Darryl Rawlings is the CEO and Chair of Trupanion, a company dedicated to pet insurance, known for its strong growth in recent years. Born on July 15, 1973, he holds a degree in business administration. Rawlings co-founded Trupanion and has...

Darryl Rawlings is the CEO and Chair of Trupanion, a company dedicated to pet insurance, known for its strong growth in recent years. Born on July 15, 1973, he holds a degree in business administration. Rawlings co-founded Trupanion and has been leading it since 2000. Notably, under his leadership, the company's intrinsic value per share saw impressive growth of 31.4% in 2020, highlighting his effectiveness in steering the company forward. In 2022, he opted not to take his bonus, which demonstrated his commitment to long-term performance rather than short-term gains. His insider trading activity has shown substantial fluctuations, with notable stock holdings reaching a peak of $152.77 million in January 2021. Recently, he announced his resignation as CEO effective August 2024 but will remain active as a director and Chair of the Board, signaling a smooth transition within the company. His focus includes enhancing pet care and supporting responsible pet ownership, tying back to the mission of Trupanion, which values helping loving pet owners budget for their furry friends.

Quick Links

1. Rivals

2. Holdings

3. Insider Trading

4. Compensation History

5. Other Trupanion CEOs

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Darryl Rawlings

Ex-CEO of Trupanion

Education

Bachelor's degree in business administration

Field of Expertise

Business & Management

Sector of Economy

Financial Services

Born

July 15, 1973 - 51 years ago

CEO of Trupanion for

10 years 7 months (Jan 2014 - Aug 2024)

Previous Experience

CEO of Trupanion, Inc. since 2014; previously held various leadership roles in the pet insurance industry.

Rivals

Competitors/colleagues of Darryl Rawlings

Holdings

See how much did Darryl Rawlings make over time.

Darryl Rawlings has had notable fluctuations in his stock holdings with Trupanion. At one point in January 2021, his holdings peaked at an impressive $152.77 million. Since then, he has experienced various ups and downs, reflecting the company's stock performance....

Darryl Rawlings has had notable fluctuations in his stock holdings with Trupanion. At one point in January 2021, his holdings peaked at an impressive $152.77 million. Since then, he has experienced various ups and downs, reflecting the company's stock performance. His holdings dipped to around $32.81 million by October 2019, but he rebounded to a significant holding of $147.86 million by December 2020. In recent months, his holdings continue to reflect substantial value, hovering around $71.58 million, indicating a strong commitment to his company's future even as he prepares for leadership changes.

Mar 11, 2025

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shares

TRUP @ $33.02

Total Stock Sold

$45.37M

TRUP

$45.37M

989,778 TRUP shares

What if they kept their stock?

If Darryl Rawlings didn't sell their stock, today they would have:
Extra TRUP989,778 shares worth $34.90M.
This is -23.08% and $10.47M less than what they got when they sold the stock.

Charitable Transactions

TRUP

1,300,147 shares

TRUP

Recent Charitable Transactions

TRUP

4,000 shares

TRUP

Dec 23, 2022

Charity

TRUP

12,000 shares

TRUP

Nov 18, 2022

Charity

TRUP

4,000 shares

TRUP

Nov 3, 2022

Charity

TRUP

4,000 shares

TRUP

Oct 17, 2022

Charity

TRUP

4,000 shares

TRUP

Sep 28, 2022

Charity

TRUP

4,000 shares

TRUP

Sep 30, 2022

Charity

Insider Trading

See recent insider trades of Darryl Rawlings.

TRUP

$499.66K

TRUP at $24.14/share

May 7, 2024

Purchase

TRUP

$499.66K

TRUP at $24.14/share

May 7, 2024

Purchase

TRUP

$101.19K

TRUP at $25.30/share

May 8, 2023

Sale

TRUP

$141.92K

TRUP at $35.48/share

Apr 19, 2023

Sale

TRUP

$164.81K

TRUP at $41.20/share

Apr 4, 2023

Sale

TRUP

$220.68K

TRUP at $55.17/share

Mar 16, 2023

Sale

TRUP

$232.41K

TRUP at $58.10/share

Feb 25, 2023

Sale

TRUP

$234.01K

TRUP at $58.50/share

Feb 13, 2023

Sale

TRUP

$217.31K

TRUP at $54.33/share

Jan 26, 2023

Sale

TRUP

$194.17K

TRUP at $48.54/share

Jan 9, 2023

Sale

Compensation History

See how much did Darryl Rawlings make over time.

In 2022, Darryl Rawlings received a total compensation of $300,000, all of which came as a salary. He waived his short-term incentive bonus of $21,534 that year, showing he prioritized long-term growth over immediate financial rewards. This kind of decision aligns with his history of waiving bonuses during challenging times. In 2020, his total compensation was valued at over $1.16 million, including bonuses and stock awards, reflecting the company's performance goals. Despite fluctuations, his focus is on creating value for shareholders rather than maximizing his immediate pay.

Year

2022

Total Compensation

$300.00K

Salary

$300.00K

Board Justification

The compensation philosophy aims to align team member incentives with long-term stockholder interests, focusing on performance-based pay and equity ownership.

Bonus

$0.00

Board Justification

Mr. Rawlings waived receipt of his earned short-term incentive award for performance year 2022, which was $21,534.

Other

$0.00

Board Justification

No additional compensation was reported outside of salary, bonus, and stock awards.

Restricted Stock

$0.00(0 RSU)

Board Justification

No long-term incentive awards were issued to employees for performance year 2022 due to insufficient intrinsic value growth.

Performance Metrics

The primary performance metric for determining compensation is the growth of intrinsic value per share.

Other Trupanion CEOs

Here are other CEOs of Trupanion

Margaret Tooth

CEO of Trupanion

August 2024 - Present