Trupanion (TRUP) CEO exercises RSUs and sells 491 shares
Rhea-AI Filing Summary
Trupanion, Inc. CEO Margaret Tooth reported a mix of stock transactions including a small open‑market sale and multiple RSU conversions. On May 25, 2026 she sold 491 shares of common stock in an open‑market transaction at $21.86 per share and held 176,379 shares afterward. On May 22–25, 2026 she exercised and converted a total of 19,042 restricted stock units into common stock at a $0.00 exercise price, while 6,999 shares were withheld by the company to cover tax obligations, which the filing states do not represent sales by her. The report also notes an administrative correction adjusting previously disclosed beneficial ownership to reflect her current holdings as of the transaction dates.
Positive
- None.
Negative
- None.
Insider Trade Summary
Exercise and sale activity reported; no spread calculated
Exercise and Sale
15 txns
Insider
Tooth Margaret
Role
CEO
Sold
491 shs ($11K)
Approx. gross sale proceeds
$11K
Approx. exercise cost
$0.00
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Restricted Stock Unit (RSU) | 1,250 | $0.00 | $0.00 |
| Exercise | Common Stock | 1,250 | $0.00 | $0.00 |
| Sale | Common Stock | 491 | $21.86 | $11K |
| Exercise | Restricted Stock Unit (RSU) | 312 | $0.00 | $0.00 |
| Exercise | Restricted Stock Unit (RSU) | 3,043 | $0.00 | $0.00 |
| Exercise | Restricted Stock Unit (RSU) | 6,250 | $0.00 | $0.00 |
| Exercise | Restricted Stock Unit (RSU) | 8,187 | $0.00 | $0.00 |
| Exercise | Common Stock | 312 | $0.00 | $0.00 |
| Exercise Price or Tax Liability | Common Stock | 122 | $21.98 | $3K |
| Exercise | Common Stock | 3,043 | $0.00 | $0.00 |
| Exercise Price or Tax Liability | Common Stock | 1,197 | $21.98 | $26K |
| Exercise | Common Stock | 6,250 | $0.00 | $0.00 |
| Exercise Price or Tax Liability | Common Stock | 2,459 | $21.98 | $54K |
| Exercise | Common Stock | 8,187 | $0.00 | $0.00 |
| Exercise Price or Tax Liability | Common Stock | 3,221 | $21.98 | $71K |
Holdings After Transaction:
Restricted Stock Unit (RSU) — 111,880 shares (Direct);
Common Stock — 176,379 shares (Direct)
Footnotes (8)
- F1. Restricted stock units convert into common stock on a one-for-one basis.
- F2. This footnote corrects an administrative error in the reporting of previously disclosed holdings. The total number of securities beneficially owned and as reported in Table I has been adjusted accordingly to reflect the reporting person's current beneficial ownership as of the transaction date.
- F3. This Form 4 discloses the shares of common stock that have been withheld by the issuer to satisfy its income tax withholding and remittance obligations in connection with the vesting of the restricted stock units, and does not represent a sale by the reporting person.
- F4. On February 27, 2024, the reporting person was granted 5,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
- F5. On August 19, 2024, the reporting person was granted 48,679 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on August 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
- F6. On February 27, 2025, the reporting person was granted 50,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/8th of the total shares on May 22, 2025, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date.
- F7. On February 20, 2026, the reporting person was granted 65,497 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/8th of the total shares on May 22, 2026, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date.
- F8. On August 14, 2023, the reporting person was granted 20,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on August 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
Key Figures
Open-market sale: 491 shares at $21.86
Post-transaction holdings: 176,379 shares
RSUs converted: 19,042 shares
+3 more
6 metrics
Open-market sale
491 shares at $21.86
Common stock sale on May 25, 2026
Post-transaction holdings
176,379 shares
Common stock held directly after May 25, 2026
RSUs converted
19,042 shares
Restricted stock units converting into common stock May 22–25, 2026
Tax-withholding shares
6,999 shares at $21.98
Shares withheld by issuer for tax obligations on May 22, 2026
Largest RSU grant noted
65,497 RSUs
Grant dated February 20, 2026 with 1/8 initial vesting on May 22, 2026
Earlier RSU grant
50,000 RSUs
Grant dated February 27, 2025, vesting 1/8 on May 22, 2025 then quarterly
Key Terms
Restricted stock units (RSUs), tax-withholding disposition, derivative security, beneficially owned, +1 more
5 terms
Restricted stock units (RSUs) financial
"On February 27, 2025, the reporting person was granted 50,000 restricted stock units (RSUs)."
Restricted stock units (RSUs) are a type of company promise to give employees shares of stock in the future, usually after certain conditions like working for a set time. They are like a gift promised today that you receive later, which can become valuable if the company's stock price goes up. RSUs matter because they are a way companies reward employees and can be a significant part of compensation.
tax-withholding disposition financial
"Payment of exercise price or tax liability by delivering securities."
A tax-withholding disposition is an event or transaction—such as selling or transferring securities, exercising options, or receiving compensation—that triggers a requirement to hold back part of the payment and remit it to tax authorities. It matters to investors because it reduces the cash they receive immediately and can change the timing and amount of taxable income, like a cashier taking a portion of your sale proceeds to pay taxes before you get the rest.
derivative security financial
"Exercise or conversion of derivative security."
A derivative security is a financial contract whose value comes from the price or performance of something else, such as a stock, bond, commodity, or market index. For investors it acts like an insurance policy or a wager: it can be used to protect against losses, lock in prices, or amplify gains and losses, so it can change a portfolio’s risk and potential return without owning the underlying asset directly.
beneficially owned financial
"The total number of securities beneficially owned and as reported in Table I has been adjusted accordingly."
Beneficially owned describes securities or assets where a person has the economic rights and control—such as the right to receive dividends and to direct voting—even if legal title is held in another name. Think of it like having the keys and using a car that’s registered to someone else: you get the benefits and make decisions. Investors care because beneficial ownership reveals who truly controls value and voting power, affecting corporate decisions and takeover dynamics.
vest quarterly financial
"after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date."
AI-generated analysis. How Rhea-AI works. Not financial advice.
FAQ
What insider transactions did Trupanion (TRUP) CEO Margaret Tooth report?
Trupanion CEO Margaret Tooth reported a small open‑market sale and several equity award conversions. She sold 491 common shares and converted 19,042 restricted stock units into common stock, while additional shares were withheld by the issuer to satisfy tax obligations related to vesting.
Were any of the Trupanion (TRUP) CEO’s transactions tax withholdings rather than sales?
Yes. The filing states that 6,999 shares were withheld by Trupanion to cover income tax withholding and remittance obligations related to RSU vesting. It explicitly notes these tax‑withholding entries do not represent sales by CEO Margaret Tooth herself.
What equity awards are mentioned in the Trupanion (TRUP) CEO’s Form 4 footnotes?
Footnotes describe several RSU grants to the CEO, including awards of 5,000, 20,000, 48,679, 50,000, and 65,497 RSUs. Each grant vests over time, often with an initial vesting tranche followed by quarterly vesting, contingent on continued service through each vest date.
Did the Trupanion (TRUP) Form 4 include any corrections to prior ownership disclosures?
Yes. One footnote explains that an administrative error affected previously reported holdings. The total number of securities beneficially owned has been adjusted in this Form 4 so that the table now reflects the CEO’s current beneficial ownership as of the transaction dates.