Lemonade (LMND) insider plans sale of 18,930 shares per Form 144

A shareholder of Lemonade, Inc. (LMND) has filed a Form 144 notice to potentially sell 18,930 shares of common stock through Fidelity Brokerage Services LLC on the NYSE.

Rhea-AI Filing Summary

A shareholder of Lemonade, Inc. (LMND) has filed a Form 144 notice to potentially sell 18,930 shares of common stock through Fidelity Brokerage Services LLC on the NYSE. The filing lists an aggregate market value of about $1,377,536.10 for these shares, with 74,731,027 shares of common stock shown as outstanding and an approximate sale date of 11/20/2025. The shares to be sold were acquired mainly through restricted stock vesting and a stock option exercise between 2023 and 2024. Over the past three months, the same seller, John S. Peters, previously sold 2,718 shares of common stock for gross proceeds of $136,830.37, according to this notice.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What does the LMND Form 144 filing disclose?

The Form 144 filing for Lemonade, Inc. (LMND) discloses a shareholder’s intent to potentially sell 18,930 shares of common stock on the NYSE through Fidelity Brokerage Services LLC.

How many Lemonade (LMND) shares are covered by this Form 144 and what is their value?

The notice covers 18,930 common shares of Lemonade with an aggregate market value of about $1,377,536.10, as stated in the filing.

When might the LMND shares under this Form 144 be sold and on which exchange?

The filing lists an approximate sale date of 11/20/2025 and identifies the NYSE as the securities exchange for the potential sale of the 18,930 shares.

How were the LMND shares in the Form 144 acquired by the seller?

According to the acquisition table, the shares were obtained through restricted stock vesting on several dates in 2023 and 2024, and via a stock option exercise on 01/25/2024, including 9,000 shares acquired for cash.

How many Lemonade (LMND) shares are shown as outstanding in the Form 144?

The Form 144 lists 74,731,027 common shares outstanding in the securities information table.

Has the LMND shareholder sold any shares in the last three months?

Yes. The filing states that John S. Peters sold 2,718 shares of LMND common stock on 09/03/2025, receiving gross proceeds of $136,830.37.

Which broker is handling the potential LMND Form 144 sale?

The broker named in the Form 144 is Fidelity Brokerage Services LLC, located at 900 Salem Street, Smithfield, RI 02917.

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Accepted by SEC EDGAR 11/20/2025 - 10:19 AM Learn about SEC filing dates

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK	0001816299
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	Lemonade, Inc.
SEC File Number	001-39367
Address of Issuer	5 CROSBY STREET 3RD FLOOR NEW YORK NEW YORK 10013
Phone	(844) 733-8666
Name of Person for Whose Account the Securities are To Be Sold	Peters John Sheldon
See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.
Relationship to Issuer	Officer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common	Fidelity Brokerage Services LLC 900 Salem Street Smithfield RI 02917	18930	1377536.10	74731027	11/20/2025	NYSE

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	03/01/2023	Restricted Stock Vesting	Issuer			1212	03/01/2023	Compensation
Common	06/01/2023	Restricted Stock Vesting	Issuer			1337	06/01/2023	Compensation
Common	09/01/2023	Restricted Stock Vesting	Issuer			1308	09/01/2023	Compensation
Common	12/01/2023	Restricted Stock Vesting	Issuer			1988	12/01/2023	Compensation
Common	01/25/2024	Stock Option Exercise	Issuer			9000	01/25/2024	Cash
Common	03/01/2024	Restricted Stock Vesting	Issuer			2002	03/01/2024	Compensation
Common	06/01/2024	Restricted Stock Vesting	Issuer			2083	06/01/2024	Compensation

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	09/03/2025	2718	136830.37

144: Remarks and Signature

Remarks
Date of Notice	11/20/2025
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	08/22/2025
ATTENTION:
The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.
Signature	/s/ Daniel Tucci, as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for John S. Peters
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)