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.
The Vanguard Group filed an amendment reporting 0 shares (0%) of Lemonade Inc. common stock as beneficially owned. The filing explains Vanguard completed an internal realignment on January 12, 2026, and certain subsidiaries will report ownership separately going forward.
The filing is signed on March 27, 2026 by Ashley Grim, Head of Global Fund Administration, and states no single outside person holds more than 5% of the class in the accounts reported.
Wininger Shai reported acquisition or exercise transactions in this Form 4 filing.
Lemonade, Inc. president and director Shai Wininger reported two stock awards of common shares as compensation. He received an award of 820,000 restricted stock units, granted at a price of $0.0000 per share, increasing his direct holdings to 4,238,749 shares after that award and 4,418,749 shares after a second award.
The 820,000 restricted stock units vest quarterly over 8 years beginning on June 1, 2026, with 5% vesting during the first year, then 10%, 15%, 20%, 20%, 15%, 10% and 5% in subsequent years, subject to continued employment. He also received 180,000 performance restricted stock units that vest only if the company’s stock sustains a $110 closing price for at least 30 consecutive trading days within 24 months of the grant date. Each unit represents a contingent right to one share of common stock.
Schreiber Daniel A. reported acquisition or exercise transactions in this Form 4 filing.
Lemonade, Inc. reported that Chief Executive Officer Daniel Schreiber received two equity awards of common stock on March 18, 2026. He was granted 820,000 restricted stock units that vest quarterly over eight years, beginning June 1, 2026, with vesting percentages increasing in later years.
He was also granted 180,000 performance restricted stock units that vest only if the company’s stock sustains a closing price of $110 for at least 30 consecutive trading days within 24 months of the grant date. Following these awards, he holds over one million shares directly and additional shares indirectly through Dan and Dan Ltd., where he has voting and dispositive control.
Angelidis-Smith Maria reported acquisition or exercise transactions in this Form 4 filing.
Lemonade, Inc. director Maria Angelidis-Smith reported stock awards rather than market purchases. On March 10, 2026, she received 3,350 shares of common stock directly at $55.30 per share, bringing her direct holdings to 14,896 shares. On the same date, 5,390 shares at $55.70 per share were awarded to the Smith Family Trust, where she is co-trustee with voting and dispositive control, increasing those indirect holdings to 38,944 shares.
Lemonade, Inc. Chief Operating Officer Adina Eckstein received two equity awards. She was granted 145,112 shares of common stock as restricted stock units and 54,417 stock options with an exercise price of $55.13 per share. After the grant, she directly holds 333,503 common shares. Both the RSUs and options vest quarterly over eight years, beginning in June 2026, with smaller portions vesting in early years and larger portions in years three to five. These awards are compensation grants rather than open-market purchases or sales.
Prosor Maya reported acquisition or exercise transactions in this Form 4 filing.
Lemonade, Inc. Chief Business Officer Maya Prosor received a grant of 181,389 restricted stock units, each representing one share of common stock. The RSUs begin vesting quarterly on June 1, 2026, over eight years, with small portions vesting each year, subject to her continued employment. Following this award, she holds 188,793 shares directly and 29,286 shares indirectly through Cohen Holdings, LLC, over which she has voting and dispositive control. This is a compensation-related equity grant, not an open-market stock purchase.
Timothy E. Bixby, Chief Financial Officer of Lemonade, Inc. completed an open-market sale of 2,135 shares of common stock on March 3, 2026 at $50.12 per share. The sale was not discretionary and was made to cover tax withholding from vesting Restricted Stock Units. Following this transaction, he directly holds 249,490 shares.
Lemonade, Inc. Chief Insurance Officer John Sheldon Peters reported selling a total of 5,344 shares of common stock in open‑market transactions. He sold 1,773 shares on March 3, 2026 at $50.12 per share and 3,571 shares on March 4, 2026 at $52.50 per share.
After these transactions, he directly owned 80,300 shares following the March 3 sale and 76,729 shares following the March 4 sale. A footnote explains that part of the reported selling was not discretionary and represented shares sold to cover tax withholding obligations tied to vesting and settlement of restricted stock units, and another footnote states that a sale was made under a Rule 10b5‑1 trading plan.
Lemonade, Inc.'s Chief Business Officer, Maya Prosor, reported a non‑discretionary sale of 223 shares of common stock on March 3, 2026, at $50.12 per share. The shares were sold to cover tax withholding obligations tied to vesting and settlement of restricted stock units.
After this transaction, Prosor directly holds 7,404 common shares and indirectly holds 29,286 common shares through Cohen Holdings, LLC, over which she has voting and dispositive control.
John S. Peters reported sales of Common Stock in Form 144. The filing lists four reported dispositions: 12/10/2025 3,554 shares for $287,874; 01/06/2026 10,000 shares for $800,000; 01/22/2026 9,000 shares for $810,000; and 03/03/2026 1,773 shares for $88,867.02.
The filing also shows 3,571 restricted shares listed as vesting on 03/01/2026 under compensation. The transactions were reported through Fidelity Brokerage Services LLC.