Every Form 4 that Lemonade, Inc. (LMND) has filed with the SEC in the last 12 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.
A Form 4 covers the transactions officers, directors and large holders report, so if you follow LMND and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full LMND filings page.
Lemonade, Inc. (LMND) reported that Chief Business Officer Maya Prosor had 1,040 shares of common stock sold on September 3, 2026 at $54.63 per share. A footnote states these shares were sold to cover tax withholding obligations from the vesting of Restricted Stock Units and were not a discretionary trade. After this transaction, she held 186,533 shares directly and 29,286 shares indirectly through Cohen Holdings, LLC, over which she has voting and dispositive control. No Rule 10b5-1 trading plan is reported.
Lemonade, Inc. (LMND) reported that its Chief Financial Officer, Timothy E. Bixby, had 1,893 shares of common stock sold on September 3, 2026 at $54.63 per share. According to the company’s disclosure, this sale was not a discretionary trade but shares withheld and sold to cover tax obligations arising from the vesting and settlement of restricted stock units. After this transaction, Bixby’s direct holdings were 172,370 shares of Lemonade common stock.
Lemonade, Inc. (LMND) reported that Chief Insurance Officer John Sheldon Peters disposed of common stock in two transactions. On September 3, 2026, 859 shares were sold at $54.63 per share in a non-discretionary transaction to cover tax withholding obligations related to vesting and settlement of Restricted Stock Units. On September 4, 2026, 2,249 shares were sold at $54.45 per share pursuant to a Rule 10b5-1 trading plan, with no post-transaction holdings reported in this filing.
Lemonade, Inc. (LMND) reported that President and director Shai Wininger made a bona fide gift of 1,876 shares of common stock on September 2, 2026. The gift was made to a third party, and no value was received. Following this transaction, he directly holds 4,416,873 shares of Lemonade common stock.
Lemonade, Inc. (LMND) reported that Chief Insurance Officer John Sheldon Peters sold 11,000 shares of common stock on 2026-08-13 in an open market or private transaction at a weighted average price of $52.55 per share, as described in a footnote. Following this sale, he directly holds 76,942 shares of Lemonade common stock. The transaction was not reported as made under a Rule 10b5-1 trading plan.
Peters John Sheldon reported acquisition or exercise transactions in this Form 4 filing.
Lemonade, Inc. reported that Chief Insurance Officer John Sheldon Peters received a grant of 10,000 restricted stock units (RSUs) on July 27, 2026. These RSUs vest in 16 equal quarterly installments beginning September 1, 2026, contingent on continued employment. Following this award, he directly holds 87,942 shares of common stock.
Lemonade, Inc. Chief Financial Officer Timothy E. Bixby reported an open-market sale of 73,000 shares of common stock on July 7, 2026 at a weighted average price of $79.18 per share. The transactions were executed under a pre-arranged Rule 10b5-1 trading plan adopted on March 13, 2026, meaning the sales were scheduled in advance. After these sales, Bixby directly holds 174,263 Lemonade shares. The filing notes the shares were sold in multiple trades between $76.03 and $81.13 per share.
Lemonade, Inc. Chief Insurance Officer John Sheldon Peters reported an open-market sale of common stock. On July 6, 2026, he sold 3,444 shares of Lemonade common stock at $79.00 per share. After this transaction, he directly holds 77,942 shares of common stock. The filing notes that this sale was made pursuant to a Rule 10b5-1 trading plan adopted on March 11, 2026, indicating the transaction was pre-scheduled rather than a discretionary trade.
Lemonade, Inc. director Michael A. Eisenberg reported a bona fide gift of 5,000 shares of common stock. The gift was made at a reported price of $0.00 per share and is a non-market transfer. After the gift, Eisenberg directly holds 195,452 common shares and has additional indirect interests through Aleph, L.P. and Aleph-Aleph, L.P., where he may share voting and investment power but disclaims beneficial ownership except for his pecuniary interest.
Lemonade, Inc. Chief Financial Officer Timothy E. Bixby reported a non-discretionary disposition of 2,227 shares of common stock on June 3, 2026 at $53.17 per share. According to the footnote, these shares were sold solely to cover tax withholding obligations tied to the vesting and settlement of Restricted Stock Units, rather than as a voluntary portfolio decision. After this transaction, Bixby directly holds 247,263 shares of Lemonade common stock.
Lemonade, Inc. Chief Insurance Officer John Sheldon Peters reported open-market sales of company common stock that were tied to equity compensation. He sold 1,735 shares on June 3 at $53.17 per share and 3,608 shares on June 4 at $52.94 per share, totaling 5,343 shares. After these transactions, he directly held 81,386 shares. A footnote explains that part of the activity represents shares sold to cover tax withholding obligations upon vesting of Restricted Stock Units and that sales were made pursuant to a Rule 10b5-1 trading plan, indicating these were pre-arranged, routine transactions rather than discretionary trades based on short-term market views.
Lemonade, Inc. insider Maya Prosor, Chief Business Officer, reported a small common stock transaction. On June 3, 2026, 1,220 shares of common stock were sold at $53.17 per share. According to the disclosure, this sale was not a discretionary transaction and reflects shares sold to cover tax withholding obligations tied to the vesting and settlement of Restricted Stock Units.
Following the sale, Prosor directly held 187,573 common shares, and indirectly held 29,286 common shares through Cohen Holdings, LLC, over which she has voting and dispositive control. The transaction represents a routine, tax-related disposition relative to her overall holdings.
Seeley Geoff reported acquisition or exercise transactions in this Form 4 filing.
Lemonade, Inc. director Geoff Seeley reported an equity award in the form of restricted stock units. He received 2,848 shares of common stock at no cash cost as a grant, increasing his direct holdings to 5,967 shares after the transaction.
The award consists of restricted stock units that vest and become exercisable on the earlier of the day immediately preceding the first annual meeting following the grant date or on June 3, 2027. Each unit represents a contingent right to receive one share of Lemonade’s common stock when it vests.
Ratanchandani Prashant reported acquisition or exercise transactions in this Form 4 filing.
Lemonade, Inc. director Prashant Ratanchandani received an equity award in the form of 2,848 restricted stock units (RSUs) of common stock at no cash cost. These RSUs will vest on the earlier of the day immediately preceding the first annual meeting after the grant date or June 3, 2027.
Each RSU represents a contingent right to receive one share of Lemonade’s common stock once vesting conditions are met. Following this grant, Ratanchandani’s direct holdings total 6,185 common shares, reflecting routine, compensation-related equity rather than an open-market purchase.
Schwartz Debra reported acquisition or exercise transactions in this Form 4 filing.
Lemonade, Inc. director Debra Schwartz received an equity grant in the form of restricted stock units. She was awarded 2,848 RSUs, each representing a contingent right to receive one share of Lemonade common stock at no cash cost per share.
According to the grant terms, these RSUs will vest and become exercisable on the earlier of the day immediately preceding the first annual meeting following the grant date or June 3, 2027. After this award, Schwartz’s direct holdings reported in this filing total 24,415 shares of common stock.
Haj-Yehia Samer reported acquisition or exercise transactions in this Form 4 filing.
Lemonade, Inc. director Samer Haj-Yehia received an equity award in the form of restricted stock units. The grant covers 2,848 shares of common stock at no purchase price, increasing his direct holdings to 27,187 shares after the award.
The restricted stock units will vest and become exercisable on the earlier of the day immediately preceding the first annual meeting following the grant date or June 3, 2027. Each unit represents a contingent right to receive one share of Lemonade’s common stock.
Angelidis-Smith Maria reported acquisition or exercise transactions in this Form 4 filing.
Lemonade, Inc. director Maria Angelidis-Smith reported a new equity award and updated her share holdings. She received an award of 2,848 restricted stock units of common stock for no cash payment. These units will vest on the earlier of the day immediately preceding the first annual meeting following the grant date or on June 3, 2027, and each unit represents one share of common stock.
After the award, she holds 17,744 shares of common stock directly and 38,944 shares indirectly through the Smith Family Trust, where she serves as co-trustee with voting and dispositive control over the trust’s shares.
Lemonade, Inc. director Maria Angelidis-Smith reported open-market purchases of company stock. On March 10, 2026, she bought 3,350 shares of common stock at $55.30 per share in her direct account, bringing her direct holdings to 14,896 shares.
On the same date, Smith Family Trust, for which she serves as co-trustee with voting and dispositive control, purchased an additional 5,390 shares at $55.70 per share, increasing that trust’s holdings to 38,944 shares. The amended Form 4 corrects the transaction code to reflect these were open-market purchases.
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.
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. 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. 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.
Lemonade, Inc. reported that Chief Insurance Officer John Sheldon Peters sold common stock in a planned transaction. On January 22, 2026, he sold 9,000 shares of common stock at $90 per share in an open market sale coded as a disposition. The transaction was executed under a Rule 10b5-1 trading plan adopted on August 22, 2025, indicating it was pre-arranged rather than opportunistic.
Following this sale, Peters beneficially owns 70,228 shares of Lemonade common stock, held directly. The filing shows no derivative securities activity in this period.
Lemonade, Inc. reported an insider equity transaction by Chief Insurance Officer John Sheldon Peters. On January 8, 2026, Peters exercised a stock option to acquire 18,457 shares of Lemonade common stock at an exercise price of $5.26 per share, reflected as a code "M" transaction. This exercise converted derivative securities (options) into common stock rather than representing an open-market purchase or sale.
After the transaction, Peters beneficially owned 79,228 shares of Lemonade common stock in direct form and held 10,000 stock options directly. The filing notes that the option involved in the transaction was fully vested and exercisable.
Lemonade, Inc. disclosed that Chief Insurance Officer John Peters sold shares of company stock. On January 6, 2026, he sold 10,000 shares of common stock at $80 per share in a planned transaction under a Rule 10b5-1 trading plan adopted on August 22, 2025. After this sale, he directly owned 60,771 shares of Lemonade common stock.
Lemonade, Inc. reported an insider stock sale by Chief Operating Officer Adina Eckstein. On December 11, 2025, Eckstein sold 7,919 shares of Lemonade common stock in an open market transaction coded as a sale. The shares were sold at a weighted average price of $84.15 per share, with the trade executed in multiple transactions at different prices.
The filing states that the sale was made pursuant to a Rule 10b5-1 trading plan adopted on September 8, 2025. After this transaction, Eckstein beneficially owned 188,391 shares of Lemonade common stock, held directly.
Lemonade, Inc. director Debra Schwartz reported selling 4,200 shares of common stock on 12/11/2025 at a weighted average price of $83.59 per share.
After this transaction, she beneficially owns 21,567 shares directly. The sale was executed through multiple trades, with individual prices ranging from $83.56 to $83.76.
Lemonade, Inc.’s Chief Operating Officer Adina Eckstein reported a sale of 7,919 shares of common stock on December 10, 2025. The transaction, coded as a sale, was carried out under a pre-arranged Rule 10b5-1 trading plan adopted on September 8, 2025, which is designed to allow insiders to trade according to a preset schedule. The weighted average price for the shares was $81.15 per share.
Following this transaction, Eckstein beneficially owns 196,310 shares of Lemonade common stock in direct ownership. The filing notes that the reported price reflects multiple trades and that full trade-by-trade pricing details are available on request.
Lemonade, Inc. reported an insider stock sale by its Chief Insurance Officer, John Peters. On 12/10/2025, he sold 3,554 shares of common stock at a price of $81 per share, in a transaction coded "S" for sale.
After this transaction, Peters beneficially owns 70,771 shares of Lemonade common stock, held directly. The filing is a routine Form 4 report of insider trading activity and does not describe any derivative securities transactions.
Lemonade, Inc.’s Chief Operating Officer, Adina Eckstein, reported multiple stock transactions in early December 2025. On December 8 and 9, 2025, she exercised employee stock options with exercise prices of $24.47 and $44.57 per share, converting them into Lemonade common stock. She also reported several open-market sales of common shares on those dates at prices ranging from about $77.17 to $78.97 per share.
After the reported transactions, Eckstein directly beneficially owned 204,229 shares of Lemonade common stock. The filing notes that the reported sales were made pursuant to a pre-arranged Rule 10b5-1 trading plan adopted on September 8, 2025. The derivative securities table shows the corresponding option exercises and the remaining stock options held following these transactions.
Lemonade, Inc. reported that its Chief Financial Officer, Timothy Bixby, sold 2,862 shares of common stock on 12/02/2025 at a price of $72.74 per share. According to the filing, the sale was not a discretionary trade, but shares sold to cover tax withholding obligations tied to the vesting and settlement of Restricted Stock Units. After this transaction, Bixby beneficially owned 251,625 Lemonade common shares directly.
Lemonade, Inc. insider activity: Chief Business Officer Maya Prosor reported a small sale of Lemonade common stock. On 12/02/2025, 198 shares of common stock were sold at a price of $72.74 per share. The filing explains that this sale was not a discretionary trade, but shares sold to cover tax withholding obligations tied to the vesting and settlement of Restricted Stock Units.
After this transaction, Prosor beneficially owns 7,627 shares directly and 29,286 shares indirectly through Cohen Holdings, LLC, over which she has voting and dispositive control. The form is filed as an individual Form 4 for one reporting person.
Lemonade, Inc. reported insider share sales by its Chief Insurance Officer, John Peters. On 12/02/2025, Peters sold 2,677 shares of common stock at $72.74 per share to cover tax withholding obligations tied to the vesting and settlement of Restricted Stock Units. On 12/03/2025, he sold an additional 2,667 shares at $72.37 per share under a Rule 10b5-1 trading plan, which is a pre-arranged program for trading company stock. After these transactions, Peters beneficially owned 74,325 shares of Lemonade common stock, held directly.
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.
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) reported an insider equity grant. Director Geoff Seeley acquired 3,119 shares of common stock on 10/07/2025 at a stated price of $0, reflecting an award of restricted stock units (RSUs).
The filing notes the RSU award will vest in three equal annual installments, and each RSU represents a right to receive one share of common stock. Following the reported transaction, beneficial ownership was 3,119 shares, held directly.
Lemonade, Inc. (LMND) disclosed a routine insider equity grant. Director Prashant Ratanchandani received 3,337 restricted stock units on 10/16/2025, reported as an acquisition at $0 per unit. Each RSU represents the right to receive one share of common stock and will vest in three equal annual installments.
Following this grant, the reporting person beneficially owned 3,337 shares directly, reflecting the awarded RSUs. The filing was signed by an attorney-in-fact on the reporting person’s behalf.