Lemonade Insider Stock Sale: What This $221K Transaction Signals for Investors

Rhea-AI Filing Summary

A Form 144 has been filed for Lemonade indicating a proposed sale of 5,000 shares of common stock with an aggregate market value of $221,550. The securities are to be sold through Oppenheimer & Co. Inc. on the NYSE, with an approximate sale date of June 23, 2025.

The shares were originally acquired through an Employee Stock Option Plan on December 24, 2019, with the filer receiving 20,000 shares from the issuer. Payment is to be made in cash upon execution of the sale.

Key details:

• Current shares outstanding: 73,266,170
• Sale price per share: approximately $44.31
• No other securities were sold by the filer during the past 3 months
• Transaction to be executed on the NYSE

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

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

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

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	Oppenheimer & Co. Inc. 85 Broad St. New York NY 10004	5000	221550.00	73266170	06/23/2025	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	12/24/2019	Employee Stock Option Plan	Issuer			20000	06/23/2025	Cash - Upon execution

* 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

Nothing to Report

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

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

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

How many LMND shares are being sold according to the Form 144 filed on June 28, 2025?

According to the Form 144 filing, 5,000 shares of LMND common stock are proposed to be sold through Oppenheimer & Co. Inc.

What is the aggregate market value of LMND shares being sold in this Form 144?

The aggregate market value of the LMND shares proposed to be sold is $221,550.00.

How did the LMND insider acquire these shares being sold?

The shares were originally acquired through an Employee Stock Option Plan from the issuer on December 24, 2019, with a total of 20,000 shares acquired at that time.

What is the total number of outstanding LMND shares according to the Form 144?

According to the Form 144 filing, Lemonade has 73,266,170 shares outstanding.

When is the approximate date of sale for the LMND shares mentioned in the Form 144?

The approximate date of sale for the LMND shares is listed as June 23, 2025.