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, Inc. reported an insider stock sale by its Chief Insurance Officer, John Peters. On 12/10/2025, he sold 3,554 shares of common stock at a price of $81 per share, in a transaction coded "S" for sale.
After this transaction, Peters beneficially owns 70,771 shares of Lemonade common stock, held directly. The filing is a routine Form 4 report of insider trading activity and does not describe any derivative securities transactions.
Lemonade, Inc. insider plans to sell a small block of shares under Rule 144. The notice covers the proposed sale of 4,200 shares of common stock through Fidelity Brokerage Services LLC on or about 12/11/2025, to be sold on the NYSE. The aggregate market value of the shares listed is $351,081.78, compared with 74,731,027 common shares shown as outstanding. The securities to be sold stem from restricted stock vesting awards from the issuer, including 3,641 shares acquired on 11/21/2024 and 559 shares acquired on 11/21/2025, both recorded as compensation rather than cash purchases. The signer represents that they are not aware of undisclosed material adverse information about Lemonade’s operations.
Lemonade, Inc.’s Chief Operating Officer, Adina Eckstein, reported multiple stock transactions in early December 2025. On December 8 and 9, 2025, she exercised employee stock options with exercise prices of $24.47 and $44.57 per share, converting them into Lemonade common stock. She also reported several open-market sales of common shares on those dates at prices ranging from about $77.17 to $78.97 per share.
After the reported transactions, Eckstein directly beneficially owned 204,229 shares of Lemonade common stock. The filing notes that the reported sales were made pursuant to a pre-arranged Rule 10b5-1 trading plan adopted on September 8, 2025. The derivative securities table shows the corresponding option exercises and the remaining stock options held following these transactions.
Lemonade insider plans additional stock sale under Rule 144. A holder of Lemonade common stock filed a notice to sell 3,554 shares through Fidelity Brokerage Services on the NYSE, with an aggregate market value of $287,874 and 74,731,027 common shares outstanding. The shares to be sold were acquired on 12/01/2024 via restricted stock vesting as compensation from the issuer. The same seller has already completed multiple common stock sales over the prior three months, including 18,930 shares on 11/20/2025 for gross proceeds of $1,377,536.10.
LMND shareholder Adina Eckstein filed a notice to sell 7,919 shares of common stock through broker Oppenheimer & Co. Inc. on the NYSE, with an aggregate market value of 626,947.00. The filing reports that 74,731,027 shares of this class were outstanding. The shares to be sold relate to common stock, and the form confirms the filer’s representation that they are unaware of any undisclosed material adverse information about the issuer.
The notice also details that Eckstein previously acquired 56,252 common shares on 02/07/2023 via an RSU transaction with the issuer. Over the past three months, she sold multiple blocks of common shares, including 40,000 shares on 11/07/2025 and 41,557 shares on 12/08/2025, generating significant gross proceeds. This document outlines planned and recent sales rather than changes to the issuer’s operations.
LMND filed a Form 144 notice for a planned sale of common stock under Rule 144. The notice covers 70,794 shares of common stock to be sold through broker Oppenheimer & Co. Inc. on the NYSE, with an aggregate market value of $5,590,602.18. The filing states that 74,731,027 shares of the issuer’s common stock are outstanding. The securities relate to stock acquired through an employee stock option plan and restricted stock units over several years.
The notice also discloses that Adina Eckstein has sold common shares of the issuer during the prior three months, including 40,000 shares on 11/07/2025 for gross proceeds of $2,920,868.00 and 5,988 shares on 11/17/2025 for gross proceeds of $467,064.00. By signing the notice, the seller represents that they are not aware of any material adverse, nonpublic information about the issuer’s current or prospective operations.
Lemonade, Inc. reported that its Chief Financial Officer, Timothy Bixby, sold 2,862 shares of common stock on 12/02/2025 at a price of $72.74 per share. According to the filing, the sale was not a discretionary trade, but shares sold to cover tax withholding obligations tied to the vesting and settlement of Restricted Stock Units. After this transaction, Bixby beneficially owned 251,625 Lemonade common shares directly.
Lemonade, Inc. insider activity: Chief Business Officer Maya Prosor reported a small sale of Lemonade common stock. On 12/02/2025, 198 shares of common stock were sold at a price of $72.74 per share. The filing explains that this sale was not a discretionary trade, but shares sold to cover tax withholding obligations tied to the vesting and settlement of Restricted Stock Units.
After this transaction, Prosor beneficially owns 7,627 shares directly and 29,286 shares indirectly through Cohen Holdings, LLC, over which she has voting and dispositive control. The form is filed as an individual Form 4 for one reporting person.
Lemonade, Inc. reported insider share sales by its Chief Insurance Officer, John Peters. On 12/02/2025, Peters sold 2,677 shares of common stock at $72.74 per share to cover tax withholding obligations tied to the vesting and settlement of Restricted Stock Units. On 12/03/2025, he sold an additional 2,667 shares at $72.37 per share under a Rule 10b5-1 trading plan, which is a pre-arranged program for trading company stock. After these transactions, Peters beneficially owned 74,325 shares of Lemonade common stock, held directly.
A shareholder of LMND has filed a Rule 144 notice to sell common stock through Fidelity Brokerage Services on the NYSE. The filing covers a proposed sale of 2,667 common shares with an aggregate market value of $193,010.79, against 74,731,027 common shares outstanding. These shares were acquired on 12/01/2025 through restricted stock vesting from the issuer as compensation, with payment also dated 12/01/2025.
The same shareholder, identified as John S. Peters, reports prior sales of common stock over the last three months, including 2,718 shares on 09/03/2025 for $136,830.37 and 18,930 shares on 11/20/2025 for $1,377,536.10, among other transactions. By signing the notice, the seller represents that they do not know of any undisclosed material adverse information about the issuer’s operations.