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How Sure Discovered Their Real Product After Insurance Executives Kept Calling Engineers Into Boardrooms

Wayne Slavin stood up mid-flight to Las Vegas and polled the passengers around him during turbulence: would you buy life insurance for 99 cents before takeoff? Everyone gripping their armrests said yes. That informal customer discovery launched what would become Sure’s decade-long journey building embedded insurance infrastructure.

In this recent episode of BUILDERS, Wayne shared how Sure pivoted from consumer mobile app to B2B infrastructure—not through strategic planning, but because insurance C-suites couldn’t stop pulling their engineering teams into meetings to see Sure’s backend operations system.

Validating Demand Before Regulatory Infrastructure

Wayne knew nothing about insurance when he started. He didn’t even carry renters insurance for his San Francisco apartment. But after that flight, he had a hypothesis worth testing through first principles: Do people want to buy insurance online? How soon before they travel do they want to buy it? How much insurance do they want to buy?

Over one weekend, Wayne built a prototype and drove paid traffic through Google and Facebook ads. The result: 15.91% conversion from ad click to purchase.

“I said, Bezos would be jealous. I have to start this business,” Wayne recalls.

That single metric justified spending the next year navigating regulatory partnerships before hiring a team. In regulated industries, launching isn’t just about building product—you need insurance carriers willing to experiment with new distribution models. Wayne spent that year as solo founder proving viability before making infrastructure investments.

When Prospects Ignore Your Product and Ask About Your Backend

Sure originally positioned as a consumer-facing mobile app aggregating insurance products. Wayne and his team built the interface, refined the user experience, and started pitching insurance companies on becoming distribution partners.

C-suite executives would review the app with standard enthusiasm. They’d encourage Sure to sell as much volume as possible. Typical response for a new distribution channel.

Then the pattern emerged.

“We would show them how we run the business on the back end behind the mobile app and behind the web and they would start calling in people into the boardroom and be like, you have got to come and see this,” Wayne explains. “We are spending hundreds of millions of dollars to try and figure this out. And these guys have figured it out already.”

After the third or fourth meeting where executives ignored the mobile app but corralled engineers to examine Sure’s operations infrastructure, Wayne recognized the signal. The backend system they’d built to run their consumer business was solving a problem insurance companies had failed to solve with hundreds of millions in investment.

“That’s when we realized, wait a second, we’re not going to be the marketing gurus, but we can be the tech gurus to do this.”

Three Failure Modes That Create Your Best Customers

Sure’s ideal customers aren’t greenfield opportunities. They’re companies that have already experienced one of three failure modes.

First: companies that attempted DIY builds and lost institutional knowledge when key engineers departed. Wayne describes these prospects matter-of-factly: “Three guys left the company, no one knows how it works. And now we are in pain.”

Second: companies that partnered directly with insurance carriers who violated fundamental partnership principles—taking customers off-platform, selling them competing products, delivering substandard digital experiences and customer service.

Third: companies that naively tried offering comprehensive choice. “Oh, well, I wanna offer my customers choice. I Wanna give them 50 options,” Wayne explains. “Well, the reality is in California right now, you don’t have 50 options. You’ll be lucky if you have two options for insurance.”

Wayne explicitly doesn’t consider prospects choosing to build as their ICP. “If that guy chose or gal chose the build option, they are not our customer because they don’t understand the reality of the environment they’re in.”

This isn’t pessimism—it’s pattern recognition from watching the same dynamic play out repeatedly over a decade.

Reframing Closed-Lost as Future Pipeline

When a prospect chooses to build, Sure doesn’t mark the opportunity as closed-lost. They mark it as “on hold.”

“Yesterday we had a call with a deal that talked to us in 2020 and they’re back,” Wayne shares. The prospect attempted their own build, lost three people who understood the system, and returned after facing the consequences.

Sure maintains what Wayne calls a “wall of shame”—tracking decision-makers who rejected Sure’s solution in favor of building. “All the people that decline to work with us don’t work at the company they were at any longer. Like they just—there’s no hero story where somebody said, hey, we’re not going to go with Sure and we’re going to do this without Sure. And they’re wildly successful.”

For infrastructure plays with extended sales cycles, this approach transforms how you think about pipeline management. Build-path prospects aren’t losses—they’re future customers who need to experience failure firsthand before understanding the value proposition.

Trading Stable Budgets for Career-Ending Execution Risk

Wayne developed a framework for understanding why enterprise buyers make seemingly irrational build-versus-buy decisions. The problem isn’t lack of information—it’s misaligned internal incentives.

“Enterprise buyers face perverse incentives,” Wayne explains. “The more people I can get, the more resources I can marshal, the more budget I can get, the better it is—misunderstanding that they’re trading their somewhat secure job at a big company where they have budget, they have people, they have job security, they’re trading that for execution risk. And execution risk is how you get fired.”

Large enterprises fund buy decisions that derisk execution. They resist funding build initiatives with uncertain outcomes—but individual decision-makers push for build projects because marshaling resources signals influence internally.

The insight: don’t argue product superiority. Help champions understand the personal career implications of their choices.

“We’ll pay Salesforce a bajillion dollars a year to do that thing. Why? Because it works. It works. Does anybody really love it? No, but it works. It’s not a failed IT project. It is a stable IT project,” Wayne says.

Matching Corner Radius and Loader Effects

Sure’s competitive differentiation isn’t technical performance. It’s their ability to become invisible within partners’ existing product experiences.

“If the way your product works is that you pop up a modal or you do it this way, or your corner radius works like this, or you have this effect for your loader, we are just going to match whatever that company has done so that their product team doesn’t have to deal with this insurance thing,” Wayne explains.

This chameleon approach requires maintaining deep product expertise across different technology stacks and design systems. But the result is customers completing complex insurance purchases without touching their keyboard—all information pre-filled from partner data, all interactions matching the host product’s existing patterns.

“We literally call out that you are buying this complex insurance product without touching your keyboard. Like, you are not entering any information. You are not typing in your driver’s license number,” Wayne says.

For embedded solutions, this level of integration depth matters more than raw performance metrics. Product teams who’ve invested years refining their user experience won’t accept partners who break their carefully crafted flows.

The Vertical Integration Roadmap

Wayne is building Sure on a twenty-year timeline with a clear thesis: “The next 20 large, let’s call it Geico sized insurance businesses will be built by consumer brands, tech brands and they have a right to win and they’re not gonna build it themselves. Cause it’s just too much of an investment to build themselves—too much infrastructure.”

Sure’s evolution follows a vertical integration path—moving from collaborative partnerships with traditional insurance carriers toward turnkey solutions that eliminate legacy carrier dependencies entirely.

The economic model changes fundamentally in embedded insurance. “We’re going to deliver longer retained customers. We have a lower acquisition cost because our partner pays for the acquisition. There is no super bowl ad, there is no Google Ad. They’re already in the product. So the acquisition cost is zero.”

Sure is now working with sovereign wealth funds and private equity firms—financial backers who want exposure to insurance economics without operating traditional insurance companies. These partners provide the capital requirements for insurance underwriting while Sure provides the technology infrastructure and brand partnerships.

It’s the same playbook Netflix executed moving from content distributor to content creator, or Amazon moving from logistics customer to logistics provider. When your partners consistently fail to meet your requirements and you’ve already solved the hardest problems, vertical integration becomes inevitable.

Wayne’s long-term vision: infrastructure enabling major consumer brands to operate insurance businesses at scale, fundamentally shifting how insurance moves from offline agent-based distribution to online embedded transactions. AppleCare already demonstrates the model at multi-decabillion dollar scale—embedded into device selection flows alongside storage, color, and financing options.

The opportunity isn’t building another insurance carrier. It’s providing the technology rails that let brands with millions of customers become insurance businesses without spending a decade building infrastructure themselves.