As of September 29, 2026, Trupanion's top three insider holders are Darryl Rawlings (Chief Executive Officer, 1.44Mn shares), Howard E Rubin (Director, 233.29K shares), Margaret Tooth (Ceo, 185.95K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Howard E Rubin | Director | 233,288 | 0 | 233,288 | 21.0% | 26 Aug, 2026 |
| 2 | Margaret Tooth | Ceo | 185,952 | 0 | 185,952 | 16.8% | 14 Sep, 2026 |
| 3 | Murray B Low | Director | 154,534 | 0 | 154,534 | 13.9% | 12 Jan, 2026 |
| 4 | Dan Levitan | Director | 95,116 | 0 | 95,116 | 8.6% | 03 Apr, 2024 |
| 5 | Steve Weinrauch | Evp, North Am Vet Strategy | 81,740 | 0 | 81,740 | 7.4% | 26 Aug, 2026 |
| 6 | Asher Bearman | Chief Legal Officer | 74,013 | 0 | 74,013 | 6.7% | 26 Aug, 2026 |
| 7 | Tricia Plouf | Evp, Pricing | 41,023 | 0 | 41,023 | 3.7% | 10 Feb, 2023 |
| 8 | Emily Dreyer | Chief Revenue Officer | 35,627 | 0 | 35,627 | 3.2% | 06 Mar, 2026 |
| 9 | John R Gallagher | Chief Operating Officer | 33,742 | 0 | 33,742 | 3.0% | 01 Sep, 2026 |
| 10 | Simon Wheeler | Evp, Trupanion International | 25,327 | 0 | 25,327 | 2.3% | 26 Aug, 2026 |
| 11 | Darryl Rawlings | Chief Executive Officer | 25,151 | 0 | 25,151 | 2.3% | 26 Aug, 2026 |
| 12 | Jacqueline L Davidson | Director | 14,456 | 0 | 14,456 | 1.3% | 01 Jul, 2024 |
| 13 | Brenna Mcgibney | Chief Administration Officer | 14,437 | 0 | 14,437 | 1.3% | 26 Aug, 2026 |
| 14 | Melissa Joy Hewitt | General Manager | 9,779 | 0 | 9,779 | 0.9% | 27 Feb, 2025 |
| 15 | Gavin Friedman | Evp, Legal And Regulatory | 9,591 | 0 | 9,591 | 0.9% | 03 Feb, 2023 |
| 16 | Christopher J Kearns | Chief Legal Officer | 8,159 | 0 | 8,159 | 0.7% | 26 Feb, 2025 |
| 17 | Andrew D. Wolff | Chief Financial Officer | 7,895 | 0 | 7,895 | 0.7% | 30 May, 2023 |
| 18 | Elizabeth Mclaughlin | Director | 7,472 | 0 | 7,472 | 0.7% | 01 Jul, 2024 |
| 19 | Paulette R. Dodson | Director | 6,418 | 0 | 6,418 | 0.6% | 01 Jul, 2024 |
| 20 | Michael Doak | Director | 5,866 | 0 | 5,866 | 0.5% | 01 Sep, 2023 |
| 21 | Max Broden | Director | 5,408 | 0 | 5,408 | 0.5% | 01 Jul, 2024 |
| 22 | Wei Li | Interim Cfo | 4,909 | 0 | 4,909 | 0.4% | 29 Aug, 2023 |
| 23 | Zay Satchu | Director | 4,788 | 0 | 4,788 | 0.4% | 03 Apr, 2024 |
| 24 | Jason Wasdin | General Manager | 4,553 | 0 | 4,553 | 0.4% | 27 Feb, 2025 |
| 25 | Fawwad Qureshi | Chief Financial Officer | 4,230 | 0 | 4,230 | 0.4% | 26 Aug, 2026 |
| 26 | Travis Worra | General Manager | 4,179 | 0 | 4,179 | 0.4% | 27 Nov, 2024 |
| 27 | Kalpesh Raval | General Manager | 3,886 | 0 | 3,886 | 0.4% | 27 Nov, 2024 |
| 28 | Bradley S Powell | Director | 3,546 | 0 | 3,546 | 0.3% | 26 Aug, 2026 |
| 29 | Eric L Johnson | Director | 2,691 | 0 | 2,691 | 0.2% | 04 Jan, 2023 |
| 30 | Richard Enthoven | Director | 485 | 0 | 485 | 0.0% | 03 Jan, 2024 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 28 Aug, 2026 | John R Gallagher | Chief Operating Officer | Disposed S | 3,604 | $29.70 | $107.04K | 33,742 | Direct |
| 22 Aug, 2026 | John R Gallagher | Chief Operating Officer | Acquired M | 865 | — | — | 33,068 | Direct |
| 22 Aug, 2026 | Simon Wheeler | Evp, Trupanion International | Acquired M | 528 | — | — | 24,767 | Direct |
| 22 Aug, 2026 | Darryl Rawlings | Director | Acquired M | 313 | — | — | 25,151 | Direct |
| 22 Aug, 2026 | Bradley S Powell | Director | Acquired M | 1,640 | — | — | 3,546 | Direct |
| 22 Aug, 2026 | Howard E Rubin | Director | Acquired M | 140 | — | — | 233,008 | Direct |
| 22 Aug, 2026 | Fawwad Qureshi | Chief Financial Officer | Acquired M | 313 | — | — | 2,394 | Direct |
| 22 Aug, 2026 | Steve Weinrauch | Evp, North Am Vet Strategy | Acquired M | 2,931 | — | — | 80,993 | Direct |
| 22 Aug, 2026 | Margaret Tooth | Ceo | Acquired M | 313 | — | — | 175,714 | Direct |
| 22 Aug, 2026 | Asher Bearman | Chief Legal Officer | Acquired M | 265 | — | — | 72,509 | Direct |
| 22 Aug, 2026 | Brenna Mcgibney | Chief Administration Officer | Acquired M | 1,250 | — | — | 12,695 | Direct |
| 22 Aug, 2026 | John R Gallagher | Chief Operating Officer | Disposed F | 210 | $31.76 | $6.67K | 32,858 | Direct |
| 22 Aug, 2026 | Darryl Rawlings | Director | Disposed M | 313 | $0.00 | $0 | 1,875 | Direct |
| 22 Aug, 2026 | Howard E Rubin | Director | Acquired M | 140 | — | — | 233,148 | Direct |
| 22 Aug, 2026 | Steve Weinrauch | Evp, North Am Vet Strategy | Disposed F | 713 | $31.76 | $22.64K | 80,280 | Direct |
| 22 Aug, 2026 | Fawwad Qureshi | Chief Financial Officer | Disposed F | 124 | $31.76 | $3.94K | 2,270 | Direct |
| 22 Aug, 2026 | Brenna Mcgibney | Chief Administration Officer | Disposed F | 669 | $31.76 | $21.25K | 12,026 | Direct |
| 22 Aug, 2026 | Margaret Tooth | Ceo | Disposed F | 123 | $31.76 | $3.91K | 175,591 | Direct |
| 22 Aug, 2026 | Asher Bearman | Chief Legal Officer | Disposed F | 86 | $31.76 | $2.73K | 72,423 | Direct |
| 22 Aug, 2026 | Simon Wheeler | Evp, Trupanion International | Disposed F | 263 | $31.76 | $8.35K | 24,504 | Direct |