Lemonade Inc SEC Filings

Adina Eckstein, Chief Operating Officer of Lemonade, Inc. (LMND), reported option exercise and a contemporaneous sale on 08/13/2025. She exercised 5,000 stock options at an exercise price of $24.47 and immediately sold 5,000 common shares at $58.00 per share pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024. The option exercised is fully vested. After these transactions, Ms. Eckstein beneficially owned 189,653 shares. The Form 4 was signed by an attorney-in-fact on her behalf on 08/15/2025.

The Form 144 filed for Lemonade, Inc. (LMND) reports a proposed sale of 5,000 common shares through Oppenheimer & Co. on the NYSE with an aggregate market value of $272,950. The shares were acquired on 06/07/2020 under an employee stock option plan and are to be paid in cash upon exercise on 08/13/2025. Outstanding shares are listed as 73,886,417, so the proposed sale equals roughly 0.0068% of outstanding stock. The filing also discloses three prior sales by the same person totaling 15,000 shares for $735,000 on 06/23/2025, 08/05/2025, and 08/11/2025. Signature and notice date fields are not shown in the provided content.

SoftBank Group Capital Ltd reports direct beneficial ownership of 5,958,698 shares of Lemonade, Inc. That holding represents 8.1% of Lemonade's common stock based on 73,266,170 shares outstanding as disclosed by the issuer. The Reporting Person states it has sole voting and sole dispositive power over these shares.

The filing also references the issuer's charter provision that any positive excess votes above 9.90% would be distributed pro rata to other stockholders; the disclosed position is below that threshold. The disclosure is a Schedule 13G amendment reporting ownership and voting/dispositive authority only.

Adina Eckstein, Chief Operating Officer of Lemonade, Inc. (LMND), reported transactions on Form 4 dated 08/11/2025. The filing discloses a sale of common stock executed pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024, with a reported sale price of $53. Following the reported transactions, Ms. Eckstein beneficially owns 189,653 shares of common stock.

The filing also reports a derivative entry for a stock option with an exercise/conversion price of $24.47 covering 5,000 underlying shares and shows 21,250 derivative securities beneficially owned following the transactions; the option is stated to be fully vested. The form was signed by an attorney-in-fact on 08/13/2025.

Lemonade, Inc. (LMND) filed a Form 144 disclosing a proposed sale of 38,155 shares of common stock through Fidelity Brokerage Services LLC (900 Salem Street, Smithfield, RI) on the NYSE with an aggregate market value of $2,289,300.00. The company shows 73,886,417 shares outstanding, so the proposed sale equals about 0.052% of outstanding shares.

The securities are reported as acquired under an option granted 02/06/2019, with the acquisition and planned sale dated 08/13/2025, and payment noted as cash. The filing also lists two prior sales by John Peters in the past three months: 1,494 shares on 06/03/2025 for $52,664.98 and 6,543 shares on 06/23/2025 for $294,435.00. Other filer and notice administrative fields are not populated in the provided content.

Lemonade insider Adina Eckstein filed a Form 144 notifying a proposed sale of 5,000 common shares to be executed through Oppenheimer & Co. on 08/11/2025 with an aggregate market value of $244,900. The shares were acquired on 06/07/2020 under an employee stock option plan and will be paid in cash upon exercise. The filing lists 73,886,417 shares outstanding, making the proposed block about 0.0068% of outstanding stock. The filer disclosed two recent sales in the past three months totaling 10,000 shares for $470,000 in gross proceeds. The notice includes the standard representation that the filer is not aware of any undisclosed material adverse information.

Form 144 filed for Lemonade, Inc. (LMND) notifying a proposed sale of common stock and disclosure of recent related transactions.

• Proposed sale: 5,000 common shares via Oppenheimer & Co.; aggregate market value $239,650; approximate sale date 08/05/2025; exchange: NYSE.
• Outstanding shares: 73,886,417.
• Acquisition details: 1,250 shares acquired 12/24/2019 (Employee Stock Option Plan); 3,750 shares acquired 06/07/2020 (Employee Stock Option Plan).
• Recent sale (past 3 months): Adina Eckstein sold 5,000 shares on 06/23/2025 for gross proceeds $225,000.

The filer represents no undisclosed material adverse information and includes standard signature/attestation language required by Form 144.

Lemonade (LMND) delivered Q2-25 top-line growth but remains unprofitable. Total revenue rose 34% YoY to $164.1 million, driven by a 26% increase in net earned premium (to $112.5 million) and higher ceding-commission income. Loss and LAE grew more slowly, improving the loss ratio to ~69% (vs. ~79% a year ago). Sales & marketing spend jumped 62% to $59.6 million as the company pursues expansion. Net loss narrowed to $43.9 million (-$0.60 per share) from $57.2 million (-$0.81), while weighted shares rose 3.8% to 73.4 million.

Operating cash outflow was $41.7 million for H1-25, in line with H1-24, and cash/​equivalents held steady at $386 million. Borrowings under the General Catalyst marketing-finance facility increased to $123.5 million (from $83.4 million), boosting leverage but providing growth capital. Stock-based compensation fell to $25.7 million (H1-24: $30.3 million). Book value declined to $527.1 million as the accumulated deficit widened to $1.41 billion.

The reinsurance program was renewed on 1 Jul 25 with a sharply lower cession rate (~20% vs. ~55%), increasing Lemonade’s retained risk from Q3 onward. Q2 results include $16.9 million of California wildfire losses and a $6.9 million FAIR Plan assessment, partially offset by an $11.7 million Employee Retention Credit refund. Termination of the Chewy warrant agreement removed 3.17 million potential shares and reversed $5.2 million of previously accrued expense.