Darryl Rawlings

Darryl Rawlings

Net worth: 32 M $ as of 2026-05-30

56 year
Finance
Process Industries
Consumer Services

Profile

Founder of Trupanion, Inc., North American Pet Health Insurance Association, Canadian Cigar Co. Ltd. and Canada Pet Health Insurance Services, Inc., Darryl Rawlings is an entrepreneur and businessperson who has been at the helm of 7 different companies and currently is Chairman at Naked Wines Plc and Chief Executive Officer & Director at Trupanion, Inc., Chief Executive Officer for Trupanion Managers USA, Inc., Chief Executive Officer & Director at Canada Pet Health Insurance Services, Inc., Chief Executive Officer at American Pet Insurance Co. and Chief Executive Officer at American Pet Insurance Co. (Investment Portfolio) (which are all subsidiaries of Trupanion, Inc.). Darryl Rawlings is also on the board of Seattle Academy of Arts & Science and Gallant Pet, Inc. and Member of North American Pet Health Insurance Association. In the past he held the position of Director-Sales & Marketing of Telos Corp., Director-Sales & Marketing for Cycomm International, Inc. and President & Chief Executive Officer at Vetinsurance International, Inc.

Known holdings in public companies

CompanyDateNumber of sharesValuationValuation date
2026-05-21 1,457,184 ( 3.34% ) 32 M $ 2026-05-30

Darryl Rawlings active positions

CompaniesPositionStart
TRUPANION, INC. Founder 1999-12-31
Founder 2011-04-12
Chief Executive Officer -
Chief Executive Officer -
Chief Executive Officer -
North American Pet Health Insurance Association
Founder -
Director/Board Member -
Director/Board Member -

Former positions of Darryl Rawlings

CompaniesPositionEnd
NAKED WINES PLC Chairman 2022-10-19
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See the detail of Darryl Rawlings's experience

Training of Darryl Rawlings

Experiences
Positions held

Active

Inactive

Listed companies

Private companies

Connections

28

1st degree connections

14

1st degree companies

Male

Female

Members of the board

Executives

Linked companies

Private companies14

Technology Services

Electronic Technology

Process Industries

Consumer Non-Durables

Consumer Services

Consumer Services

Finance

North American Pet Health Insurance Association

Canadian Cigar Co. Ltd.

Finance

Process Industries

Finance

Finance

Health Technology

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