/Companies

Pie Insurance

United States, US · Founded 2017 · Delaware corporation · 379 employees on LinkedIn · 13 known investors

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Pie Insurance is an insurtech company providing property and casualty insurance solutions. The company serves small to mid-sized businesses in the United States.

Also known as Pie Insurance

Founders & leadership

Pie Insurance was founded in 2017 by John Swigart and Dax Craig.

JSJohn Swigart
John SwigartFounderJohn Swigart is co-founder and CEO of Pie Insurance, an insurtech company providing property and casualty insurance to small and mid-sized businesses in the United States.
DCDax Craig
Dax CraigCo-Founder and President2018–2025Dax Craig is Co-Founder and former President of Pie Insurance, an insurtech company providing property and casualty insurance solutions to small and mid-sized businesses, and currently Co-Founder and CEO of Comeryx Insurance. He has over two decades of experience in insurance and technology.
JM
Joel MoxleyExecutive
KO
Kip ObertingNamed on SEC filing

Board

ISIan Sigalow
Ian SigalowBoard MemberCo-Founder & Managing Partner at Greycroft

Investors · 13

Reported raises · per SEC filings

Form D private placements

$375.4M disclosed across 4 rounds · 2017–2022

▶$314.3MraisedOct 2022 · 29 investors · Insurance
Rule 506(b)
Officers, directors & promoters on the filing
  • Kristina JohnsonDirector
  • John SwigartExecutive Officer, Director
  • Westley ThompsonDirector
  • Dr. Nazim CetinDirector
  • Teresa LeonExecutive Officer
  • Ian SigalowDirector
  • Thomas GrossiExecutive Officer
  • Kirsten WolbergDirector
  • Justin BrendenDirector
  • Laura BishopDirector
  • Eric HoffmanDirector
  • Dax CraigExecutive Officer, Director
Offering amount
$400M
Amount sold
$314.3M
First sale
Sep 2022
Incorporated
Corporation, Delaware
Federal exemptions
06b
Full filing on SEC EDGAR ↗
▶$45MraisedMar 2019 · 17 investors · Insurance
Rule 506(b)
Officers, directors & promoters on the filing
  • Kip ObertingDirector
  • Dax CraigDirector
  • Joel MoxleyDirector
  • Ian SigalowDirector
  • John C. SwigartExecutive Officer, Director
Offering amount
$45M
Amount sold
$45M
First sale
Feb 2019
Incorporated
Corporation, Delaware, 2017
Federal exemptions
06b
Full filing on SEC EDGAR ↗
▶$11MraisedAug 2018 · 15 investors · Insurance
Rule 506(b)
Officers, directors & promoters on the filing
  • Joel MoxleyDirector
  • Ian SigalowDirector
  • Kip ObertingDirector
  • John C. SwigartExecutive Officer, Director
  • Dax CraigDirector
Offering amount
$11M
Amount sold
$11M
First sale
Jul 2018
Incorporated
Corporation, Delaware, 2017
Federal exemptions
06b
Full filing on SEC EDGAR ↗
▶$5MraisedAug 2018 · 8 investors · Insurance
Rule 506(b)
Officers, directors & promoters on the filing
  • John C. SwigartExecutive Officer, Director
  • Joel MoxleyDirector
  • Dax CraigDirector
  • Kip ObertingDirector
Offering amount
$5M
Amount sold
$5M
First sale
Oct 2017
Incorporated
Corporation, Delaware, 2017
Federal exemptions
06b
Full filing on SEC EDGAR ↗

Source: SEC EDGAR Form D. Amounts as filed; amended filings shown once at their latest values.

Company profile

researched Aug 2026

Pie Insurance is an insurance technology company focused on property and casualty coverage for small and mid-sized businesses in the United States. Its principal advertised product is workers' compensation insurance, which small business owners can quote and purchase online, with policy management handled through an online customer account.

The company states that its workers' compensation coverage is available in 39 states and Washington, D.C., with additional states planned. It markets a quoting flow that produces a price in about three minutes and advertises potential savings of up to 30% on workers' compensation premiums, positioning its data-driven underwriting technology as the basis for pricing and coverage.

Business model

Pie Insurance provides property and casualty insurance products, primarily workers' compensation, to small business customers. It sells directly to business owners online and also operates a partner program for insurance agents who place coverage with Pie.

▸Full profile — market position, technology, go-to-market, geography

Market position

Pie positions itself on speed and price for small commercial insurance buyers, citing a three-minute online quote, self-service policy monitoring, and advertised savings of up to 30% on workers' compensation relative to alternatives.

Technology

The company describes data-driven insurance technology used to price and structure coverage, supporting an online quoting experience that it says returns a quote in roughly three minutes, alongside a self-service online account for monitoring policies.

Go-to-market

Two channels are presented on the company's site: a direct digital channel where small business owners obtain an online quote and manage coverage through an account, and an agent channel inviting brokers and agencies to become Pie partners.

Small and mid-sized businesses in the United States that need workers' compensation and related property and casualty coverage, plus the insurance agents who serve them.

Geography

United States only, with workers' compensation coverage available in 39 states and Washington, D.C. and stated plans to add more states.

Compiled by commissioned research from 1 cited public sources — announcements, filings, and press listed under research sources below.

Key figures

latest reported
Advertised quote timeJan 20243 minutes
Advertised savings on workers' compJan 202430%
HeadcountAug 2026379
States servedJan 202439 states plus Washington, D.C.

Company-reported or press-reported figures, each dated to when it was claimed — not independently audited.

Founder mafia

5 people who came through Pie Insurance went on to found or lead other companies.

Related companies · 4

Companies working in the same space as Pie Insurance.

Legal entities · 1

corporate structure
Pie InsuranceDelaware

▸Research sources · 1

primary sources listed

1 public sources were cited for this profile; the first-party ones are listed here.

Frequently asked questions

What does Pie Insurance do?
Pie Insurance is a U.S. insurtech offering data-driven workers' compensation and property and casualty coverage to small businesses.
Who founded Pie Insurance?
Pie Insurance was founded by John Swigart, Dax Craig in 2017.
Who are Pie Insurance's investors?
Pie Insurance's investors include Allianz X, Greycroft, Acrew Capital, Aspect Ventures, Elefund, Evolution VC Partners, Gallatin Point Capital, Khosla Ventures and 5 more.
How much funding has Pie Insurance raised?
Pie Insurance has disclosed $375.4M raised across 4 rounds.
Where is Pie Insurance headquartered?
Pie Insurance is headquartered in United States, US.