Focusing on Insurance: Why Specialization Changes Everything

The reality is, each time we went down another layer, it drastically reduced our market, which freaked me out. I was thinking, I’ve got numbers to hit, our market is much smaller, and if I really niche down, I’m going to cut myself off from the broader market—possibly forever—because I’m only speaking to this one specific group. But in reality, the opposite is true.

You’re listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out key insights that led to their success. I’m your host, Callan Harrington, founder of Flash Growth, and I couldn’t be more excited that you’re here. Welcome back, everybody, to another episode of That Worked. I’m excited for this one. I’m testing out something a little different here. Typically, I have guests or a co-host—Sullivan and I dive deep into specific subjects. But for this one, I wanted to do a solo episode and walk through the decision-making process behind why I decided to niche into the insurance space. This isn’t going to be about all the benefits of insurance but rather why I made the decision to move the firm in that direction. So this is going to be a little different. As always, when I’m testing something new, I’d love to get your feedback.

So let’s dive into it.

This was a decision I had been pondering for a long time. If you’ve been a listener for a while, one of the most common things that come up when I ask founders about their biggest mistakes—or what they wish they had done sooner—is: “I wish I would have narrowed down my focus earlier.”

That focus could be on an industry, a service line, or a product line—whatever it is, narrowing down is something I’ve heard over and over again. And I knew this. I knew this before starting my business. As a VP of Sales and a revenue leader, I understood how critical it is to segment down to the audience that is absolutely going to get the most value from what you do. But when I started my own business, it was easier said than done. I feel like we all have this thought that we want to help everybody. But the reality is, there’s only a small subset that we can really make a significant impact on. One of the times I experienced this was in the insurance market. I think this is especially prevalent when you’re launching a new product—even more so if that product doesn’t exist in the market yet.

For us, the scenario was launching a brand-new product. It was something that wasn’t there before, and it was a pretty big breakthrough for business insurance. Traditionally, getting a quote back was a long process. Agents had to work with carriers, go through all these hoops—it was an archaic process. The company I was at built a platform to get those quotes back instantly. What used to take days could now be done in minutes. It was a big breakthrough. So in my mind, I thought all commercial insurance agents across the board would find value in this and love it. But in reality, most didn’t care—especially in the early days. Even though the product got a lot of headlines, a lot of buzz, and theoretically solved a big pain in the industry, the majority of agents weren’t interested.

As a result, I had to get more specific. This was just basic segmentation.

• First, we looked at all commercial insurance agents.
• Then, we realized that independent commercial insurance agents got more value from it than captives. A captive agent is tied to one carrier—they can only get quotes from that carrier. But independents work with multiple carriers, so they benefitted from our platform right away.
• That already cut our market down significantly.
• Next, we focused only on small commercial agents. Agents who provided insurance for large businesses didn’t need our product because those deals involved a long, customized process.
• Then we realized that old-school agencies just didn’t care. They had one or two carriers they always went to, and they intuitively knew where the rates would land. Even though our platform saved time, the friction and cost of change management just weren’t worth it for them.

So, how do we find early adopters? One of the first things we looked at was who had a modern website. That was a good starting point, and we started seeing better conversions.

Then we went even further:

• Bigger agencies with a lot of staff often had an old-school mindset, so we filtered down to agencies with 5 to 10 employees on LinkedIn.
• Not all insurance agencies were active on LinkedIn, so we looked for those that had multiple people engaged—not just the principal owner.

Each time we added another layer, we drastically reduced our market. And that freaked me out because I had numbers to hit. I kept thinking, If I really niche down, I’ll cut myself out from the broader market forever. But in reality, the opposite happened. I saw our conversions go up. I saw our growth accelerate. And I saw that once we really maximized that one particular market, we could then expand into broader markets. Even though 75% of our revenue in 2024 came from insurance—at all-time, 85% of our revenue was from insurance—I was still too afraid to pull the trigger and go all in.

A few things changed my mind.

1. Differentiation Matters

As we grew, we built credibility and started working with bigger companies. That naturally led to larger deals. But then we lost a pretty big deal—one where we had been the frontrunner.

The reason?

• We made a small mistake.
• Big firms have brand recognition and resources. When they mess up, they get the benefit of the doubt. We didn’t have that.
• But in insurance, we consistently won deals. Clients gave us the benefit of the doubt because they knew we understood their space.

2. Providing Maximum Value

Across all our clients, the ones who paid the most, stayed the longest, and got the highest ROI were almost always in insurance.

• Faster onboarding → We didn’t have to waste time learning industry basics.
• Deeper insights → We spotted opportunities early based on our experience.
• Stronger connections → Our network in insurance created win-win partnerships.

3. Simplifying the Business

This was the biggest personal impact. Niching down simplified everything:

• Networking became easier → Instead of saying, “I work with B2B founders,” I could say, “I help InsurTech companies.”
• Events became more focused → Instead of attending five different meetups, I could just go to the two that mattered.
• Content creation became clearer → Every newsletter, podcast, and blog post could now speak directly to insurance professionals.

So, last Tuesday, I made it official. I announced on LinkedIn that we were going all in on insurance. We updated the website. We’re fully committed now. And honestly? Any nerves I had about the decision have been fading fast. I wanted to share my thought process behind it. As always, I’d love your feedback. Do you like this solo episode format? Do you have any questions about why I made this decision?

Feel free to reach out—LinkedIn is probably the easiest way. And if you enjoy the show, please leave a review on Apple Podcasts or Spotify. It’s much appreciated. I’ll see you next week!