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Pie Insurance

Pie Insurance

Private
Washington D.C.FinTechhttps://www.pieinsurance.com/

Last Round

Series A

Jun 30, 2026

Est. Valuation

$2B

Total Funding Raised

$550.8M

Momentum

Top 50%

of companies Caplight tracks

Company Overview

Pie Insurance is an insurtech company that provides workers' compensation and commercial insurance solutions for small and medium-sized businesses through an automated, data-driven platform.

Sector

FinTech

Verticals

InsurTech

Business Model

B2B

Customer Profile

Services & Consulting

AI Layer

Application

Keywords

workers' compensationinsurtechsmall business insurancedigital insuranceautomated underwritingmanaging general agentMGAcommercial insurancedata-driven underwritinginsurance carrierSMB insuranceinstant quoteinsurance APIembedded insuranceonline insurance

Historical Pricing

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Caplight Momentum Score

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Pie Insurance Comparables

Compare Pie Insurance with similar companies based on industry and business-model similarity.

Pie Insurance comparables — related companies by embedding similarity
CompanySimilarityMarket Cap
Employers Holdings, Inc.
82%
Huckberry
82%
Arch Capital Group
76%

Pie Insurance Funding Rounds

Historical fundraising activity

Data table
RoundDateAmount RaisedValuationInvestorsSources
Series AJun 30, 2026
Series DSep 21, 2022
Series CMar 25, 2021
Series B ExtensionMay 28, 2020
Series BMar 5, 2019
Series A
Aug 9, 2018

Key People

Founding team and executive leadership

John Swigart

Co-Founder and CEO

Founding Team

Keith Hamshaw

Chief Executive Officer

Executive Team

Christopher Lankford

Chief Technology Officer

Executive Team

Alexander Davis

Deputy Chief Financial Officer

Executive Team

Pie Insurance Investors

Notable investors and investment history

Pie Insurance investors
InvestorRounds
Gallatin Point CapitalSeries D, Series B Extension
SciFi VenturesSeries A
Commerce VenturesSeries A
Sirius International Insurance GroupSeries A, Series B Extension, Series B
Aspect VenturesSeries A, Series B Extension, Seed, Series B
LagfeSeries D
Acrew CapitalSeries D, Series C

Market signals

Structured signals derived from secondary market and firmographic data.

  • Jun 30, 2026

    $20M round led by Lightspeed Venture Partners.

  • Oct 13, 2025

    Ford Pro Insure coverage expanded to Pennsylvania and Texas.

Pie Insurance Filings

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Pie Insurance filings preview — column headings only; records require access
TypeDateAmount OfferedAmount SoldFilingPagesDownload

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Firmographic Details

HeadquartersWashington D.C.
Employee Range278
Year Founded2017
Last FundingJun 30, 2026

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