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Workers’ Comp Insurtech Pie Insurance Raises $11 Million

Pie Insurance, an online seller of workers’ compensation policies to small-and-medium-sized businesses, reported it has completed an $11 million Series A funding round.

The company, a full stack managing general agent (MGA) operation, currently offers its online buying process that includes an interactive pricing tool in eight states. The firm said the new new funds will be used to scale the company’s operations and to expand geographically.

Pie currently sells in Arizona, Colorado, Georgia, Illinois, Louisiana, North Carolina, Tennessee, and Texas.

The $11 million round was led by venture capital firm Greycroft, and included participation from Aspect Ventures, as well as existing investors specialty insurer Sirius Group and venture capital firms Moxley Holdings and Elefund.

Washington, D.C.-based Pie was founded in May 2017, after closing a $4.3 million seed round of funding.

Pie is headed by co-founder John Swigart, CEO, who was part of the executive team that led Esurance from a start-up to a $1.3 billion in premium online agency that Allstate acquired for $1 billion in 2011.

Pie utilizes analytics to identify risk and price policies for businesses, removing steps from the purchase process, and generating savings for many businesses. According to its predictive model, 80 percent of small businesses are overpaying for coverage, often by as much as 30 percent.

“Pie combines two elements that really stand out – a unique set of underwriting data and an experienced founder who was instrumental in building an online insurance company that was sold for over a billion dollars,” said Ian Sigalow, partner and co-founder of Greycroft.

“SMB owners are unfairly burdened by an outdated business model that requires too much of their time and effort in order to meet their insurance needs,” said Swigart. “We can remove these hurdles for a larger number of small businesses with this investment.”

The MGA accepts accounts with premiums up to $25,000, although its “sweet spot” is accounts around $5,000.


  • Workers’ Compensation Insurtech Pie Insurance Starts Selling in 4 States
  • Insurtech Pie Insurance Eyes Slice of Workers’ Comp Market with $4.3M Funding and Pricing Tool
  • The Smaller the Small Business, the Bigger the Insurance Discontent: J.D. Power

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