Executives/Pie Insurance CEO
John Swigart, CEO of Pie Insurance

Who is the CEO of Pie Insurance in 2026?

John Swigart is the Chief Executive Officer and Co-founder of Pie Insurance. John has held the CEO seat since 2017, and was previously Chief Marketing Officer at Rapid Finance.

Updated September 24, 2026
Time in seat
9 years
CEO since 2017
Career span
31 years
First recorded role January 1995
Founded
2017
Co-founder of Pie Insurance
Summary
  • John Swigart co-founded Pie Insurance in January 2017 and has led it as CEO ever since.
  • John Swigart was Chief Marketing Officer at Esurance from January 2003 to January 2013.
  • John Swigart sat on the board of Swiss Re from January 1998 to January 2000.

Current company

Pie Insurance

Pie Insurance is an At Pie Insurance, our mission is simple: make small business insurance affordable and as easy as pie. We specialize in workers' compensation and commercial auto insurance for small businesses across the U.S.

InsuranceHeadquartered in RemoteFounded 2017Private company

Source: Pie Insurance on LinkedIn

Career and education

John Swigart has been CEO of Pie Insurance since 2017. Before Pie Insurance, John was Chief Marketing Officer at Rapid Finance from January 2014 until January 2016.

Career

  1. Pie Insurance2017 to present
    • Co-Founder and CEO
  2. Rapid Finance2014 to 2016
    • Chief Marketing Officer
  3. Esurance2000 to 2013
    • Chief Marketing OfficerJanuary 2003 to January 2013
    • Vice President of FinanceJanuary 2000 to January 2003
  4. Swiss Re1998 to 2000
    • Director
  5. Kearney1995 to 1998
    • Associate

Sources: LinkedIn profile

Education

Haverford College, BA, EconomicsSource

Leadership team at Pie Insurance

John Swigart leads a leadership team of 12 published executives.

Most senior 5 of 12

NameTitleIn seat since
John SwigartCo-founder and CEO2017
Alexander DavisChief Financial OfficerNot stated
Chris LankfordChief Technology OfficerNot stated
Rick PoulinChief Underwriting OfficerNot stated
Carla WoodardChief Claims OfficerNot stated

Sources: Pie Insurance leadership page

Frequently asked questions

Who is the CEO of Pie Insurance?

John Swigart is the Chief Executive Officer and Co-founder of Pie Insurance. John has held the CEO seat since 2017, and was previously Chief Marketing Officer at Rapid Finance.

When did John Swigart become CEO of Pie Insurance?

John Swigart has been CEO of Pie Insurance since 2017, according to LinkedIn profile.

What did John Swigart do before Pie Insurance?

John Swigart was Chief Marketing Officer at Rapid Finance from January 2014 until January 2016, according to LinkedIn profile.

How long has John Swigart been CEO of Pie Insurance?

John Swigart has been CEO of Pie Insurance for 9 years, since 2017.

Who else leads Pie Insurance?

Alexander Davis (Chief Financial Officer), Chris Lankford (Chief Technology Officer), Rick Poulin (Chief Underwriting Officer), Carla Woodard (Chief Claims Officer), and 7 more. Source: Pie Insurance leadership page.

Reach Pie Insurance's decision makers

Find Pie Insurance's leaders at vice president level and above, with verified work emails and phone numbers in Unify.

Methodology

The seat holder is identified in Unify's professional profile dataset, then confirmed against the company's published leadership page, its SEC filings, and Wikipedia before publication. Career and education rows carry the public document they were taken from. Leadership team membership follows the company's own leadership page; in-seat dates come from filings where available and otherwise from the profile record. Company figures are read from the Unify headcount page for the same company and are profile coverage measures, never company-reported workforce totals. The employee preview lists vice president and senior vice president level profiles by department. No personal contact details are published.

Identity confirmed against Pie Insurance on LinkedIn. Last verified: September 24, 2026.