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 that Chief Insurance Officer John Sheldon Peters sold common stock in a planned transaction. On January 22, 2026, he sold 9,000 shares of common stock at $90 per share in an open market sale coded as a disposition. The transaction was executed under a Rule 10b5-1 trading plan adopted on August 22, 2025, indicating it was pre-arranged rather than opportunistic.
Following this sale, Peters beneficially owns 70,228 shares of Lemonade common stock, held directly. The filing shows no derivative securities activity in this period.
A shareholder of the issuer for LMND has filed a notice of proposed sale under Rule 144 covering 144,000 shares of common stock to be sold through Goldman Sachs & Co. LLC. The filing lists an aggregate market value of $13,906,080 for these shares and notes that 74,731,027 shares of the class were outstanding, with an approximate sale date of January 22, 2026 on the NYSE. The notice also reports that 35,000 common shares were sold during the prior three months by Daniel Schreiber for $2,769,900 in gross proceeds.
A shareholder of LMND has filed a Rule 144 notice to sell 9,000 shares of common stock through Fidelity Brokerage Services LLC on the NYSE, with an approximate sale date of 01/22/2026. The shares to be sold have an indicated aggregate market value of 810000.00, and the filing reports that 74,731,027 shares of the same class are outstanding.
The 9,000 shares were acquired on 01/02/2025 via a stock option exercise from the issuer, paid in cash. The filing also lists prior sales over the past three months by John S. Peters, including a sale of 10,000 shares on 01/06/2026 for 800000.00.
JPMorgan Chase & Co. reported a passive ownership stake in Lemonade, Inc. common stock as of 12/31/2025. The firm disclosed beneficial ownership of 4,482,950 shares, representing 5.9% of the class. JPMorgan has sole voting power over 2,306,747 shares and shared voting power over 43 shares, with sole dispositive power over 4,477,816 shares and shared dispositive power over 4,464 shares.
The filing is made on a Schedule 13G basis, meaning JPMorgan certifies the shares were acquired and are held in the ordinary course of business and not for the purpose of changing or influencing control of Lemonade.
Lemonade, Inc. reported an insider equity transaction by Chief Insurance Officer John Sheldon Peters. On January 8, 2026, Peters exercised a stock option to acquire 18,457 shares of Lemonade common stock at an exercise price of $5.26 per share, reflected as a code "M" transaction. This exercise converted derivative securities (options) into common stock rather than representing an open-market purchase or sale.
After the transaction, Peters beneficially owned 79,228 shares of Lemonade common stock in direct form and held 10,000 stock options directly. The filing notes that the option involved in the transaction was fully vested and exercisable.
Lemonade, Inc. disclosed that Chief Insurance Officer John Peters sold shares of company stock. On January 6, 2026, he sold 10,000 shares of common stock at $80 per share in a planned transaction under a Rule 10b5-1 trading plan adopted on August 22, 2025. After this sale, he directly owned 60,771 shares of Lemonade common stock.
LMND – Planned insider sale under Rule 144
An affiliate of the issuer has filed a notice to sell 10,000 shares of common stock through Fidelity Brokerage Services on the NYSE, with an approximate sale date of 01/06/2026. The filing shows 74,731,027 common shares outstanding for the issuer.
The 10,000 shares to be sold were acquired on 12/31/2024 via a stock option exercise from the issuer, paid in cash. Over the past three months, the filer, identified as John S. Peters of New York, has already sold several blocks of common shares, including 18,930 shares for gross proceeds of $1,377,536.10 on 11/20/2025, along with multiple smaller trades in late November and December 2025.
Lemonade, Inc. reported an insider stock sale by Chief Operating Officer Adina Eckstein. On December 11, 2025, Eckstein sold 7,919 shares of Lemonade common stock in an open market transaction coded as a sale. The shares were sold at a weighted average price of $84.15 per share, with the trade executed in multiple transactions at different prices.
The filing states that the sale was made pursuant to a Rule 10b5-1 trading plan adopted on September 8, 2025. After this transaction, Eckstein beneficially owned 188,391 shares of Lemonade common stock, held directly.
Lemonade, Inc. director Debra Schwartz reported selling 4,200 shares of common stock on 12/11/2025 at a weighted average price of $83.59 per share.
After this transaction, she beneficially owns 21,567 shares directly. The sale was executed through multiple trades, with individual prices ranging from $83.56 to $83.76.
Lemonade, Inc.’s Chief Operating Officer Adina Eckstein reported a sale of 7,919 shares of common stock on December 10, 2025. The transaction, coded as a sale, was carried out under a pre-arranged Rule 10b5-1 trading plan adopted on September 8, 2025, which is designed to allow insiders to trade according to a preset schedule. The weighted average price for the shares was $81.15 per share.
Following this transaction, Eckstein beneficially owns 196,310 shares of Lemonade common stock in direct ownership. The filing notes that the reported price reflects multiple trades and that full trade-by-trade pricing details are available on request.