About John Swigart

John Swigart as CEO and Co-founder of Pie Insurance, John Swigart is responsible for overseeing all aspects of the company. Since the company was founded in 2017, John has led Pie to become one of the fastest growing insurtechs in the United States, expanding its workers’ comp insurance offering to 38 states and Washington D.C, raising more than $300 million in funding, and growing the company’s headcount to more than 400 team members across the country. Prior to founding Pie, John was the chief marketing officer at RapidAdvance, a small business fintech that’s part of a family of companies including Quicken Loans, Fathead, and the Cleveland Cavaliers. In addition, he spent 13 years as an executive team member at Esurance, where he initially led all of the financial functions from 2000-03 as the company’s chief financial officer, and then grew the company from $30M to $1.3 billion in written premium as chief marketing officer. Under his leadership, the company was sold to Allstate in 2011 for $1 billion. John holds a B.A. in economics from Haverford College. He is an active board member for Hope Unlimited for Children, an organization based in Brazil with a mission to transform the lives of high-risk orphans and vulnerable children and break the cycle of poverty.