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. (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.
Lemonade, Inc. (LMND) disclosed insider activity by its Chief Financial Officer, Timothy E. Bixby. On 11/07/2025, he made a charitable gift of 6,000 shares of common stock at $0. On 11/11/2025, he sold 30,000 shares indirectly held by the Timothy E. Bixby Family Trust at a price of $75.51 per share.
Following these transactions, Bixby beneficially owned 254,487 shares directly. Indirect holdings held by the Trust were 0 shares after the sale.
Lemonade, Inc. (LMND) reported insider activity by COO Adina Eckstein on Form 4. She exercised stock options at $27.35 and sold the resulting shares in open‑market transactions.
On Nov 7, 2025, she exercised 20,000 options and sold 20,000 shares at $72.04, then exercised another 20,000 and sold 20,000 at $74.00. On Nov 10, 2025, she exercised 5,988 options and sold 5,988 shares at $78.00. Following these transactions, she held 227,987 shares directly.
The exercised options carried a $27.35 exercise price, are noted as fully vested, and are listed with an expiration of Apr 5, 2032.
Lemonade, Inc. (LMND) disclosed an insider transaction by CEO and Director Daniel Schreiber. On 11/11/2025, he reported a gift (Code G) of 35,000 shares of common stock at a reported price of $0, described as a transfer to a third party with no value received. Following the gift, Schreiber’s beneficial ownership stands at 24,327 shares, held directly.
Lemonade, Inc. (LMND) — Form 144 notice of proposed sale: A holder filed to sell 30,000 shares of Common Stock through Charles Schwab Corporation, with an aggregate market value of $2,265,144.00. The filing lists an approximate sale date of 11/11/2025 on the NYSE.
The filing shows 74,731,027 shares outstanding. It also discloses a prior sale in the past three months: 2,906 shares sold on 09/03/2025 by Timothy Bixby for $146,294.73.