PIE INSURANCE

Pie started in 2017 with a simple gripe. Workers' comp insurance for small businesses was a mess.

Slow quotes, murky pricing, and small employers getting overcharged because nobody bothered to price them properly. John Swigart, who came from the online insurer Esurance, teamed up with Dax Craig, who had founded an insurance analytics firm called Valen.

Between them they had the insurance chops and the data chops. The plan was to use data and automation to give a small business a fast, fair workers' comp quote online.

No agent, no waiting, no mystery pricing.

Pie sells workers' compensation insurance to small businesses. That is the coverage that pays out when an employee gets hurt on the job, and most states require it by law.

A bakery, a landscaper, a small contractor. They go to Pie, answer some questions, and get a quote fast.

Pie makes money on the insurance premiums. In the early days it acted as a middleman, placing the risk with partner insurers.

Then in 2023 it became a full-stack carrier, meaning it underwrites and pays claims itself. More risk, but more of the profit.

The core product is workers' compensation insurance for small businesses, quoted online in minutes. Around it Pie built a quoting and servicing platform for both direct customers and the insurance agents who sell on its behalf.

It has also expanded into commercial auto insurance. The pitch stays the same throughout.

Fast, fair, data-driven coverage for small companies the big insurers treat as an afterthought.

Pie grew by picking one boring niche and owning it. Workers' comp for small businesses is unglamorous, which is exactly why it was underserved.

Pie expanded state by state across the US, added agent and partner channels, and slowly climbed the value chain. It started as a middleman, then in 2023 became its own rated insurance carrier with an A- financial strength rating.

It has also pushed into nearby products like commercial auto. Same customer, more ways to sell them coverage.

Becoming your own insurance carrier cuts both ways. Pie now underwrites its own policies, so if it misprices risk and claims come in high, it eats the losses.

That is the hard part of insurance. You only find out if your pricing was right years later.

Workers' comp is also a cyclical, competitive market full of deep-pocketed incumbents. And scaling a carrier eats capital, which is why Pie kept raising huge rounds.

Profitable underwriting at scale is the whole game, and it is not won yet.

Pie raised money from a mix of venture and insurance heavyweights. Greycroft led the early Series A in 2018.

SVB Capital led a $45 million Series B in 2019. Then the insurance giants showed up.

Allianz X, the venture arm of Allianz, co-led the $118 million Series C in 2021 and came back for more. The big one landed in 2022.

Centerbridge Partners and Allianz X co-led a $315 million Series D, with White Mountains and others joining. When traditional insurers fund an insurtech, it usually means the tech works.