As of April 22, 2026, the three largest insider holders of TRUP are Darryl Rawlings (Chief Executive Officer, 1.41Mn shares), Howard E Rubin (Director, 232.55K shares), Margaret Tooth (Ceo, 164.83K shares).
| Holder | Position | Shares (Direct) | Shares (Indirect) | Report Date |
|---|---|---|---|---|
| Darryl Rawlings | Chief Executive Officer | 0 | 1,413,281 | 05 Sep, 2025 |
| Howard E Rubin | - | 232,550 | 0 | 24 Feb, 2026 |
| Margaret Tooth | Ceo | 164,829 | 0 | 27 Feb, 2026 |
| Murray B Low | - | 154,534 | 0 | 12 Jan, 2026 |
| Dan Levitan | - | 95,116 | 0 | 03 Apr, 2024 |
| Steve Weinrauch | Evp, North Am Vet Strategy | 72,559 | 0 | 27 Feb, 2026 |
| Asher Bearman | Chief Legal Officer | 70,479 | 0 | 27 Feb, 2026 |
| Darryl Rawlings | Chief Executive Officer | 42,232 | 0 | 27 Feb, 2026 |
| Tricia Plouf | Evp, Pricing | 41,023 | 0 | 10 Feb, 2023 |
| Emily Dreyer | Chief Revenue Officer | 35,627 | 0 | 06 Mar, 2026 |
| John R Gallagher | Chief Operating Officer | 31,957 | 0 | 01 Apr, 2026 |
| Simon Wheeler | Evp, Trupanion International | 23,087 | 0 | 27 Feb, 2026 |
| Jacqueline L Davidson | - | 14,456 | 0 | 01 Jul, 2024 |
| Melissa Joy Hewitt | General Manager | 9,779 | 0 | 27 Feb, 2025 |
| Gavin Friedman | Evp, Legal And Regulatory | 9,591 | 0 | 03 Feb, 2023 |
| Brenna Mcgibney | Chief Administration Officer | 8,453 | 0 | 27 Feb, 2026 |
| Christopher J Kearns | Chief Legal Officer | 8,159 | 0 | 26 Feb, 2025 |
| Andrew D. Wolff | Chief Financial Officer | 7,895 | 0 | 30 May, 2023 |
| Elizabeth Mclaughlin | - | 7,472 | 0 | 01 Jul, 2024 |
| Paulette R. Dodson | - | 6,418 | 0 | 01 Jul, 2024 |
| Michael Doak | - | 5,866 | 0 | 01 Sep, 2023 |
| Max Broden | - | 5,408 | 0 | 01 Jul, 2024 |
| Wei Li | Interim Cfo | 4,909 | 0 | 29 Aug, 2023 |
| Zay Satchu | - | 4,788 | 0 | 03 Apr, 2024 |
| Jason Wasdin | General Manager | 4,553 | 0 | 27 Feb, 2025 |
| Travis Worra | General Manager | 4,179 | 0 | 27 Nov, 2024 |
| Kalpesh Raval | General Manager | 3,886 | 0 | 27 Nov, 2024 |
| Eric L Johnson | - | 2,691 | 0 | 04 Jan, 2023 |
| Bradley S Powell | - | 1,267 | 0 | 24 Feb, 2026 |
| Richard Enthoven | - | 485 | 0 | 03 Jan, 2024 |
* Please note that the shares above only reflect shares from the fund portfolio and the institutional portfolio. Shares from the personal portfolio are excluded from this Institutional Ownership Page. See these insiders' latest transactions here on Insider Page.
| Transaction Date | Insider Name | Security Class | Transaction Type | Shares Traded | Price | Shares Remaining | Ownership | Code |
|---|---|---|---|---|---|---|---|---|
| 30 Mar, 2026 | John R Gallagher | Common Stock | D | 430 | $25.47 | 31,957 | D | S |
| 04 Mar, 2026 | Emily Dreyer | Common Stock | D | 7,792 | $28.15 | 35,627 | D | S |
| 27 Feb, 2026 | John R Gallagher | Common Stock | D | 5,283 | $26.52 | 32,387 | D | S |
| 27 Feb, 2026 | Fawwad Qureshi | Common Stock | D | 2,837 | $26.46 | 0 | D | S |
| 25 Feb, 2026 | Steve Weinrauch | Common Stock | A | 531 | - | 72,388 | D | M |
| 25 Feb, 2026 | Simon Wheeler | Common Stock | A | 322 | - | 23,238 | D | M |
| 25 Feb, 2026 | Brenna Mcgibney | Common Stock | A | 233 | - | 8,383 | D | M |
| 25 Feb, 2026 | Emily Dreyer | Common Stock | A | 1,482 | - | 43,519 | D | M |
| 25 Feb, 2026 | John R Gallagher | Common Stock | A | 735 | - | 37,449 | D | M |
| 25 Feb, 2026 | Asher Bearman | Common Stock | A | 180 | - | 70,470 | D | M |
| 25 Feb, 2026 | Darryl Rawlings | Common Stock | A | 946 | - | 42,232 | D | M |
| 25 Feb, 2026 | Margaret Tooth | Common Stock | A | 3,266 | - | 165,355 | D | M |
| 25 Feb, 2026 | Fawwad Qureshi | Common Stock | D | 4,645 | $25.61 | 0 | D | S |
| 25 Feb, 2026 | Simon Wheeler | Common Stock | D | 151 | $26.70 | 23,087 | D | F |
| 25 Feb, 2026 | Margaret Tooth | Common Stock | D | 1,285 | $26.70 | 164,070 | D | F |
| 25 Feb, 2026 | Steve Weinrauch | Common Stock | D | 129 | $26.70 | 72,259 | D | F |
| 25 Feb, 2026 | Asher Bearman | Common Stock | D | 68 | $26.70 | 70,402 | D | F |
| 25 Feb, 2026 | Brenna Mcgibney | Common Stock | D | 124 | $26.70 | 8,259 | D | F |
| 25 Feb, 2026 | Emily Dreyer | Common Stock | D | 360 | $26.70 | 43,159 | D | F |
| 25 Feb, 2026 | Darryl Rawlings | Restricted Stock Unit (RSU) | D | 946 | $0.00 | 0 | D | M |