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2-Year-Old Pie Insurance Raises $45M to Launch a National Expansion


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Analysts at Research and Markets predict that the global insurance market will reach $1.11 billion by 2023, and a niche D.C. startup wants its piece of the pie.

Pie Insurance, a provider of workers' compensation insurance for small businesses, has closed a $45 million Series B round less than a year after its first sale.

The company says it will use the funds to expand geographically and add new distribution sources toward its goal to expand nationally by the end of 2019.

Participating investors in the round included SVB Capital, Sirius Group, Greycroft, Moxley Holdings, Aspect Ventures and Elefund. Pie has raised $61 million in capital since its founding in 2017, including an $11 million Series A round in July last year.

The new funding reflects a trend of fewer, more valuable venture capital deals in the region. Just 11 months after selling its first policy, this is about as early as it gets – but for good reason.

Pie claims it has generated nearly $10 million so far in written premiums from thousands of small businesses, and it operates in 19 states. It's currently available in Maryland, but not Virginia or D.C., according to its website.

“In addition to their strong growth, Pie has produced outstanding underwriting results,” Greycroft partner Ian Sigalow said in a statement. “The company is positioned to make a huge impact on the small business market for commercial insurance.”

CEO John Swigart, a former Esurance executive, told the WBJ that 11 of the firm's 50 employees work in its District headquarters, but that will expand to 25-30 by yearend.


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