By Aclaimant

Sep 17, 2026

Category: InsureTech / Agency Growth / Leadership Author: Aclaimant Team

The insurance industry is full of people who "fell backwards" into their careers and stayed for twenty years. But while the industry is excellent at retaining talent, the gap between average performers and top-tier market leaders is massive.

In our latest Aclaimant Fireside Chat, we sat down with Callan Harrington, a veteran of six Insurtech startups (resulting in three exits and three flops) and the founder of the strategy agency Flash Growth. Through his consulting work and his Insurance Growth Lab podcast, Callan has spent years deconstructing the habits of the most successful agencies and tech founders in the space.

Here are the three defining traits of top performers in the modern insurance landscape.

1. They Take Contrarian Risks and "Bet the Farm"

Top performers rarely win by simply grinding twice as hard on the exact same strategy as their competitors. They actively seek out contrarian approaches.

Callan points to Matic Insurance as a prime example. While the entire industry was fiercely competing for new home leads by partnering with real estate agents and loan originators, Matic pivoted. They focused on the loan servicing side of the business—a space with much lower immediate buyer intent, but vastly less competition. By figuring out how to make that specific channel work, they built a massive, scalable moat.

Whether it is targeting struggling rural agencies for acquisition when everyone else wants high-growth urban firms, or driving 80% of B2B carrier leads through paid media rather than buying expensive trade show booths, top performers find the neglected angle and double down on it.

2. They Leverage Proprietary Data

Generative AI is changing the landscape, but it has severe limitations. Today, anyone can ask an AI model for general industry advice. To stand out, you must provide insights the AI cannot access.

During his time at Bold Penguin, Callan’s team used internal exchange data to release a report showing a massive spike in hair salons shopping for insurance just as COVID restrictions began to lift. That proprietary data was incredibly valuable to their partners because it was entirely unique. If you want to differentiate in the AI era, you must utilize your own internal, closed-loop data to provide insights that ChatGPT cannot scrape.

3. They Lean Into the "In-Person" Premium

As AI drastically lowers the cost of creating high-quality content, digital channels are going to become overwhelmingly noisy. How do you stand out when every competitor can generate flawless articles and videos?

Callan quotes author Tim Ferriss to answer this: "The only thing you can do is go do interesting things and tell people about it."

Because digital content will be ubiquitous, the value of true, in-person relationships will skyrocket. The industry will revert to high-trust, peer-to-peer networking. The winners of the next decade will be those who use AI to orchestrate their administrative tasks, freeing them up to spend maximum time shaking hands and building real-world relationships.

Watch the full interview here