LMND Officer Bixby Files $476K Stock Sale Notice|Lemonade Executive Plans 11K Share Disposal via Form 144|Form 144: LMND CFO Trading Activity Update

Rhea-AI Filing Summary

Form 144 filing reveals Lemonade officer Timothy E. Bixby plans to sell 11,000 shares of common stock valued at $476,960 through Fidelity Brokerage Services on NYSE. The shares were acquired via options granted on 12/01/2019. Bixby has been actively selling Lemonade shares in past 3 months, with six previous transactions totaling 27,916 shares for approximately $1.1 million in proceeds. Sales include: 5,000 shares on 3/24/25 ($187.5K), 1,916 shares on 6/3/25 ($67.5K), and multiple 5,000-6,000 share blocks between 6/5-6/16/25. The planned sale represents a small fraction of Lemonade's 73.27M outstanding shares. Filing indicates compliance with Rule 10b5-1 trading plan adopted 12/12/2024.

Positive

• The aggregate market value of shares to be sold ($476,960) represents only about 0.015% of total shares outstanding, indicating minimal dilution impact
• The sale appears to be part of a planned 10b5-1 trading program adopted in December 2024, suggesting orderly selling rather than reactive disposition

Negative

• Officer Timothy E. Bixby has sold significant amounts of stock over the past 3 months - approximately 27,916 shares worth over $1.1 million from March to June 2025
• The consistent selling pattern from a key executive (multiple sales in June 2025) could signal reduced confidence in future stock appreciation
• The latest proposed sale of 11,000 shares comes shortly after several other large dispositions, potentially indicating accelerated selling pressure

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	11000	476960.00	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	06/23/2025	Option Granted - 12/01/2019	Issuer			11000	06/23/2025	Cash

* 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	03/24/2025	5000	187500.00
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	5000	205300.00

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

How many LMND shares is Timothy Bixby selling on June 23, 2025?

Timothy Bixby, an officer of Lemonade, Inc., is selling 11,000 shares of common stock with an aggregate market value of $476,960.00 through Fidelity Brokerage Services LLC.

How many LMND shares has Timothy Bixby sold in the past 3 months before June 2025?

In the past 3 months, Timothy Bixby has sold a total of 27,916 shares: 5,000 shares on March 24, 1,916 shares on June 3, 5,000 shares on June 5, 5,000 shares on June 9, 6,000 shares on June 11, and 5,000 shares on June 16, 2025.

What is the total value of LMND stock Timothy Bixby sold in June 2025?

In June 2025 prior to this filing, Timothy Bixby sold LMND stock worth $916,840.92, comprising sales of $67,540.92 on June 3, $187,500 on June 5, $201,500 on June 9, $255,000 on June 11, and $205,300 on June 16.

When did Timothy Bixby acquire the LMND shares being sold in this Form 144?

The shares being sold were acquired through a stock option that was granted on December 1, 2019, with the acquisition date listed as June 23, 2025, when the option was exercised with a cash payment.

How many total shares of LMND were outstanding at the time of this Form 144 filing?

According to the Form 144 filing, Lemonade, Inc. had 73,266,170 shares outstanding at the time of the filing on June 23, 2025.