12 insiders reported 550 Form 4 transactions for TRUPANION, INC. (TRUP) over the past 18 months (most recent 2026-09-15). Recent activity: Tooth Margaret (CEO) Sell 1,000 shares, GALLAGHER JOHN R (Chief Operating Officer) Sell 3,604 shares, RUBIN HOWARD E (Director) Buy 140 shares, RAWLINGS DARRYL (Director) Buy 313 shares, RUBIN HOWARD E (Director) Buy 140 shares. Source: SEC Form 4.
| Date | Insider | Title | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-09-15 | Tooth Margaret | CEO | Sell | 1,000 | $25,000 |
| 2026-09-01 | GALLAGHER JOHN R | Chief Operating Officer | Sell | 3,604 | $107,039 |
| 2026-08-26 | RUBIN HOWARD E | Director | Buy | 140 | $0 |
| 2026-08-26 | RAWLINGS DARRYL | Director | Buy | 313 | $0 |
| 2026-08-26 | RUBIN HOWARD E | Director | Buy | 140 | $0 |
| 2026-08-26 | BEARMAN ASHER | Chief Legal Officer | Buy | 265 | $0 |
| 2026-08-26 | Tooth Margaret | CEO | Buy | 313 | $0 |
| 2026-08-26 | WHEELER SIMON | EVP, Trupanion International | Buy | 528 | $0 |
| 2026-08-26 | MCGIBNEY BRENNA | Chief Administration Officer | Buy | 1,250 | $0 |
| 2026-08-26 | GALLAGHER JOHN R | Chief Operating Officer | Buy | 865 | $0 |
| 2026-08-26 | WEINRAUCH STEVE | EVP, North Am & Vet Strategy | Buy | 2,931 | $0 |
| 2026-08-26 | Qureshi Fawwad | Chief Financial Officer | Buy | 313 | $0 |
| 2026-08-26 | POWELL BRADLEY S | Director | Buy | 1,640 | $0 |
| 2026-08-26 | BEARMAN ASHER | Chief Legal Officer | Sell | 86 | $2,731 |
| 2026-08-26 | Tooth Margaret | CEO | Sell | 123 | $3,906 |
| 2026-08-26 | WHEELER SIMON | EVP, Trupanion International | Sell | 263 | $8,353 |
| 2026-08-26 | MCGIBNEY BRENNA | Chief Administration Officer | Sell | 669 | $21,247 |
| 2026-08-26 | GALLAGHER JOHN R | Chief Operating Officer | Sell | 210 | $6,670 |
| 2026-08-26 | WEINRAUCH STEVE | EVP, North Am & Vet Strategy | Sell | 713 | $22,645 |
| 2026-08-26 | Qureshi Fawwad | Chief Financial Officer | Sell | 124 | $3,938 |
| 2026-08-26 | RUBIN HOWARD E | Director | Buy | 140 | $0 |
| 2026-08-26 | BEARMAN ASHER | Chief Legal Officer | Buy | 9 | $0 |
| 2026-08-26 | Tooth Margaret | CEO | Buy | 3,042 | $0 |
| 2026-08-26 | WHEELER SIMON | EVP, Trupanion International | Buy | 385 | $0 |
| 2026-08-26 | MCGIBNEY BRENNA | Chief Administration Officer | Buy | 1,881 | $0 |
Source: SEC Form 4 filings · as of 2026-09-15