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When most companies see an “unprofitable” market segment, they walk away. Flow saw an opportunity.

In a recent episode of Category Visionaries, Sivan Iram, CEO and Founder of Flow, shared how his AI-first commercial insurance wholesaler raised $20.6M by transforming how the industry serves small and mid-market accounts.

 

The Traditional Wholesaler’s Dilemma

Commercial insurance wholesaling has a math problem. As Sivan explains, “If you make 20%, you make 10% commission on those deals, you know, and it’s a $10,000 deal, you can’t really spend a lot of time on it if you’re a traditional player.”

This economic reality created a clear market divide: large accounts received white-glove service, while smaller accounts were often ignored or underserved.

 

A Failed First Attempt

Flow’s initial solution seemed logical: build a self-service platform where agents could handle smaller accounts themselves. The team spent 18 months developing the platform, secured carrier appointments, and found early paying customers.

But something was missing. “We did see revenue. We got paid for those early licenses,” Sivan recalls. “However, we found even though we had pockets of success, you could see that there was no brush fire. There was no product market fit moment.”

 

The Pivot That Changed Everything

Through customer feedback, Flow discovered two critical insights. First, there was significant “platform fatigue” in the industry. “Everybody has a platform today, carrier portals and platforms and whatnot,” Sivan notes.

But the bigger revelation was about value. “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.”

Instead of forcing customers to change their behavior, Flow made a radical pivot. They brought their platform in-house and met customers where they were – email.

 

The AI-Powered Breakthrough

Flow developed a system of AI agents to handle the labor-intensive parts of the process internally. “We structure that data with AI agents… from structuring the submission, recognizing what carriers have that in their appetite… wrapping it with our insights and analysis, doing policy comparisons and sending out the proposal,” Sivan explains.

The results were immediate. “In the past nine months, we’ve been tripling our top line every single month. We’ve been tripling our submission volume,” Sivan shares. What traditionally took weeks now happens in hours: “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.”

 

Growth Through Reduced Friction

Flow’s approach to growth deliberately removes traditional barriers to entry. “The barrier to try us out is incredibly low,” Sivan emphasizes. “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.”

This strategy focuses on winning what Sivan calls “the mental decision battle” – being the obvious choice when brokers decide how to place business.

 

The Future of Insurance Wholesaling

Flow’s vision extends beyond just serving underserved segments. They aim to become the largest wholesale broker in the mid-market segment by expanding geographically and into new lines of business.

But perhaps more importantly, they’re demonstrating how technology can transform traditional industries without disrupting established workflows. As Sivan puts it, “We want to be a positive force in the wholesale space… I think we’re building technology that’s going to change the way that this industry does business.”

For B2B founders, Flow’s journey offers a crucial lesson: sometimes the biggest opportunity isn’t in changing how an industry works, but in making existing workflows dramatically better through technology.

 

Actionable
Takeaways

Listen to how customers want to work:

Flow initially built a platform requiring users to log in, but discovered clients preferred email. Rather than forcing behavior change, they adapted their solution to work within existing workflows while adding AI-powered efficiency behind the scenes.

Focus on underserved segments:

By targeting small and mid-market accounts that traditional wholesalers found unprofitable, Flow created a compelling value proposition. Their AI-driven approach made these segments economically viable while delivering superior service.

Product-market fit requires deep industry understanding:

Despite having a working product and paying customers, Flow didn't achieve true product-market fit until they understood the fundamental role of expertise and guidance in wholesale insurance.

Cold outreach can work with the right approach:

After initial failed attempts at cold emails, Flow found success by having messages come from existing brokers rather than generic company accounts, demonstrating the continued importance of relationships in B2B sales.

Build for the frontline decision-maker:

Flow recognized that their success depends on winning the mental battle when brokers decide how to place business. By focusing on the frontline teams' needs, they've created a compelling service that drives organic growth.

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