Scout InsurTech Spotlight with Tim Ross

Tim Ross is an Entrepreneur, Experienced Business Owner and InsurTech Business Leader with a track record of building and scaling organizations across the insurance and technology landscape. Tim was interviewed by Michael Fiedel, Co-Founder at Scout InsurTech and Co-Founder at PolicyFly, Inc.

Tim, what do you see as the biggest knowledge gap between startups trying to break into insurance and the established carriers they’re hoping to serve?

“The biggest gap is perspective. Startups run on velocity, they learn by moving fast. Carriers run on stability, they protect scale through control. One sees speed as progress; the other sees it as risk. It’s not a technical gap, it’s a gap in context. Both sides are capable, but they operate at very different rhythms. Startups often underestimate how many layers shape carrier decision-making from regulatory and portfolio management to reinsurance and corporate compliance. Those structures are built to maintain stability and compliance, which are vital in this industry. Startups, by contrast, are used to quick decisions and constant iteration. That pace just doesn’t align with how carriers are designed to function.

What’s also true is that carriers sometimes underestimate how quickly startups can learn and adapt. The speed at which they can test, refine, and evolve ideas is something many insurance organizations don’t fully appreciate. It’s a two-way misunderstanding, and both sides need to think more like the other.

I like to think of it as feature velocity versus portfolio stability. Startups are focused on building features quickly and learning as they go, while carriers are managing an entire portfolio of risk and can’t afford to destabilize it. The key is finding the middle ground between those two perspectives. For startups, that means learning to translate their innovation into insurance language. You need to connect your value directly to loss ratio improvement, because that’s the metric carriers care about most. The ultimate question is simple: will this improve my loss ratio? If you can answer yes, you’re speaking their language.”

What lessons have you learned about how to innovate from within a large, risk-averse organization?

“Successful innovation inside a large company needs to look like protection, not disruption. New ideas can’t feel like they threaten the core business. They should reinforce it, strengthen it, and make it more resilient. Within carriers, innovation has to be framed as a way to make the organization safer and more efficient, not as an attempt to break the system.

Every idea needs to connect to measurable business value. That means understanding what your audience values most. Different groups within a company often have their own priorities, so you have to tailor your approach to match what matters to them.

A lot of startups assume insurers lack ideas. That’s not true. Insurance companies are full of ideas, but they focus on protecting the core, not disrupting it. When someone new comes in with an innovation, the first thing the organization asks is whether it will help protect what they’ve built.

Someone once told me, whatever you do, don’t knock over the system. It sounds simple, but it’s the truth. If you introduce change that destabilizes a core process, even if it’s a good idea, it’s going to be seen as a problem. The goal is to align with existing underwriting logic and operational stability. Don’t knock anything down. Make it better. When your innovation enhances the protection the company already values, you’ll find more allies and support inside the organization.”

How can leaders and entrepreneurs in insurance shift the “one-way door” mindset to recognize more “two-way door” opportunities that enable faster, lower-risk experimentation?

“Too many people treat pilots like marriage proposals when they should be treating them like coffee dates. Not every pilot has to be a permanent commitment or a high-stakes choice with consequential outcomes that can not be reversed. The lower stakes or more reversible a decision is, the easier it becomes to make.

If a project feels irreversible, people hesitate because they fear being stuck with it. But if you make it clear that the decision can be reversed, that you can roll it back if needed, then people are far more open to trying new things. That’s the mindset shift that needs to happen.

Create small, safe spaces for experimentation. Build sandboxes where people can test ideas, measure results, and change direction when necessary. When decisions aren’t final, teams gain confidence to explore. That flexibility accelerates learning.

Startups should think this way too. Run short pilots, evaluate outcomes, and don’t be afraid to pivot or stop if something doesn’t work. Scale should follow proof, not precede it.

We also need to decouple decision-making from scale. People often assume scaling means permanence, but those are separate ideas. It’s fine to test, learn, and even walk away if the timing or context isn’t right. Just because an idea is good doesn’t mean it’s good for this moment.

Innovation moves at the speed of flexibility. The organizations that learn fastest aren’t the ones that make perfect decisions, they’re the ones willing to evolve them.  Flexibility removes that fear and opens the door to genuine progress.”

Scout InsurTech Thanks Our Partners