🧩 The #1 Mistake Sales Teams Make with Risk-Averse Clients

In my more than three decades of leading insurance service-related companies and in my current role of consulting with start ups, I hear familiar laments: “Why does it take so long for these people to make a decision?” or “This should be a no-brainer.” I tell them they are not alone. Everyone who sells to carriers eventually runs into a similar wall: “they” are large, seemingly unsurmountable marble fortresses of wealth, and we’re aiming for just to get their attention.

The truth is simple: insurers are wired differently.

Banks and investment managers are trained to chase returns. Insurers are trained to avoid risk. And those fundamental differences shapes every decision they make.

To succeed in this market, you need to understand that they have massive responsibilities regarding capitalization, reporting, agency and field management—just appreciating for a moment their landscape- may help you adjust your approach accordingly. One of my early mentors put it this way: investment firms teach people to maximize returns; insurance companies teach people to minimize risk. That “protect the downside at all costs” mentality explains why deals often feel like … well, they’re moving through quicksand. But once you recognize it, you can change the way you sell and dramatically improve your odds of success.

Why is Opening The Door Difficult?

Several forces converge to make insurance sales uniquely challenging. Sales cycles are long—can be eighteen months + —because even small decisions demand multiple approvals, RFP processes, procurement signoffs, and legal reviews. Regulatory complexity adds more friction. With carriers in the U.S. operating under fifty different state set of regulators, it’s no wonder they approach new ideas cautiously and move at a measured pace.

At the cultural core, insurers are deeply risk averse. Every innovation triggers a litany of questions: Is this product or strategy consistent with all others existing and underway? What if regulators object? What if the provider doesn’t have the capital to continue operations after we sign an agreement and invest in them?  In many cases, standing still feels safer than moving forward. Inside the enterprise, silos complicate matters further. Underwriting, claims, IT, legal, distribution, and marketing often operate in separate lanes with their own priorities and budgets. A “yes” from one group rarely means you’re over the finish line.

Legacy technology and high switching costs present another hurdle. Integrating with COBOL-era mainframes is neither fast nor inexpensive. Even when a solution is objectively better, carriers know adoption means retraining staff, enduring downtime, and navigating compliance reviews. Layer on the industry’s sensitivity to reputation—where trust is everything—and it’s clear why carriers scrutinize every decision, particularly when working with new vendors.

Breaking Through

Winning in this environment requires a thoughtful playbook.

Start by framing your solution around the carrier’s ethos, not your product features! Do your research and learn their language.  Make your presentation shine as you connect to metrics they already track, and preferably, test your presentation with skilled pros that we have at Insurex to minimize delay or disappointment.

Then, start small. What?

Yes. Piloting in a single region or product line creates a lower-stakes entry point, delivers early proof of ROI, and builds momentum for expansion. Identify and equip an internal champion who believes in your value; give them the tools to persuade colleagues across silos. At the same time, engage IT and compliance early. If they aren’t prepared, they’ll be the first to block progress. Provide security packages, compliance documentation, and integration roadmaps upfront.

Proof matters more than promises. Carriers are fast followers, so remember that references, case studies, and real results speak louder than hype. Timing also plays a role. Avoid blackout periods like audits or budget freezes, and target Q1, when carriers are typically more open to new initiatives. And above all, make the business case easy. Executives want clear ROI math, concise one-pagers, and data that demonstrates real impact.  At Insurex, we have risk management and product specialists who can help you refine your draft presentation by asking hard questions.  Invest in that quality control process to minimize embarrassment: there is a reason why many insurers have been around for 100+ years.  They are seasoned. And thus, even twenty somethings with a remarkable product or solution can be ready to win if they are prepared, not for battle, but for impressing the potential client with your breadth of knowledge.

Pro Tip: The “Carrier Pack”

One powerful way to stand out is to anticipate their concerns before they voice them. Assemble a “Carrier Pack” that includes a one-page overview, a compliance and security summary, ROI data and case studies, an integration timeline, and an executive summary designed for leadership. By answering their risk questions proactively, you position yourself as a safer, more credible partner from day one.  Remember- one page.

Bottom Line

Selling to insurers isn’t about chasing quick wins. It’s about patience, credibility, and trust. The sales cycle will always be slower than in other industries, but the payoff is significant. Once you win a carrier, they become one of the most loyal, long-term customers you can have.

Approach them on their terms—risk first, transformation second—and you’ll not only shorten your sales cycle but also build enduring partnerships that deliver lasting value.

We are eager to help you thrive.