10 Years to Build a $550M InsurTech: How Sure's Wayne Slavin Pivoted From Flight Insurance to Embedded Insurance for Tesla and Toyota

In 2015, Wayne Slavin had a crazy idea on a flight to Vegas: sell life insurance to people freaking out during turbulence.

One weekend later, he built a prototype. No actual insurance product. Just a landing page, some Google ads, and a fake payment error at checkout.

Fifteen point nine one percent of people who clicked an ad went through the entire process—entering flight details, beneficiary information, even a final message to loved ones—and tried to pay $19.99 for a million dollars of coverage.

Some people came back seven times trying to make the payment work.

"Jeff Bezos would be jealous," Wayne thought. "We need to go start this business."

Today, ten years later, Sure has raised over $123 million and reached a valuation of $550 million. The company has been profitable since 2019, powers embedded insurance programs for Tesla, Toyota, MasterCard, and Intuit, and operates as the infrastructure layer enabling Fortune 500 companies to launch their own insurance businesses.

But the journey from selling $20 flight insurance to powering billion-dollar insurance programs took a decade—far longer than Wayne ever imagined.

"Oh no, no, no, no, no," Wayne said when asked if he expected it to take over ten years. "There's no way you would sign up for ten years... I just happened to unknowingly choose an industry that a decade is equivalent to a year in other industries."

Key Takeaways

• Wayne's weekend prototype achieved 15.91% conversion from ad click to attempted purchase
• Sure was founded in 2015 by Wayne Slavin and Jarod Kolman
• Wayne worked solo for an entire year before raising $1.6M seed round
• First launched in South Africa (easier regulatory environment) before expanding to US
• Spent ~18 months on flight insurance before pivoting to renters insurance, then auto
• Raised $100 million Series C in October 2021 led by Declaration Partners and Kinnevik at $550M valuation
• Company has been profitable since 2019
• In 12 months leading to Series C, Sure more than doubled revenue and team size
• Haven't raised since 2021—still operating on that capital four years later
• Powers insurance for Tesla, Toyota, MasterCard, Intuit, Betterment, Carvana, Farmers, Chubb
• Sells both to brands (B2B2C) and directly to insurance carriers (B2B SaaS)

Table of Contents

1. The Weekend Prototype: 16% Conversion on Fake Insurance
2. One Year Solo: From San Francisco to South Africa
3. The First Real Launch (And a Production API Key Mistake)
4. Why Flight Insurance Hit a Wall
5. The Slow Pivot to Embedded Insurance
6. The Tesla Moment: When PMF Became Obvious
7. From Software to Full-Stack Insurance Platform
8. Why Sure Hasn't Raised Since 2021

The Weekend Prototype: 16% Conversion on Fake Insurance

Wayne Slavin came from payments and e-commerce. He was VP of Product at a company that had won TechCrunch's most innovative company of the year in 2013.

But he had a hypothesis: insurance would eventually be sold like every other product online. Why wouldn't it be?

On a flight to Vegas for a conference in 2014, inspiration struck. People around him were visibly terrified during turbulence. Planes are statistically very safe, but in that moment, people felt vulnerable.

"I wonder if we could sell them life insurance right before the plane took off," Wayne thought.

That long weekend when he wasn't feeling well, he built a prototype. Registered a domain. Threw together a WordPress site. Created a singular offer: buy life insurance before your flight.

He tested three different coverage amounts—good, better, best. The e-commerce cornerstone. He didn't know if it should be $50,000 of coverage or $5 million.

Spent a few thousand dollars on Google and Facebook ads. Tested positive messaging ("leave money to your family") against darker imagery of plane crashes.

The sweet spot? A million dollars of coverage for $19.99.

And that conversion rate? 15.91% from ad click to attempted purchase.

The catch? There was no actual insurance. When people hit "pay," they got what looked like a credit card error.

"We saw people coming back, going through that whole process seven times to try and buy it," Wayne said. "If people are going to go through this whole thing multiple times to try and buy this product, they actually need it."

That was the validation. Now he just had to actually build the real thing.

One Year Solo: From San Francisco to South Africa

Wayne spent an entire year working alone before bringing on co-founders and raising money.

"I don't know if I would recommend it," he admitted. But his engineering and product background let him straddle different roles. More importantly: "Wouldn't want to ask anybody to leave their job and put their financials on the line until this thing was at least on stable footing."

The year was spent on two things: building enough of a product to show an insurance company, and actually landing that first insurance partner.

The challenge? US insurance is incredibly complicated. Every state is basically its own market with its own regulations.

So Wayne looked overseas. South Africa had several advantages:

• One market, one regulator
• English-speaking
• Massive cell phone population
• Digital banking infrastructure
• Wayne was originally from South Africa

He camped out there for seven weeks to meet with insurance companies and close a deal.

While he was gone, his now-wife moved them from San Francisco to Los Angeles. "I flew back to Los Angeles instead of San Francisco... Came back and said, OK, we're going to go launch this in South Africa."

The pitch to insurance companies was simple: "They didn't have to build anything new. We were building everything. We just needed their product to sell."

No million-dollar investment required from them. Just be the underwriter. Let us handle distribution.

That South African insurance company provided the validation to approach the same company's US counterpart. "We're already doing it with your partners. Why don't we just do it here?"

At that point, things were built. It was live in the app store. The product was real.

By the end of that year, Wayne raised $1.6 million seed round and brought on five founding team members—all people he'd worked with at previous companies. Three of those five are still at Sure ten years later.

The First Real Launch (And a Production API Key Mistake)

The launch was "anticlimactic," Wayne said. They'd been building toward it the whole year.

The memorable moment? "Always check if you're using production API keys or sandbox API keys in your production app."

They launched with Stripe keys flipped around. None of the transactions worked. They fixed it quickly and were off to the races.

The go-to-market strategy combined digital and guerrilla tactics:

• Google ads
• Facebook ads
• People standing at airports

"You got to get people at high intent," Wayne explained. The whole point was contextual commerce—buying insurance in the moment you need it.

His previous company had pioneered this at college campuses, enabling students to buy products while standing in line. They replicated the playbook for airports.

"We could acquire customers literally while they were standing in line... Register for the app, make their payment and transaction happen before the guy or gal standing in front of them in line did it in real life."

Why a mobile app instead of a website? Location services.

They wanted to send push notifications when you arrived at your destination—precisely 22 minutes after arrival, the optimal time they discovered through testing.

They'd built polygons around every airport in their backend system. When you landed, they knew. When the right moment came, they'd nudge you to buy insurance for your return flight.

Why Flight Insurance Hit a Wall

The product worked. They reached tens of thousands of customers in about eighteen months. Repeat usage was solid.

But the economics didn't work for a venture-scale business.

"The policies we're selling were dollars. It wasn't like tens of dollars," Wayne said. On a $20 policy, they got "a small percentage of that as true revenue."

More fundamentally: "There's no retention. It's a one-time transaction. People don't need it."

And it was a complete commodity. "If somebody sells me a million dollars for ten and somebody for twelve, I'll take the ten all day."

There are companies today that do travel insurance well. But Wayne realized: "That was not that exciting."

The insight that changed everything? "Small dollar things work really well if you have no CAC. Sell a dollar thing all day long, no problem. But when you have to go acquire the customer and they're not repeat, and it's not recurring—man, that is hard."

The Slow Pivot to Embedded Insurance

Post-seed, pre-Series A, Sure started building what would become their real business: embedded insurance.

Instead of acquiring customers themselves, they'd partner with companies that already had customers. Sell insurance at the point of need, integrated into existing flows.

"It's in a sense no longer a commodity," Wayne explained. "You're not really competing with others since it's part of some flow. It becomes a checkbox."

They started with renters insurance for people moving into apartments. Customers: property management software platforms, places you find apartments online and pay rent.

The key decision: they didn't immediately kill the mobile app.

"Maybe that's an unorthodox thing, but while continuing to support the mobile app strategy... I hadn't proven the embedded insurance thing yet."

They kept one thing going while validating the second. Slowly sunset the mobile app as embedded distribution ramped up.

"It sounds trivial to go from people in airports driving app downloads to signing enterprise contracts. But you have to be sure you can do that, and that is a skill in of itself."

They added more distribution partners. Saw the conversion work. Saw the economics were far better.

Then insurance companies themselves started asking to use Sure's platform. They needed the same infrastructure to digitize their own offerings.

Sure started selling SaaS licenses to insurance companies wanting to build embedded programs.

"Effectively, that's what we do today," Wayne said. "We are the software solution for the insurance companies... and we are actually the full end to end."

Sure became both the front-end transaction layer (embedded in brands like Toyota) and the back-end software (powering the insurance companies and underwriters).

The Tesla Moment: When PMF Became Obvious

Wayne has witnessed different levels of product-market fit across Sure's evolution. The weekend prototype. South Africa. Renters insurance.

But one moment crystallized everything.

"End of August 2019, there was a tweet from the chief tweeter, and a program launched. And it was a rocket ship. Literal rocket ship of insurance transactions, sales."

Sure had been working with Tesla over the past year, and the EV maker provided buyers the option of purchasing insurance on Sure's platform embedded into Tesla's online car-buying experience.

"If you have the right brand and the right product in the right place, this is going to be a billion dollar business," Wayne realized.

Auto insurance was the inflection point. "Obviously, bigger ticket item. We went from single-digit dollars to double-digit dollars to triple-digit dollars."

"There was just a stampede of demand for easy to buy auto insurance... That was the thing in my brain that crystallized, oh my God, this will not just work, this will truly work."

That validation led to the conviction: "Deca billion dollar insurance brands will be built by Sure."

Everything since 2019 has focused on signing the world's biggest brands to build insurance programs on Sure's platform.

From Software to Full-Stack Insurance Platform

Between 2019 and today, Sure evolved from pure software to a complete solution.

"Every year we've gone from, hey, we're going to give you the software to do this... to at this point in 2026, we literally can go to the world's biggest brand and say: we have every single piece to launch your own insurance business in one place."

The pitch today: "You do not need staff, you do not need software, you do not need balance sheet, you do not need a capital partner, you don't need anything. We are a one-stop shop."

Sure now provides:

• Software infrastructure
• Implementation services
• Operations
• Balance sheet and capital
• Underwriting capabilities

"This is not a situation where someone says, we're going to switch from one type of manufacturing to 3D printing. They've never sold insurance before. They don't know how to underwrite insurance."

They can't go to their CFO asking for a billion dollars when they've sold zero policies. "That's just not how business works."

Sure built a unique model where they can stand up an insurance brand for a Fortune 500. The brand markets it (their core competency). Sure makes everything else work. Capital partners provide the balance sheet to underwrite risk.

"Everybody gets what they want."

The thesis is simple: consumers want to buy from brands they trust. Capital providers love insurance returns (Warren Buffett built Berkshire Hathaway on it). Sure connects the two.

"Why wouldn't we go help people expand that market and launch new insurance brands?"

Why Sure Hasn't Raised Since 2021

Sure raised $100 million in Series C in October 2021 led by Declaration Partners and Kinnevik. Four years later, they still haven't raised again.

"I think, being financially responsible," Wayne explained.

When they raised Series C, "we had every dollar of our Series B in the bank still and we were actually profitable, net income positive."

This was 2021, when profitability was deeply unfashionable. "People were like, ew, what is profit? But it turned out that was a good discipline to have."

They've been investing that $100 million diligently to build the full-stack platform they have today.

"I've always just wanted to control our own destiny. And it's hard to control your own destiny when you're starved for oxygen. You don't tend to make the right long-term decisions."

The real answer? "I haven't needed to raise."

Though Wayne hints: "Even though I could certainly do more interesting things if you did raise... TBD, stand by for some cool stuff."

Frequently Asked Questions

Who is Wayne Slavin?

Wayne Slavin is the co-founder and CEO of Sure, an insurance technology company. He founded Sure in 2015 alongside Jarod Kolman. He originally worked in payments and e-commerce before starting Sure.

What is Sure and what does it do?

Sure is an insurance technology company that enables companies to embed insurance into their customer journey and powers the digital offerings of insurers, creating seamless, convenient, and personalized insurance experiences.

How much funding has Sure raised?

Sure has raised $123 million total, including a $100 million Series C round in October 2021 that valued the company at $550 million.

Who are Sure's investors?

Sure's investors include Declaration Partners, Kinnevik, WndrCo, FTAC Ventures, Expanding Capital, W.R. Berkley Corporation, and Menlo Ventures.

Is Sure profitable?

Yes, Sure has been profitable since 2019, which is unusual for a venture-backed company, especially during the 2019-2021 period.

What companies use Sure's platform?

Sure's customers include Tesla, Farmers Insurance, Chubb, Intuit, Betterment, Revolut, Carvana, several automotive manufacturers, and a leading global credit card network.

Why did Wayne spend a year working alone?

Wayne spent a year solo to de-risk the business before asking others to leave their jobs. He needed to land an insurance partner and have enough product to show investors before bringing on founding team members.

Why did Sure launch in South Africa first?

South Africa offered a simpler regulatory environment (one market, one regulator instead of 50 different US states), was English-speaking, had strong digital banking infrastructure, and Wayne was originally from there.

What was Sure's original product?

Sure originally sold life insurance to people before they boarded flights, capitalizing on the fear people feel during air travel. Policies cost around $19.99 for $1 million in coverage.

Why did Sure pivot away from flight insurance?

Flight insurance was too small ($20 policies), had no retention (one-time transactions), was completely commoditized, and required high customer acquisition costs that didn't work with low policy values.

Want More Founder Stories Like This?

This article is based on an episode from The Product Market Fit Show, where host Pablo Srugo interviews successful founders about their journeys from zero to PMF and beyond.

Listen to the full conversation with Wayne Slavin to hear more about the guerrilla marketing tactics at airports, why embedded insurance is like the Delta Amex card, his advice on finding your "why" sooner, and what keeps him up at 4 AM even after ten years of building.

🎧 Listen to the episode here