Getting a meeting with an insurer isn't hard. Most technology companies with a credible product and a reasonable pitch deck can secure a conversation with an innovation team, an underwriting lead, or a digital transformation director. The meeting happens. It goes well. Everyone agrees the technology is interesting.
And then nothing happens.
This is the pilot graveyard — the space between initial enthusiasm and commercial deployment where the vast majority of insurtech partnerships go to die. Having assessed dozens of technology companies targeting the insurance market, we've identified the patterns that separate companies that convert from those that stall.
The first meeting is not the hard part
Most technology companies celebrate the first insurer meeting as a milestone. It is, but not the one they think. The first meeting is a screening call. The insurer is assessing three things, none of which appear on the agenda:
Does this person understand my world? Underwriters can tell within five minutes whether someone understands insurance or is translating from a different industry. Phrases like "we can disrupt the claims process" or "our AI replaces the underwriter" are immediate signals that the technology company doesn't understand the relationship dynamics, regulatory constraints, or commercial realities of the market.
Is there a specific problem being solved? "We have data that could be useful for insurance" is not a proposition. "Our telematics data can identify the 15% of a commercial fleet portfolio that accounts for 60% of claims frequency, and here's how we'd structure a facility around that insight" is a proposition. The difference is specificity.
Would I stake my reputation on recommending this internally? The person in the meeting isn't the decision-maker. They're the internal champion — and they need ammunition to take this up the chain. If they can't articulate the value proposition in one sentence to their chief underwriter, the initiative dies in the corridor.
Why pilots stall
Companies that clear the first meeting typically enter a pilot discussion. This is where the graveyard fills up. The most common causes of pilot failure are not technical:
No defined success criteria. The pilot launches with vague objectives — "let's see what the data shows" — rather than specific, measurable outcomes. Six months later, both parties have invested time and resources, but nobody agreed upfront what success looks like. The pilot produces data but not a decision.
Wrong stakeholder in the room. The innovation team or digital transformation lead runs the pilot, but the underwriting director who controls capacity allocation was never brought in. The pilot produces results that nobody with commercial authority has bought into.
Commercial model mismatch. The technology company proposes a SaaS subscription. The insurer thinks in terms of gross written premium, loss ratios, and commission structures. Neither party has designed a commercial model that translates between these two worlds.
Compliance wasn't involved early enough. The pilot reaches the point of handling real policyholder data, and the insurer's information security team raises concerns that could have been addressed months earlier. The pilot pauses for a compliance review that nobody planned for.
What converts: the pattern
The companies that break through share a handful of characteristics that have nothing to do with the quality of their technology:
They lead with the insurance outcome, not the technology. Every conversation starts with the underwriting or claims impact, not the platform features. The technology is the "how," not the "what."
They bring insurance credibility into the room. Whether it's an advisory board member, a fractional chief insurance officer, or a consultant, there's someone on their side of the table who can speak the insurer's language. This single factor accelerates trust-building by months.
They design the commercial model before the pilot. The pilot isn't an open-ended experiment — it's a structured proof of concept with a pre-agreed commercial framework for what happens if it works. This forces both parties to be specific about value and commitment.
They engage the broker, not just the carrier. The fastest path to insurance market entry almost always runs through intermediaries. Brokers control placement, they have relationships across multiple carriers, and they're actively looking for differentiated propositions. Technology companies that go direct-to-carrier are choosing the slowest and hardest distribution route.
What to do about it
If your technology company is stuck in the pilot graveyard — or hasn't entered the insurance market yet and wants to avoid it — the diagnostic questions are straightforward:
Can you articulate your insurance value proposition in one sentence, in language an underwriter would recognise? If not, your proposition needs work before you take another meeting.
Do you have someone with genuine insurance domain expertise involved in your go-to-market? Not someone who "understands financial services" — someone who has sat across the table from an underwriter and negotiated terms.
Have you mapped the specific insurer segments, broker networks, and distribution structures that fit your technology? "Insurance" is not a market — it's dozens of sub-markets with different dynamics, buyers, and procurement processes.
Is your commercial model designed around insurance economics? If your pricing model is a standard SaaS subscription with no connection to GWP, loss ratios, or commission structures, you're creating friction at the point of commercial conversion.
The pilot graveyard isn't inevitable. But escaping it requires understanding that insurance is not a technology sale — it's a trust sale. And trust requires fluency in the buyer's language, not just the seller's.
The Connected Insurance Hub helps technology companies build the insurance expertise they need to convert meetings into partnerships. Book a complimentary diagnostic →