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 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.
Lemonade, Inc. (LMND) insider plans additional share sale under Rule 144. A holder has filed to sell 2,677 shares of Lemonade common stock through Fidelity Brokerage Services on the NYSE, with an aggregate market value of $194,711.06 and an approximate sale date of 12/02/2025. The filing notes that 74,731,027 shares of Lemonade common stock are outstanding.
The 2,677 shares to be sold were acquired on 12/01/2025 via restricted stock vesting from the issuer as compensation. Over the past three months, the same seller reported additional sales of Lemonade common stock, including 2,718 shares on 09/03/2025 for gross proceeds of $136,830.37, 18,930 shares on 11/20/2025 for $1,377,536.10, and 3,789 shares on 11/24/2025 for $278,205.02. The signer represents that they are not aware of undisclosed material adverse information about Lemonade.
Lemonade, Inc. insider plans small Rule 144 stock sale. A holder intends to sell 198 shares of Lemonade common stock through Fidelity Brokerage Services on 12/02/2025 on the NYSE, with an indicated aggregate market value of $14,401.49. These shares were acquired on 12/01/2025 through restricted stock vesting from the issuer as compensation.
The notice also reports that the same seller, Maya Prosor, sold 282 shares of Lemonade common stock on 09/03/2025 for gross proceeds of $14,196.53. The filer represents that they are not aware of any material adverse, nonpublic information about Lemonade’s current or prospective operations.
Lemonade, Inc. (LMND) reported an insider stock sale by its Chief Insurance Officer, John Peters. On 11/20/2025 he sold 18,930 shares of common stock at $72.77 per share, and on 11/24/2025 he sold an additional 3,798 shares at $73.25 per share, all coded as sales. After these transactions, he beneficially owned 79,669 shares of Lemonade common stock in direct ownership. The filing states that the 11/20/2025 sale was made pursuant to a Rule 10b5-1 trading plan adopted on August 22, 2025.
Shareholder John S. Peters filed a Form 144 for issuer LMND to sell 3,798 shares of common stock through Fidelity Brokerage Services LLC. The filing lists an aggregate market value of $278,205.02 for this planned sale, with 74,731,027 shares of the issuer’s common stock outstanding. The shares to be sold were acquired on 09/01/2024 via restricted stock vesting from the issuer as compensation.
The notice also reports prior sales by Peters over the past three months, including 18,930 shares of common stock sold on 11/20/2025 for gross proceeds of $1,377,536.10 and 2,718 shares sold on 09/03/2025 for $136,830.37. The planned sale is expected around 11/24/2025 on the NYSE.
A shareholder of Lemonade, Inc. (LMND) has filed a Form 144 notice to potentially sell 18,930 shares of common stock through Fidelity Brokerage Services LLC on the NYSE. The filing lists an aggregate market value of about $1,377,536.10 for these shares, with 74,731,027 shares of common stock shown as outstanding and an approximate sale date of 11/20/2025. The shares to be sold were acquired mainly through restricted stock vesting and a stock option exercise between 2023 and 2024. Over the past three months, the same seller, John S. Peters, previously sold 2,718 shares of common stock for gross proceeds of $136,830.37, according to this notice.
Lemonade, Inc. (LMND): SoftBank Group Capital Ltd filed an amended Schedule 13G reporting beneficial ownership of 3,563,924 shares of common stock, representing 4.8% of the class as of September 30, 2025, based on 74,731,027 shares outstanding as of November 4, 2025.
SoftBank reports sole voting power over 3,563,924 shares and sole dispositive power over 3,563,924 shares, with no shared power. The filing notes the joint investment committee to which SoftBank had delegated voting and dispositive power was dissolved on March 31, 2023.