Lemonade (LMND) Form 144 — Insider Sales Total $3.07M Recent Proceeds

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) Form 144 filed a notice to sell 2,906 common shares valued at $146,294.73 (based on the aggregate market value reported) with an approximate sale date of 09/03/2025. The shares were acquired on 08/29/2025 by restricted stock vesting from the issuer and were paid as compensation. The filing shows 73,916 common shares were sold by Timothy E. Bixby during the prior three months for aggregate gross proceeds of $3,072,290.92, with individual sales between 06/03/2025 and 07/21/2025. The filer certifies no undisclosed material adverse information and acknowledges legal penalties for misstatement.

Positive

• Shares to be sold were acquired via restricted stock vesting, indicating the disposal arises from compensation rather than an external purchase.
• Filer attests no undisclosed material adverse information, which is a standard assurance for Rule 144 notices.

Negative

• Insider sold 73,916 shares in the prior three months for approximately $3,072,290.92 in gross proceeds, reflecting substantial recent insider liquidity.
• Form does not state a 10b5-1 trading plan adoption date, so these sales cannot be confirmed as pre-authorized from this filing alone.

Insights

Securities Analyst

TL;DR: Insider sales are sizeable in aggregate but this filing reports a small, post-vesting sale tied to compensation.

The Form 144 shows a proposed sale of 2,906 shares acquired via restricted stock vesting and designated as compensation, scheduled for early September 2025. Insider Timothy E. Bixby sold 73,916 shares in the prior three months for roughly $3.07 million in gross proceeds, indicating active disposition of vested equity. From a market-impact perspective the single 2,906-share notice is immaterial relative to the issuer's outstanding shares (73,886,417 reported), but the recent cadence and total quantum of prior sales could influence investor perception of insider liquidity needs. This is a routine disclosure under Rule 144 rather than a corporate event affecting operations.

Corporate Governance Expert

TL;DR: The filing documents routine post-vesting sales; governance implications hinge on insider intent and any trading plans.

The transaction was sourced from restricted stock vesting and paid as compensation, which aligns with typical equity compensation programs. The filer attests no material nonpublic information, and no trading-plan adoption date is provided on the form. The recent sequence of sales by the same individual suggests regular liquidity actions rather than a one-off event. For governance assessment, absence of a stated 10b5-1 plan date in the filing means investors cannot confirm preauthorization of the trades from this document alone.

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	Fidelity Brokerage Services LLC 900 Salem Street Smithfield RI 02917	2906	146294.73	73886417	09/03/2025	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	08/29/2025	Restricted Stock Vesting	Issuer			2906	08/29/2025	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
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/03/2025	1916	67540.92
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/05/2025	5000	187500.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/09/2025	5000	201500.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/11/2025	6000	255000.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/16/2025	11000	460300.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/23/2025	11000	476960.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/30/2025	11000	469590.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York` NY 10013	Common	07/07/2025	11000	466400.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	07/14/2025	5000	190800.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	07/18/2025	6000	255000.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	07/21/2025	1000	42700.00

144: Remarks and Signature

Remarks

Date of Notice

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 Lemonade (LMND) Form 144 report?

The filing notifies a proposed sale of 2,906 common shares valued at $146,294.73, acquired on 08/29/2025 via restricted stock vesting and to be sold around 09/03/2025.

How many shares did the insider sell in the past three months and for how much?

Timothy E. Bixby sold 73,916 shares between 06/03/2025 and 07/21/2025, with aggregate gross proceeds of $3,072,290.92.

Were the shares being sold part of compensation for LMND?

Yes. The 2,906 shares were acquired on 08/29/2025 through restricted stock vesting and the payment nature is listed as compensation.

Does the Form 144 indicate any undisclosed material adverse information?

The filer represents by signature that they do not know any material adverse information about the issuer that has not been publicly disclosed.

Is there a stated 10b5-1 trading plan on this Form 144?

No adoption date for a 10b5-1 trading plan is provided on the filing, so preauthorization is not documented here.