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.
Form 144 notice for Lemonade, Inc. (LMND): The filer reports a proposed sale of 282 common shares through Fidelity Brokerage Services with an aggregate market value of $14,196.53. The shares were acquired via restricted stock vesting on 08/29/2025 and payment was recorded as compensation on the same date. The approximate sale date is listed as 09/03/2025 and the securities trade on the NYSE. The filing shows 73,886,417 shares outstanding. The filer also disclosed a prior sale on 06/03/2025 of 252 shares for $8,883.25. The notice includes the required representation that the seller is not aware of undisclosed material adverse information.
Lemonade, Inc. (LMND) filing a Form 144 reports proposed sale of restricted common stock by an insider. The notice states 2,718 shares held at Fidelity Brokerage will be offered with an aggregate market value of $136,830.37, and an approximate sale date of 09/03/2025 on the NYSE. The shares were acquired by restricted stock vesting on 08/29/2025 and received as compensation. The filing lists prior sales by the same person within three months: 1,494 shares (06/03/2025), 6,543 shares (06/23/2025), and 38,155 shares (08/13/2025) with gross proceeds shown.
Shai Wininger, President and Director of Lemonade, Inc. (LMND), received a grant of stock options covering 127,780 shares with an exercise price of $59.74. The option award was reported as a transaction dated 08/21/2025 and the form was signed on 08/25/2025 by an attorney-in-fact. The filing states the option will vest in 12 equal quarterly installments beginning on 08/18/2025, subject to continued employment, and the option expires on 08/18/2035. After the reported grant, the reporting person beneficially owns 127,780 shares directly attributable to this option position.
Adina Eckstein, Chief Operating Officer of Lemonade, Inc. (LMND), was granted 38,334 restricted stock units on 08/21/2025. Each restricted stock unit represents a contingent right to receive one share of Lemonade common stock and will vest in 12 equal quarterly installments beginning August 1, 2025, subject to the reporting person's continued employment through each vesting date. After the reported grant, the filing shows the reporting person beneficially owns 227,987 shares of common stock. The Form 4 was signed by Timothy Bixby as attorney-in-fact on 08/25/2025.
Daniel A. Schreiber, Chief Executive Officer and Director of Lemonade, Inc. (LMND), was granted a stock option on 08/21/2025 covering 127,780 underlying shares with an exercise price of $59.74. The option is exercisable in 12 equal quarterly installments beginning 08/18/2025 and expires 08/18/2035, and the shares are reported as directly owned. Following the reported grant, the filing shows 127,780 common shares underlying the option beneficially owned by the reporting person. The grant is subject to continued employment through each vesting date.
John Sheldon Peters, Chief Insurance Officer of Lemonade, Inc. (LMND), was granted a stock option covering 25,556 shares with an exercise price of $59.74. The reported transaction date is 08/21/2025 and the Form 4 was filed on 08/25/2025. The option vests in 12 equal quarterly installments beginning 08/18/2025 and becomes exercisable according to that schedule, with an expiration date of 08/18/2035. After this grant, the reporting person directly beneficially owns 25,556 common shares (from this option) at a stated price of $0 for the reported beneficial ownership figure. The form was signed by an attorney-in-fact on behalf of the reporting person.
Maya Prosor, Chief Business Officer of Lemonade, Inc. (LMND), was granted stock options totaling 76,668 shares on 08/21/2025. The options have an exercise price of $59.74 and expire on 08/18/2035. The filing reports that the option will vest in 12 equal quarterly installments beginning on 08/18/2025, subject to the reporting person remaining employed through each vesting date.
The Form 4 shows the reporting person directly beneficially owns 76,668 shares following the transaction. The document is signed by Timothy Bixby as attorney-in-fact for Maya Prosor and dated 08/25/2025.
Timothy E. Bixby, Chief Financial Officer of Lemonade, Inc. (LMND), was granted a stock option on 08/21/2025 for 127,780 shares with an exercise price of $59.74 per share. The option vests in 12 equal quarterly installments beginning on 08/18/2025 and expires on 08/18/2035. The report indicates the shares underlying the option total 127,780 common shares and are listed as directly beneficially owned following the transaction. Vesting is conditioned on the reporting person’s continued employment through each vesting date. The Form 4 is signed by Mr. Bixby on 08/25/2025.
John Peters, Chief Insurance Officer at Lemonade, Inc. (LMND), reported multiple transactions affecting his beneficial ownership. The filing shows a charitable donation of 1,000 common shares on 08/12/2025 with no value received. On 08/13/2025 he acquired 38,155 common shares by exercising a fully vested stock option at an exercise price of $11.61 per share. The same day he sold 38,155 common shares pursuant to a Rule 10b5-1 trading plan at a sale price of $60.00 per share. Following these transactions his reported beneficial ownership is 105,115 shares.
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.