# Darryl Rawlings

> Darryl Rawlings is the Canadian founder and chair of Trupanion, a Seattle-based public company. He financed its early development with proceeds from selling the Canadian Cigar Company, led Trupanion through its 2014 IPO, and remained CEO until Margi Tooth succeeded him in August 2024.

- **Role:** Founder & Chair of the Board at Trupanion
- **Organizations:** Trupanion, Canadian Cigar Company, Naked Wines (former chair and director), North American Pet Health Insurance Association (founding member)
- **From:** Vancouver, Canada
- **Nationality:** Canadian
- **Education:** Diploma of Marketing Management, British Columbia Institute of Technology
- **Known for:** Founded and built Trupanion into a publicly traded company., Led the company through its July 2014 IPO., Annual Trupanion revenue exceeded $1 billion during his leadership.

## Career timeline

- **Early 1990s** — Worked in technology sales to the cellular industry.
- **1994** — Founded the Canadian Cigar Company, according to his Crunchbase biography.
- **1998** — Sold his cigar business and began developing Trupanion, originally Vetinsurance International.
- **2000** — Trupanion issued its first policy in Canada to his dog Monty.
- **2007** — Moved his family to Seattle.
- **2008** — Trupanion expanded into the United States.
- **2014** — Led Trupanion through its July IPO.
- **2015** — Won an EY Entrepreneur Of The Year Pacific Northwest award in financial services.
- **2021** — Joined Naked Wines as an independent non-executive director; subsequently became chair.
- **2022** — Stepped down as Naked Wines chair in October.
- **2023** — Assumed Trupanion board chair role on January 10.
- **2024** — Left Trupanion CEO role effective August 1; remained director and chair.

## Achievements

- Founded and built Trupanion into a publicly traded company.
- Led the company through its July 2014 IPO.
- Annual Trupanion revenue exceeded $1 billion during his leadership.
- Received a 2015 EY Entrepreneur Of The Year Pacific Northwest award in financial services.

## Latest updates

- **2026-04** — Trupanion’s 2026 proxy identifies Rawlings as chair of the board and includes his board biography.
- **2024-08** — Margi Tooth succeeded Rawlings as CEO on August 1; he remained board chair.

## Links

- Website: https://www.trupanion.com/about/darryl-rawlings

---

Profile page: https://yespress.io/darryl-rawlings
Published by YesPress — https://yespress.io
Last updated: 2026-10-23