| Insider | Role | Shares | Value | Buys | Sells |
|---|---|---|---|---|---|
| Date | Ticker | Insider | Role | Type | Shares | Price | Value | Chg% | SEC |
|---|---|---|---|---|---|---|---|---|---|
| Insider | Role | Shares | Value | Buys | Sells |
|---|---|---|---|---|---|
| Date | Ticker | Insider | Role | Type | Shares | Price | Value | Chg% | SEC |
|---|---|---|---|---|---|---|---|---|---|
Director | Chief Executive Officer | CEO +1 more
1 company
Darryl Rawlings is Director at TRUP. Darryl Rawlings's net worth is not public. Form 4 filings only show shares in the companies where this person is an insider; those holdings are worth an estimated $825K at current prices.
Our model assigns Darryl Rawlings a strong insider score of 80/100, based on 51 past trades. Over a 12-month horizon, 96.1% of those trades were profitable, with an average 12-month return of +42.7%.
The TRUP filings lean toward selling, a net 438,898 shares.
Darryl Rawlings has 120 Form 4 filings on record from October 2019 to August 2026, all as Director at Trupanion (TRUP), 2019–2026.
The 306 reported transactions were 102 open-market sales, 95 option exercises, 65 tax withholdings and 32 gifts, plus smaller numbers of other types.
Counted by filing, the open-market trades come to 1 purchase worth about $500K and 80 sales worth about $33.6M.
The only open-market purchase was 20,700 shares of TRUP at an average $24.14 on May 7, 2024, about $500K. Twelve months later TRUP was up 75%.
The largest open-market sale was 97,118 shares of TRUP at an average $100.66 on February 24, 2021, about $9.8M.
3 of the 4 sales since April 2023 were made under a Rule 10b5-1 trading plan; the other was not.
| Date | Ticker | Role | Type | Shares | Price | Value | Chg% | 3M | 12M | SEC |
|---|---|---|---|---|---|---|---|---|---|---|
| Sep 4, 2025 | TRUP Trupanion, Inc. | Director | Sell | 50,000 | $44.73 | $2,236,725.75 | -3.4% | -18.8% | -37.7% | |
| May 7, 2024 | TRUP Trupanion, Inc. | Chief Executive Officer | Buy | 20,700 | $24.14 | $499,662.81 | +3.5% | +39.5% | +74.6% | |
| May 8, 2023 | TRUP Trupanion, Inc. | Chief Executive Officer | Sell10b5-1 | 4,000 | $25.30 | $101,188.00 | -0.5% | +23.8% | 0.0% | |
| Apr 19, 2023 | TRUP Trupanion, Inc. | Chief Executive Officer | Sell10b5-1 | 4,000 | $35.48 | $141,920.00 | -0.5% | -26.2% | -40.3% | |
| Apr 4, 2023 | TRUP Trupanion, Inc. | Chief Executive Officer | Sell10b5-1 | 4,000 | $41.20 | $164,810.00 | -0.5% | -49.1% | -35.7% | |
| Mar 16, 2023 | TRUP Trupanion, Inc. | Chief Executive Officer | Sell | 4,000 | $55.17 | $220,680.00 | -0.5% | -56.0% | -52.2% | |
| Feb 28, 2023 | TRUP Trupanion, Inc. | Chief Executive Officer | Sale+OE | 4,000 | $58.10 | $232,413.60 | -0.5% | -64.2% | -51.9% | |
| Feb 13, 2023 | TRUP Trupanion, Inc. | Chief Executive Officer | Sell | 4,000 | $58.50 | $234,014.00 | -0.5% | -65.5% | -47.9% | |
| Jan 26, 2023 | TRUP Trupanion, Inc. | Chief Executive Officer | Sell | 4,000 | $54.33 | $217,310.80 | -0.5% | -43.2% | -47.7% | |
| Jan 9, 2023 | TRUP Trupanion, Inc. | Chief Executive Officer | Sell | 4,000 | $48.54 | $194,172.00 | -0.5% | -12.1% | -41.0% |