Welcome to our dedicated page for Lemonade SEC filings (Ticker: LMND), a comprehensive resource for investors and traders seeking official regulatory documents including 10-K annual reports, 10-Q quarterly earnings, 8-K material events, and insider trading forms.
Lemonade, Inc. filings document operating results, governance, and capital-structure matters for its digital insurance business. Form 8-K reports furnish shareholder letters covering insurance operating metrics, financial condition, underwriting performance, profitability measures, and cash-flow disclosures.
The company's proxy materials address board and executive compensation matters, including equity-award and pay-versus-performance disclosures. Its SEC record also includes capital-structure and security-status filings related to warrants to purchase common stock, including exchange suspension, expiration, and Form 25 removal from listing and registration on NYSE American.
Lemonade Chief Operating Officer Adina Eckstein executed a significant insider transaction on June 23, 2025, involving both the exercise of stock options and subsequent sale of shares:
- Exercised 5,000 stock options at $23.69 per share
- Immediately sold 5,000 shares at $45.00 per share
- The sale was conducted under a pre-established Rule 10b5-1 trading plan from December 5, 2024
- After the transactions, Eckstein holds 189,653 shares directly and 1,250 stock options
The transaction resulted in a gross profit of approximately $106,550 (($45.00 - $23.69) × 5,000 shares). The options were fully vested at the time of exercise, with an original expiration date of September 25, 2029.
Lemonade CFO Timothy E. Bixby reported significant insider trading activity on June 23, 2025. The transaction involved two key parts:
- Exercised 11,000 stock options at $23.69 per share through conversion (Transaction Code: M)
- Subsequently sold 11,000 shares at $43.36 per share under a pre-established Rule 10b5-1 trading plan from December 2024
Following these transactions, Bixby's holdings include:
- Direct ownership: 263,393 common shares and 311,300 stock options
- Indirect ownership: 30,000 shares held in the Timothy E. Bixby Family Trust
The exercised options were fully vested with an expiration date of September 25, 2029. This transaction resulted in a gross profit of approximately $216,370 (difference between sale price and option exercise price).
Lemonade Chief Insurance Officer John Peters executed significant stock transactions on June 23, 2025, as reported in this Form 4 filing. The transactions involved:
- Exercise of stock options for 6,543 shares at $5.26 per share
- Immediate sale of all 6,543 shares at $45.00 per share under a pre-established Rule 10b5-1 trading plan from August 30, 2024
Following these transactions, Peters retains 106,115 shares of common stock held directly, plus 28,457 vested stock options. The options have an exercise price of $5.26 and expire on March 27, 2028. This transaction pattern of exercising options and selling shares was executed according to a predetermined trading plan, suggesting planned portfolio management rather than a reactive market decision.
A Form 144 has been filed for Lemonade indicating a proposed sale of 5,000 shares of common stock with an aggregate market value of $221,550. The securities are to be sold through Oppenheimer & Co. Inc. on the NYSE, with an approximate sale date of June 23, 2025.
The shares were originally acquired through an Employee Stock Option Plan on December 24, 2019, with the filer receiving 20,000 shares from the issuer. Payment is to be made in cash upon execution of the sale.
Key details:
- Current shares outstanding: 73,266,170
- Sale price per share: approximately $44.31
- No other securities were sold by the filer during the past 3 months
- Transaction to be executed on the NYSE
Form 4 Snapshot: On 06/16/2025 Lemonade, Inc. (LMND) Chief Financial Officer Timothy E. Bixby exercised 11,000 fully-vested stock options at an exercise price of $23.69. Immediately thereafter, he sold the same 11,000 common shares in two open-market trades executed under a Rule 10b5-1 plan adopted 12/12/2024.
Transaction detail
- 5,000 shares sold at $41.06
- 6,000 shares sold at $42.50
- Gross sale proceeds ≈ $711,000
- Option exercise cost ≈ $260,590
Because the amount sold matched the option shares acquired, Bixby’s direct share count returned to its pre-transaction level of 263,393. He also retains 30,000 shares held indirectly through the Timothy E. Bixby Family Trust and continues to hold 322,300 outstanding stock options that expire 09/25/2029.
Investor considerations
- The sale was pre-scheduled, limiting negative signalling risk.
- No net change in direct share ownership preserves management-shareholder alignment.
- CFO still controls roughly 293k total shares (direct + trust), indicating a substantial ongoing stake.