterprise service to smaller accounts and to do that through technology. The first concept that we wanted, the way that we wanted to execute that vision, is to build a platform where agents can log in and place business with wholesale markets. We took us about a year and a half to build the platform, to make appointments with carriers, and to go out and find agents who were willing to work with our product. And we did see revenue. We got paid for those early licenses. The vision was compelling and so were able to convince people to pay us the licensing fee. However, we found even though we had pockets of success, you could see that there was no brush fire. 

Sivan Iram
There was no product market fit moment where everything just, you know, works right and people just kind of calling you up, asking to join. The two key reasons for that, we found was, number one, change management is really hard. It was difficult for people to change their ways from moving from the inbox and emails and to log in. You know, they were working with a number of wholesalers they were using. Everybody has a platform today, carrier portals and platforms and whatnot. And we found that there’s a true concept of platform fatigue. You know, forgot my password, what’s my login credentials? That was one. But it wasn’t actually the biggest thing. 

Sivan Iram
The bigger issue was that they were looking to us as their wholesaler, not only to get connected with our markets, which they could on the platform, but they needed our expertise, they needed our guidance, they needed our advice and insights. And so we decided about a year ago to bring this platform in house and work with our agents in the way that they love to work with wholesalers, which is the email. Instead of carving out and saying this segment is not profitable, so we’ll set up a portal and move the burden of placement down to my clients. We realized that wasn’t the right approach. We take in submissions via email with attachments. And we employ technology to be really efficient with the way that we place. We structure that data with AI agents. 

Sivan Iram
The core technology for Flow is a system of AI agents that help our brokers every step of the way. From structuring the submission, recognizing what carriers have that in their appetite. So to do risk appetite matching place business in the right way. Sometimes it’s via APIs if the carriers have it. Sometimes it’s going to be with all traditional email. If the coverage is great or the quote can be really competitive, the market could be really competitive on pricing, but they don’t have an API. We definitely do not want to exclude them from the placement getting the quotes back, wrapping it with our insights and analysis, doing policy comparisons and sending out the proposal. We do all that with AI agents, but we always have a broker in the loop, we always have human supervision. 

Sivan Iram
And when we started to build, that immediately started to catch fire. In the past nine months, we’ve been tripling our top line every single month. We’ve been tripling our submission volume and we’ve been absolutely inspired by the excitement and the passion that our clients respond to our service. As soon as they send us the first submission immediately they recognize the difference in working with the old traditional, you know, big houses where they send out a request for a $5,000 account and they don’t hear for two weeks versus us, where they get the response in 15 minutes, they get the first quote in an hour. And typically they can bind, you know, within the day. So that’s a complete game changer for them, allows them to focus on. 

Sivan Iram
I always say this, you know, retail agents, they have 95% of their book is they just want to place this, I want to renew this book. I just, I don’t want to hear about it, I just want it done. And 5% is on fire. 5% is clients who need it yesterday. And there’s a gap and there’s a rich. Something about it is hairy. We want to rest their mind at ease on the 95% and help them solve through the fire drills that we all just have to go through. And that was the shift. And again, the past nine months have been absolutely inspirational for us. It has not been hard to convince people to give us their money because it’s a success fee, it’s a commission based dynamic. They continue to bind and we take our cut. 

Sivan Iram
And it’s been just absolutely inspiration to see the response from our clients. 

Brett
Something else you mentioned earlier in the conversation. So you said you have this SMB kind of mid market that wasn’t getting a lot of attention from the rest of the industry because the general belief was there’s no money or there’s limited money to be made there. As you were talking about this idea with the people in the industry, maybe investors, like, did anyone try to convince you not to do it? Like what I see a lot, at least in the SaaS world is like everyone wants to go enterprise, no one wants to go S and B mid market. Investors are always trying to convince companies go up market for you. What were those conversations like? 

Sivan Iram
Well, I think the notion of small commercial or mid market wasn’t a big challenge because I think people recognize the Gap. I think as I talk through the notion of mid market not getting love from existing players and through technology you can turn the unit economics to be profitable and take over the segment and also disruptive innovation. And you always start from the bottom of the market and you keep up before the incumbents know it. So that wasn’t the big challenge. I think early conversations with investors, the biggest pushback is like why aren’t people removing the wholesaler? Like what justifies their existence? I think a view, a very cynical traditional investor view was it sounds to be excessive. It sounds like waste. You don’t need two brokers on a deal like the retail and wholesaler. You know, we should do away with the wholesaler. 

Sivan Iram
And we said you cannot replace that. They bring a lot of value in the form of expertise and market access. They provide consolidation for the carriers. There’s a lot of value in it. I mean there’s a reason why the segment has absolutely exploded. It is true, it’s pretty consolidated from the number of big players that’s in it. Definitely more so than the retail side or the carrier side. But as the total market cap, the segment has absolutely exploded with the growth of amwinds and RT and CRC and Burn and all those folks. So really kind of convincing people that this, the segment is healthy, it’s growing ensuing as a space is growing extremely fast. You know, that was the bigger task. 

Sivan Iram
We’ve been very fortunate that our seed investors in Lightspeed are very experienced not only with traditional SaaS businesses, but InsurTech is a segment specifically. They have some big investments in the space. They understand the value chain. We did not have to convince them in the existence of a wholesaler. And they’ve been a phenomenal support of us since day one. 

Brett
Let’s talk a little bit about marketing. So I don’t know too much about the insurance industry, but I know there must be a lot of money in the space just from watching the Super Bowl. Every commercial is an insurance company with some, you know, a list actor kind of given the same pitch, doing the same types of that. My whole life I’ve been seeing these insurance ads, so I know there’s money in this space. How are you approaching marketing and you know, do you view it as you’re competing with any of these big companies that have what seems to be unlimited budgets to have, you know, Tom Cruise lever a list celebrities in their ads? 

Sivan Iram
Well, we, fortunately we don’t have to compete with them. Most of those folks sell you personal insurance. So the type of insurance that individuals would buy. 

Brett
Right. 

Sivan Iram
The guy calls estate farms, deliveries of the world, home, auto. That’s kind of the biggest chunks of personal insurance. In a complementary way, you would find medical benefits and medical insurance also to be a huge segment where you would see lots of commercial. That’s a consumer plague. Right? That’s why they appear on Sunday, you know, Monday night football and the super bowl and NBA games. For us, we focus on commercial insurance. So the type of insurance products that companies would buy, it can be for us, as I said, it’s cyber management, liability professional. But the space you can have workers compensation, commercial auto, property insurance, casualty lines of business like general liability and so on. So marketing is much more targeted. Right. 

Sivan Iram
I will say that when you see companies focus their marketing not on what they sell, but you know, they embellish with a listers to me that says that the product is a commodity. And it’s almost like that, you know, to see segments being a commodity. If there’s like a credit card that’s associated with it or like a club that you can join or a mileage for airlines is great. I mean, if I put you on a plane and I strip away the logo, you would know what airline that was. It’s a commodity product. So they try to put you as and give you miles to keep loyalty programs and whatnot. 

Sivan Iram
You know, if you pull up to a gas station and you fill your car and they strip it away from all the logos, you wouldn’t know if it’s shell or 76 or any one of the national or domestic lines. It’s a commodity. Gas is a commodity. That’s why we see those loyalty programs. Same goes for insurance in a big way. The personal lines, a lot of it is around it’s commodity product. So you bring in a listers trying to convince people to join. It’s effective. You know, it’s been working for them. Thankfully, we don’t need to struggle with it. I don’t know if we can pay an a list to market commercial insurance. 

Brett
I mean, you know, it’s effective because like off the top of my head I can like sing the songs of certain insurance companies for like no reason other than I’ve been seeing their ads forever and ever. Do you think that commercial insurance is going to become commoditized at some point? Like is it going to follow a similar trajectory and you’re going to have no choice but to get Tom Cruise to get your ads? Or is it going to be different? 

Sivan Iram
I’ll start by saying that I am jealous of Jake from Steak Farm. Like that guy, that actor, you know, getting to hang out with all those awesome people. Yeah, I want to do that. There are segments in our space that are slowly commoditizing. Those are the older products that are becoming very kind of antiquated. They’re still, you know, companies buy them left and right, but they’re very standardized. A good example would be general liability or BOP business owners. They’re very straightforward. I think the complex world of risk is still very hairy, still very nuanced, relies on expertise. But generally speaking, when we think of corporate marketing, account based marketing paradigms fit the mold better. We know what the universe of clients look like. We don’t need to use loudspeakers, we don’t need to use, you know, ads on the highway. 

Sivan Iram
We’re very targeted in our approach. We do social media, we do events. You know, hitting the pavement and meeting clients in their office is still a huge part of the business. And you know, using email lists, targeted clients. I still think that’s going to be the majority of marketing in commercial insurance going forward. 

Brett
Is there anything you’ve tried in marketing that just didn’t work? Something maybe you like thought would work like this should obviously work or for sure should work and then you tried and it didn’t. 

Sivan Iram
We experiment all the time. Let me think if I can come up with something that did not work by any means. Yeah, you know, we, I don’t think that it’s a failed exercise. We’ve not been able to do it successfully in the past and that is to do cold calls and cold emails. We, you know, got access to large lists of agencies, agents and agencies, try to reach out and kind of make the claim, to pitch the company to talk about the offering, to see how we can be valuable as a distribution partner. It has not worked. We tried twice, two separate, different ways. It did not work. I will say that we did. 

Sivan Iram
Recently we added a really smart, experienced marketing leader to our team and we’ve made a recent attempt two weeks ago with a pretty smaller list and we saw some really nice conversion numbers. So I’m starting to believe there’s a way to crack that nut. 

Brett
What do you think changed? We’re using different content. Was it Just more niche that was more specific. Like what led to this experiment being more successful, do you think? 

Sivan Iram
I think a few things changed. One thing that’s really important was that instead of coming in from a generic company email, we addressed it from our existing brokers and it is still very much a relationship driven business. And, you know, having it to the face of a person really does matter. I think we learned how to communicate our value in a more concise, articulated way. We found our voice in the past year again with kind of the changes to the go to market strategies that I mentioned before. We have a much crisper, clearer, better elevator pitch. Whether I meet you in the elevator or whether I send you a cold email, we see better conversion numbers because we can tell the story, we distilled the value better and we can communicate that. I think those factors together work really well. 

Sivan Iram
You know, the first two attempts, which happened two years ago and last year we got zero conversion from, you know, a large number of emails. This exercise last week, I think it was only a couple of hundreds of people and we already got already bound deals based on the replies, people started sending a submission. So again, I see a path to real value here. 

Brett
What else from a marketing perspective or a growth perspective, like what’s on the list for maybe 2025? Anything big coming up? 

Sivan Iram
Yeah, I mean, we’re continuing our investment in kind of the army of AI agents that help us execute better. At the end of the day, I’m a true believer that the power in our industry specifically for wholesalers, because we serve the retail broker, we serve the retail agent. The power lies with the frontline teams. When they have accounts that they need to serve, they need to ask themselves. There’s a mental decision making process where they say, do I take this directly to a market, to a carrier that I work with, or do I take this to a large wholesaler? My incumbent, you know, hardly ever responds or do I send it to Flow? 

Sivan Iram
And if we’re able to win that battle in their minds, because we provide responsive, consistent, smart, insightful service that would, you know, win us the next one and the next one. It’s just good service at the end of the day wins the business. So that’s what we focus most of our development efforts internally goes towards. How do we improve the retail broker experience? How can we be more proactive, more consistent, more insightful and so on. On the marketing and sales side, we’re still continuing to build our team in a big way. You know, we’re hiring in several Positions within our sales and marketing teams. People are curious, definitely, you know, check us out. I do not want to plug in, but I will say flowspecialty.com or our LinkedIn page also has our positions posted there. 

Sivan Iram
There’s a lot of going out to events and social media and we’re going to do, you know, webinars and trying to get to build loudspeakers to kind of send a message out and hope people respond well and give us a shot. The barrier to entry, the barrier to try us out is incredibly low. People just need to send us a submission and see the magic happen. We don’t need any appointments, we don’t need any agreement signed. We’ll do that after. Once we get a bindable quote where the client actually wants to bind, then we get through the red tape. But we try to show value as fast as we can and really lower the barrier to giving us a shot. 

Brett
You talked about a few questions ago about the message getting clear, the narrative getting a lot more tight. Was that like a specific kind of focus? Of like, okay, we’re going to do a workshop. We’re going to have these people in the team involved. We’re going to refine our messaging or is it more kind of incremental? Like you’re on runs thinking about it. You’re just thinking about it all day and like, then it kind of came out. 

Sivan Iram
Well, it’s a combination of both because you’re constantly out there and you’re constantly listening to what people tell you they need, what they tell you they love about what you do and what you need to do better when you’re constantly in the weeds with them, especially in an early stage, like we are. But then we also have this phenomenal internal person that we added to the team that brought a level of strategic view and the ability to use words to tell stories in a way that I’ve never seen before. And that helps us take all the knowledge that we’ve accumulated in the past year, servicing our clients and distilling it into a very clear message that people respond really well to. 

Brett
And final question for you before we wrap, let’s zoom out three to five years into the future. What’s the big picture vision look like? 

Sivan Iram
Yeah, we want Flow to be the largest wholesale broker in mid market, in the mid market segment. We want to bring that level of service and expertise. We want to help improve client outcomes at the end, get better coverage, better prices for our clients, for end clients. I think for us, the growth path goes through deepening our Foothold. With our existing lines of business expanding to more geographies and then also expanding on the lines of business that we support, expanding to property and casualty would be a natural step. You know, call it year three, year four. And building on that to just kind of increase or expand our foothold, work with more carriers to be able to provide more tailored solution for our clients. 

Sivan Iram
I think at a certain size, you can really be in a position to provide unique programs and unique solutions to your clients that they can get elsewhere. And I think that to us, the way that I see the vision for flow is, you know, if you ask me, how do I benchmark my work, how do I benchmark our company’s work? I would say through the lens of impact. We want to be a positive force in the wholesale space, in the insured commercial insurance space at large. I think we’re building technology that’s going to change the way that this industry does business. 

Sivan Iram
I think it’s going to free up people to focus more on what people should do and want to do, which is, you know, being creative, serving clients, negotiating, bringing a level of expertise that really make them be appreciated and appreciate their own work and being proud of and eliminate all the rudimentary work and waste that is just spent from data entry and all these archaic systems. And again, for us, I think it’s really going to impact the way the industry does business. 

Brett
Amazing. I love the vision. I don’t know if you know that meme that goes around online, but it’s, you know, if I win the lottery, I’m not going to tell anyone, but there will be signs. I think for you, that’s probably the super bowl ads that were talking about. You don’t have to tell me that you’re Super Bowl. Super bowl. Ten years from now, if I see a Flow advertisement. 

Sivan Iram
Well, no, exactly right. I think one day we might have Jack from Stage from working for Flow. 

Brett
Amazing. I love it. It’s been an awesome conversation. I’ve learned a ton. I know our audience is going to love it. So thanks so much for taking the time. 

Sivan Iram
Really enjoyed it. Thanks for having me. 

Brett
No problem. 

Brett
This episode of Category Visionaries is brought to you by Front Lines Media, Silicon Valley’s leading podcast production studio. If you’re a B2B Founder looking for help launching and growing your own podcast, visit frontlines.io Podcast and for the latest episode, search for Category Visionaries on your podcast platform of choice. Thanks for listening and we’ll catch you on the next episode.