Lemonade insider files Rule 144 to sell 5,000 shares on NYSE

Rhea-AI Filing Summary

The Form 144 filed for Lemonade, Inc. (LMND) reports a proposed sale of 5,000 common shares through Oppenheimer & Co. on the NYSE with an aggregate market value of $272,950. The shares were acquired on 06/07/2020 under an employee stock option plan and are to be paid in cash upon exercise on 08/13/2025. Outstanding shares are listed as 73,886,417, so the proposed sale equals roughly 0.0068% of outstanding stock. The filing also discloses three prior sales by the same person totaling 15,000 shares for $735,000 on 06/23/2025, 08/05/2025, and 08/11/2025. Signature and notice date fields are not shown in the provided content.

Insights

Securities Analyst

TL;DR: Routine insider option exercise and sale; transaction size is immaterial relative to outstanding shares and unlikely to move the market.

The Form 144 documents a proposed sale of 5,000 common shares valued at $272,950 via Oppenheimer on the NYSE. Relative to the 73,886,417 shares outstanding, this represents approximately 0.0068%, which is negligible for market impact. The seller also disclosed three recent sales totaling 15,000 shares for $735,000, indicating prior monetizations of option-derived holdings. The securities were acquired under an employee stock option plan and are to be paid in cash upon exercise, reducing uncertainty about payment method.

Corporate Governance Expert

TL;DR: The filing shows compliance with Rule 144 disclosure requirements, but the provided content lacks visible signature and notice date fields.

The notice includes standard Rule 144 representations and identifies the acquisition source as the issuer via an employee stock option plan. The broker and exchange are disclosed as Oppenheimer & Co. and NYSE. However, the provided extract does not display a completed signature block or a notice date, limiting confirmation of filing completion from the content alone. Multiple recent sales by the same person are disclosed and are transparent in amount and timing.

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	272950.00	73886417	08/13/2025	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	06/07/2020	Employee Stock Option Plan	Issuer			5000	08/13/2025	Cash - Upon exercise

* 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
Eckstein Adina 5 CROSBY STREET New York NY 10013	Common	06/23/2025	5000	225000.00
Eckstein Adina 5 CROSBY STREET New York NY 10013	Common	08/05/2025	5000	245000.00
Eckstein Adina 5 CROSBY STREET New York NY 10013	Common	08/11/2025	5000	265000.00

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

What does the LMND Form 144 disclose?

The form discloses a proposed sale of 5,000 common shares valued at $272,950, to be sold on the NYSE through Oppenheimer & Co. on 08/13/2025.

When and how were the shares being sold acquired?

The shares were acquired on 06/07/2020 under an Employee Stock Option Plan and the payment is listed as cash upon exercise on 08/13/2025.

How many shares has this person sold in the past three months and for how much?

The filing lists three sales totaling 15,000 shares with gross proceeds of $735,000 on 06/23/2025, 08/05/2025, and 08/11/2025.

What percentage of outstanding shares does the proposed sale represent?

With 5,000 shares proposed and 73,886,417 shares outstanding, the sale is approximately 0.0068% of outstanding shares.

Does the provided filing extract include the filer signature and notice date?

No. The provided content includes the standard representation language but does not show a completed signature block or a notice date.