Darryl Rawlings

Companies

• TrupanionBoard member Jul 17, 2014 to now¹
• TrupanionChief executive officer Jul 17, 2014 to May 29, 2024¹
• TrupanionPresident Jul 17, 2014 to Feb 17, 2021¹

Holdings

Stock this person has reported owning, from the forms officers and directors file with the SEC. See the biggest insider stakes.

Shares held

• TTrupanion TRUP1,460,491 shares²$40.6M at $27.80Aug 22, 2026

As of each latest filing. The line shows shares held over time.

Recent filings

• Aug 22, 2026Exercised options 313 shares of Trupanion²
• May 22, 2026Exercised options 312 shares of Trupanion³
• May 6, 2026Other 1,359 shares of Trupanion⁴
• Feb 25, 2026Exercised options 946 shares of Trupanion⁵
• Feb 22, 2026Exercised options 6,250 shares of Trupanion⁶
• Feb 22, 2026Exercised options 313 shares of Trupanion⁶
• Nov 25, 2025Exercised options 946 shares of Trupanion⁷
• Nov 24, 2025Exercised options 6,250 shares of Trupanion⁸
• Nov 24, 2025Exercised options 312 shares of Trupanion⁸
• Nov 20, 2025Exercised options 2,000 shares at $14.95 of Trupanion⁹
• Sep 4, 2025Sold 30,369 shares at $44.70 of Trupanion¹⁰
• Sep 3, 2025Sold 19,631 shares at $44.79 of Trupanion¹⁰
• Aug 25, 2025Exercised options 946 shares of Trupanion¹¹
• Aug 22, 2025Exercised options 313 shares of Trupanion¹¹
• Aug 22, 2025Exercised options 6,250 shares of Trupanion¹¹
• May 22, 2025Exercised options 945 shares of Trupanion¹¹
• May 22, 2025Exercised options 312 shares of Trupanion¹¹
• May 22, 2025Exercised options 6,250 shares of Trupanion¹¹
• Feb 25, 2025Shares withheld for tax 230 shares at $34.12 of Trupanion¹²
• Feb 25, 2025Exercised options 946 shares of Trupanion¹²
• Feb 25, 2025Shares withheld for tax 666 shares at $34.12 of Trupanion¹²
• Feb 25, 2025Exercised options 2,738 shares of Trupanion¹²
• Feb 24, 2025Shares withheld for tax 370 shares at $33.41 of Trupanion¹³
• Feb 24, 2025Exercised options 1,250 shares of Trupanion¹³
• Feb 24, 2025Shares withheld for tax 1,728 shares at $33.41 of Trupanion¹³