# John Swigart

> John Swigart is the co-founder and CEO of Pie Insurance, a Washington, D.C.- and Denver-rooted commercial insurer focused on small businesses. An economics graduate of Haverford College, he moved from finance to marketing at Esurance, served as chief marketing officer at RapidAdvance, and co-founded Pie with Dax Craig in 2017. His story is distinctive for its timing and temperament: he became a first-time founder in his 40s, used long insurance experience to enter an overlooked market, and has spoken candidly about delegation, fundraising rejection, layoffs, and the shift from growth to profitability.

- **Role:** Co-Founder and CEO at Pie Insurance
- **Organizations:** Pie Insurance, RapidAdvance, Esurance, Hope Institute, Hope Unlimited for Children
- **Education:** B.A. in Economics, Haverford College
- **Known for:** Helped grow Esurance from $30 million to $1.3 billion in written premium as chief marketing officer., Was part of Esurance's executive team when the company was sold to Allstate for $1 billion in 2011., Co-founded Pie Insurance in 2017 and led it through more than $615 million in disclosed capital raises by September 2022.

## Career timeline

- **2000-2003** — Served as chief financial officer at Esurance, leading its financial functions.
- **2003-2013** — Moved into the chief marketing officer role at Esurance and helped grow written premium from $30 million to $1.3 billion.
- **2011** — Esurance was sold to Allstate for $1 billion while Swigart was part of its executive leadership.
- **Before 2017** — Served as chief marketing officer at small-business fintech RapidAdvance.
- **2017** — Co-founded Pie Insurance with Dax Craig, operating from small offices in Washington, D.C., and Denver.
- **2018** — Pie sold its first workers' compensation policy in March and signed its first agency partner in June.
- **2020** — Named an EY Entrepreneur Of The Year Mid-Atlantic Award winner.
- **2022** — Pie raised a $315 million Series D, bringing disclosed capital raised to more than $615 million.
- **2023** — Pie transitioned to a full-stack carrier and announced expense reductions, including a 14 percent workforce reduction, in pursuit of profitability.
- **2024** — Discussed Pie's AI-driven small-business insurance work at the NYSE 2024 IPO Summit.
- **2025** — Appeared on Not Another CEO to discuss decision ownership, leadership transitions, fundraising and founding a company later in life.

## Achievements

- Helped grow Esurance from $30 million to $1.3 billion in written premium as chief marketing officer.
- Was part of Esurance's executive team when the company was sold to Allstate for $1 billion in 2011.
- Co-founded Pie Insurance in 2017 and led it through more than $615 million in disclosed capital raises by September 2022.
- Led Pie's development from an agency model toward a full-stack insurance carrier.
- Won the 2020 EY Entrepreneur Of The Year Mid-Atlantic Award.
- Was named a Washingtonian Tech Titan in 2021.

## Latest updates

- **2025-06** — Appeared on the Not Another CEO podcast to discuss founder involvement, decision ownership, board construction, fundraising and Pie's pivot toward profitability.
- **2025-04** — Pie expanded commercial auto coverage to Pennsylvania and Texas.
- **2025-02** — Co-founder Dax Craig announced his departure from Pie; Swigart remained co-founder and CEO.
- **2024-10** — Discussed insurer-investor alliances and insurtech growth in an AM Best interview.
- **2024** — Joined NYSE Floor Talk at the 2024 IPO Summit to discuss AI-driven insurance for small businesses.

## Links

- Website: https://www.pieinsurance.com
- LinkedIn: https://www.linkedin.com/in/johnswigart
- Twitter/X: https://twitter.com/pie_insurance
- YouTube: https://www.youtube.com/watch?v=FaSJpOfvNQ4
- Facebook: https://www.facebook.com/PieInsurance/

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Profile page: https://yespress.io/john-swigart
Published by YesPress — https://yespress.io
Last updated: 2026-09-26