SURE

Sure did not start as the company it is today. Wayne Slavin and his cousin Jarod Kolman launched it in 2015 with a much smaller idea, an app that sold flight and travel insurance.

Slavin was a serial founder who had already built and sold a data backup company and worked on the Barnes and Noble Nook e-reader. The flight insurance app was fine, but it was not a giant business.

So they made a bigger bet. Instead of selling insurance to consumers directly, they would sell the technology that lets other companies offer insurance.

That pivot is the whole story.

Sure is the engine, not the brand. When a car company or a retailer wants to offer insurance to its customers, it does not want to build all the messy machinery behind it.

Sure provides that machinery through software, plugged in with a few lines of code. It handles quoting, policies, payments and claims in the background.

Its partners put their own name on the front. Sure makes money by powering those programs and taking a slice of the business that flows through its platform.

Sure core product is an embedded insurance platform delivered through APIs, the software plumbing that lets two systems talk to each other. Brands use it to launch insurance programs without building their own insurance operation.

That covers everything from renters and auto to product protection. The platform handles the full life of a policy, from the instant quote a customer sees to the claim they file later.

Sure has increasingly leaned on automation and AI to speed up quoting and claims.

The pivot was the growth strategy. By switching from selling insurance to selling insurance software, Sure could ride on the back of far bigger brands.

Land a giant car or retail partner and you are suddenly reaching millions of customers. The company chased large, recognizable names in cars, retail and finance.

Each one brought a flood of customers Sure never had to acquire itself. It built its reputation as the quiet infrastructure company that lets any brand become an insurance seller overnight.

Embedded insurance sounds easy and is anything but. Sales cycles with giant partners drag on for months.

Insurance is heavily regulated in every state. And the sector cooled hard after the 2021 funding boom.

In early 2025 Sure cut around 70 jobs while it worked to raise more money, a rough signal for a company once valued above $550 million. The challenge is simple to state and brutal to solve.

Grow revenue faster than you burn cash in a business where both move slowly.

Sure raised a $100 million Series C in 2021, led by the private investment firm Declaration Partners and the Swedish investment group Kinnevik. That round valued the company above $550 million.

Earlier backers helped it survive the leap from a small flight insurance app to a real infrastructure business. The 2021 round was the high-water mark.

When the funding climate turned, Sure found the next raise a lot harder, which led to the 2025 cost cuts.