InsiderTrades

RAWLINGS DARRYL

SEC CIK 1611679 · EDGAR

Buying vs selling by month open-market trades, last 60 months, TRUP
BoughtSold

Companies

TickerCompanyTitleHoldingBoughtSoldTradesFirstLast
TRUPTRUPANION, INC.Dir 25.2K $999.4K $15.17M 1252021-06-302026-08-22

Most active insiders at TRUP, 12 months

#InsiderTitleBoughtSold
1 Tooth MargaretCEO, Dir —$1.68M
2 Qureshi FawwadCFO —$734.3K
3 GALLAGHER JOHN RCOO —$621.8K
4 DREYER EMILYChief Revenue Off —$219.3K
5 WEINRAUCH STEVEEVP, North Am, Vet Strategy —$149.1K
6 MCGIBNEY BRENNAChief Administration Off ——
7 WHEELER SIMONEVP, Trupanion International ——
8 BEARMAN ASHERCLO ——
9 RUBIN HOWARD EDir ——
10 RAWLINGS DARRYLDir ——

Transactions 125

Type
Reset
X Filed Traded Ticker Company Insider Title Type Price Qty Owned ΔOwn Value
D 2026-08-26 18:56 2026-08-22 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx — +313 25.2K +1% —
D 2026-05-27 21:57 2026-05-22 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx — +312 24.8K +1% —
I 2026-05-08 21:41 2026-05-06 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir J - Other — +1,359 1.44M +0.1% —
D 2026-02-27 2026-02-25 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx — +946 42.2K +2% —
DM 2026-02-24 2026-02-22 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx — +6,563 35.0K +23% —
D 2025-11-26 2025-11-25 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx — +946 34.7K +3% —
DM 2025-11-25 2025-11-24 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx — +6,562 33.8K +24% —
D 2025-11-20 2025-11-20 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx $14.95 +2,000 27.2K +8% +$29.9K
MI 2025-09-05 2025-09-03+ TRUP TRUPANION, INC. RAWLINGS DARRYL Dir S - Sale $44.74 -50.0K 1.44M -3% -$2.24M
DM 2025-08-27 2025-05-22+ TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx — +15.0K 24.0K +168% —
DM 2025-02-27 2025-02-25 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx — +3,684 644.3K +0.6% —
DM 2025-02-27 2025-02-25 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir F - Tax $34.12 -896 644.4K -0.1% -$30.6K
DM 2025-02-26 2025-02-24 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir F - Tax $33.41 -2,098 641.6K -0.3% -$70.1K
DM 2025-02-26 2025-02-24 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx — +7,500 642.0K +1% —
DM 2024-11-27 2024-11-22+ TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx — +9,934 638.4K +2% —
DM 2024-11-27 2024-11-22+ TRUP TRUPANION, INC. RAWLINGS DARRYL Dir F - Tax $53.54 -3,626 630.4K -0.6% -$194.2K
DM 2024-08-27 2024-08-25 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx — +3,684 630.5K +0.6% —
DM 2024-08-27 2024-08-25 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir F - Tax $46.63 -896 627.8K -0.1% -$41.8K
D 2024-08-26 2024-08-22 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir F - Tax $45.39 -1,521 627.1K -0.2% -$69.0K
D 2024-08-26 2024-08-22 TRUP TRUPANION, INC. RAWLINGS DARRYL Dir M - OptEx — +6,250 628.6K +1% —
DM 2024-05-29 2024-05-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir F - Tax $28.95 -896 621.6K -0.1% -$25.9K
DM 2024-05-29 2024-05-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx — +3,682 622.6K +0.6% —
D 2024-05-24 2024-05-22 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir F - Tax $29.19 -1,522 619.6K -0.2% -$44.4K
D 2024-05-24 2024-05-22 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx — +6,250 621.1K +1% —
A 2024-05-15 2024-05-07 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir P - Purchase $24.14 +20.7K 614.8K +3% +$499.7K
2024-05-09 2024-05-07 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir P - Purchase $24.14 +20.7K 614.8K +3% +$499.7K
D 2024-02-29 2024-02-27 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir F - Tax $27.27 -188 594.1K -0.0% -$5,127
D 2024-02-29 2024-02-27 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx — +803 594.3K +0.1% —
DM 2024-02-27 2024-02-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx — +5,782 593.8K +1.0% —
DM 2024-02-27 2024-02-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir F - Tax $23.00 -1,713 593.5K -0.3% -$39.4K
DM 2023-11-28 2023-11-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir F - Tax $27.07 -1,523 588.7K -0.3% -$41.2K
DM 2023-11-28 2023-11-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx — +5,782 589.4K +1.0% —
DM 2023-08-29 2023-08-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir F - Tax $29.88 -1,406 584.5K -0.2% -$42.0K
DM 2023-08-29 2023-08-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx — +5,782 585.1K +1.0% —
DM 2023-05-30 2023-05-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx — +5,780 581.1K +1% —
DM 2023-05-30 2023-05-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir F - Tax $20.64 -1,406 580.1K -0.2% -$29.0K
I 2023-05-10 2023-05-08 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $25.30 -4,000 829.1K -0.5% -$101.2K
I 2023-04-20 2023-04-19 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $35.48 -4,000 833.1K -0.5% -$141.9K
I 2023-04-06 2023-04-04 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $41.20 -4,000 837.1K -0.5% -$164.8K
I 2023-03-20 2023-03-16 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $55.17 -4,000 841.1K -0.5% -$220.7K
DM 2023-02-28 2023-02-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx $0.00 +10.1K 570.4K +2% $0
DI 2023-02-28 2023-02-28 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale+OE $58.10 -4,000 845.1K -0.5% -$232.4K
DM 2023-02-28 2023-02-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir F - Tax $56.53 -2,564 569.9K -0.4% -$144.9K
I 2023-02-15 2023-02-13 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $58.50 -4,000 849.1K -0.5% -$234.0K
I 2023-01-30 2023-01-26 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $54.33 -4,000 853.1K -0.5% -$217.3K
I 2023-01-11 2023-01-09 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $48.54 -4,000 857.1K -0.5% -$194.2K
I 2022-12-28 2022-12-23 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $48.96 -4,000 861.1K -0.5% -$195.8K
I 2022-12-28 2022-12-20 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 +4,000 865.1K +0.5% $0
2022-12-28 2022-12-20 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 -4,000 568.9K -0.7% $0
D 2022-12-19 2022-12-15 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx $17.97 +4,000 572.9K +0.7% +$71.9K
I 2022-12-09 2022-12-07 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $51.03 -4,000 861.1K -0.5% -$204.1K
DM 2022-11-29 2022-11-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx — +6,340 566.5K +1% —
DM 2022-11-29 2022-11-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir F - Tax $54.13 -2,494 568.9K -0.4% -$135.0K
I 2022-11-22 2022-11-18 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $60.41 -4,000 865.1K -0.5% -$241.6K
2022-11-22 2022-11-14 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 -12.0K 565.0K -2% $0
I 2022-11-22 2022-11-14 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 +12.0K 869.1K +1% $0
D 2022-11-10 2022-11-09 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx $17.97 +12.0K 577.0K +2% +$215.6K
2022-11-07 2022-11-01 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 -4,000 565.0K -0.7% $0
I 2022-11-07 2022-11-01 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 +4,000 861.1K +0.5% $0
I 2022-11-07 2022-11-03 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $44.16 -4,000 857.1K -0.5% -$176.6K
D 2022-10-27 2022-10-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx $17.97 +4,000 569.0K +0.7% +$71.9K
AI 2022-10-19 2022-09-30 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $61.38 -4,000 857.1K -0.5% -$245.5K
A 2022-10-19 2022-09-28 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 -4,000 565.0K -0.7% $0
AI 2022-10-19 2022-09-28 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 +4,000 861.1K +0.5% $0
AI 2022-10-19 2022-08-08 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 +12.0K 869.1K +1% $0
A 2022-10-19 2022-08-08 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 -12.0K 561.2K -2% $0
AI 2022-10-19 2022-08-10 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $66.86 -4,000 865.1K -0.5% -$267.4K
I 2022-10-19 2022-10-17 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $53.94 -4,000 857.1K -0.5% -$215.8K
I 2022-10-19 2022-10-12 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 +4,000 861.1K +0.5% $0
2022-10-19 2022-10-12 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 -4,000 565.0K -0.7% $0
D 2022-10-11 2022-10-07 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx $14.95 +4,000 569.0K +0.7% +$59.8K
I 2022-10-03 2022-09-30 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $61.38 -4,000 857.1K -0.5% -$245.5K
I 2022-10-03 2022-09-28 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 +4,000 861.1K +0.5% $0
2022-10-03 2022-09-28 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 -4,000 565.0K -0.7% $0
D 2022-09-26 2022-09-22 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx $14.95 +4,000 569.0K +0.7% +$59.8K
I 2022-09-16 2022-09-14 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $65.57 -4,000 857.1K -0.5% -$262.3K
DMA 2022-09-02 2022-08-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx — +6,341 562.7K +1% —
DMA 2022-09-02 2022-08-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir F - Tax $77.49 -2,494 565.0K -0.4% -$193.3K
I 2022-09-01 2022-08-29 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $69.34 -4,000 861.1K -0.5% -$277.4K
DM 2022-08-29 2022-08-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir F - Tax $77.49 -1,704 562.3K -0.3% -$132.0K
DM 2022-08-29 2022-08-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx — +6,341 562.7K +1% —
I 2022-08-11 2022-08-08 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $66.86 -4,000 865.1K -0.5% -$267.4K
I 2022-08-11 2022-08-08 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 +12.0K 869.1K +1% $0
2022-08-11 2022-08-08 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 -12.0K 561.2K -2% $0
D 2022-08-03 2022-08-01 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx $14.95 +12.0K 573.2K +2% +$179.4K
I 2022-07-28 2022-07-26 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $64.21 -4,000 857.1K -0.5% -$256.8K
I 2022-07-11 2022-07-07 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $66.11 -4,000 861.1K -0.5% -$264.4K
I 2022-06-24 2022-06-21 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $53.10 -4,000 865.1K -0.5% -$212.4K
I 2022-06-06 2022-06-02 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $66.52 -4,000 869.1K -0.5% -$266.1K
DI 2022-05-27 2022-05-26 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 +16.0K 873.1K +2% $0
D 2022-05-27 2022-05-26 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 -16.0K 561.2K -3% $0
DM 2022-05-27 2022-05-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir F - Tax $63.20 -2,494 574.3K -0.4% -$157.6K
DM 2022-05-27 2022-05-25 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx — +6,340 574.9K +1% —
I 2022-05-19 2022-05-17 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $64.90 -4,000 857.1K -0.5% -$259.6K
DM 2022-05-17 2022-05-04+ TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir M - OptEx $14.95 +20.0K 573.4K +4% +$299.0K
D 2022-05-17 2022-05-11 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 -4,000 557.4K -0.7% $0
DI 2022-05-17 2022-05-11 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 +4,000 861.1K +0.5% $0
M 2022-05-03 2022-04-22+ TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 -8,000 557.4K -1% $0
MI 2022-05-03 2022-04-22+ TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir G - Gift $0.00 +8,000 861.1K +0.9% $0
I 2022-05-03 2022-04-29 TRUP TRUPANION, INC. RAWLINGS DARRYL CEO, Dir S - Sale $70.37 -4,000 857.1K -0.5% -$281.5K

Purchase Sale Sale after option exercise All abbreviations