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.
John S. Peters reported proposed sales of Common shares under Rule 144, including a planned disposition of 1,773 shares tied to restricted stock vesting on 02/27/2026. The filing also lists four transactions during the past three months: 2,667 shares on 12/03/2025 ($193,010.79), 3,554 shares on 12/10/2025 ($287,874.00), 10,000 shares on 01/06/2026 ($800,000.00), and 9,000 shares on 01/22/2026 ($810,000.00).
Lemonade, Inc. is a digital-first insurer using artificial intelligence, data and a vertically integrated platform to sell renters, homeowners, pet, car and life insurance in the U.S., Europe and the UK. Customers buy and manage policies through chatbots like AI Maya, while AI Jim automates about 55% of claims, with 96% of first notices of loss taken without human intervention as of December 31, 2025.
The company remains unprofitable, posting a net loss of $165.5 million in 2025 versus $202.2 million in 2024, and an accumulated deficit of $1,464.3 million. As of February 24, 2026, it had 76,383,438 common shares outstanding and about 3 million customers, with roughly 2,300 customers per employee.
Lemonade relies heavily on reinsurance, ceding around 55% of its book through June 30, 2025 and about 20% through June 30, 2026, to reduce capital needs and earnings volatility. In 2025 it absorbed net losses of about $19.6 million from the January California wildfires and a $6.9 million FAIR Plan assessment. Key risks include persistent losses, competitive pressure from large incumbents and insurtechs, regulatory and data-privacy burdens, catastrophe exposure, and the performance of its proprietary AI-driven underwriting and claims systems.
Lemonade, Inc. reported its strongest quarter to date in Q4 2025, combining rapid growth with sharply improved profitability metrics. In force premium reached $1.24 billion, up 31% year over year, while revenue rose 53% to $228.1 million as the customer base grew 23% to about 3.0 million.
Gross profit increased 73% to $110.6 million, lifting gross profit margin to 48%, helped by an improved gross loss ratio of 52% versus 63% a year earlier. Net loss narrowed to ($21.7) million from ($30.0) million, and Adjusted EBITDA loss improved to ($4.6) million from ($23.8) million. Adjusted free cash flow was $36.7 million, up from $26.5 million, and cash, cash equivalents and investments totaled about $1.12 billion at year-end, with roughly $250 million required as regulatory surplus.
The company highlighted strong growth and underwriting trends in Pet, Car, and Europe, and set 2026 guidance for in force premium of $1.63 billion at the high end, revenue of up to $1.192 billion, and full-year Adjusted EBITDA loss between ($52) and ($48) million. Management reiterated expectations for positive Adjusted EBITDA in Q4 2026 and for 2027 to be its first full year of Adjusted EBITDA profitability.
Lemonade, Inc. Chief Insurance Officer John Sheldon Peters exercised stock options to acquire 11,845 shares of common stock at $11.61 per share on 02/12/2026. This derivative conversion increased his directly held common stock to 82,073 shares, while the exercised stock option position was reduced to zero.
Lemonade, Inc. is having its warrants to purchase common stock removed from listing and registration on the NYSE American. The exchange states it has followed its rules to strike this class of securities, and the company has complied with the exchange’s requirements for voluntary withdrawal.
Lemonade, Inc. insider transaction: An entity associated with Chief Executive Officer Daniel Schreiber, Dan and Dan Ltd., sold 9,108 shares of Lemonade common stock on January 23, 2026 at a weighted average price of $99.04 per share. The sale was made under a pre-arranged Rule 10b5-1 trading plan adopted on December 11, 2024. After this transaction, 1,514,426 shares of Lemonade common stock were beneficially owned indirectly through Dan and Dan Ltd., over which Schreiber has voting and dispositive control.
Lemonade, Inc. filed an update on its publicly traded warrants that were originally issued in connection with its November 8, 2021 merger with Metromile, Inc. The company has 7,846,646 warrants outstanding, each with an exercise price of $218.51 and listed on the New York Stock Exchange under the symbol LMND-WS.
These warrants are scheduled to expire on Monday, February 9, 2026 at 5:00 p.m. Eastern Time. To allow for timely settlement of any final trades, the New York Stock Exchange has notified Lemonade that it will suspend trading of the warrants after the close of market on Thursday, February 5, 2026.
Lemonade, Inc. insider reporting shows that Dan and Dan Ltd., an entity controlled by Chief Executive Officer and director Daniel A. Schreiber, sold 126,625 shares of common stock on January 22, 2026. The sale was made under a Rule 10b5-1 trading plan that was adopted on December 11, 2024, meaning the trades were pre-arranged according to preset instructions.
The filing reports a weighted average sale price of $94.74 per share, with the shares sold in multiple transactions. After this transaction, 1,523,534 shares of Lemonade common stock are reported as beneficially owned indirectly, held by Dan and Dan Ltd., over which Schreiber has voting and dispositive control.