Lemonade officer plans sale of 2,249 shares

An officer of Lemonade, Inc. filed a Rule 144 notice to sell 2,249 shares of LMND common stock acquired via restricted stock vesting.

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) has a notice of proposed sale of securities filed on behalf of officer John S. Peters under Rule 144. The notice covers 2,249 shares of common stock to be sold through Fidelity Brokerage Services LLC, acquired via restricted stock vesting on September 1, 2026 as compensation.

The filing also lists prior sales of Lemonade common stock by John S. Peters over the preceding three months, including multiple transactions between June and September 2026 with stated share counts and dollar amounts.

Key Figures

Shares to be sold under Rule 144: 2,249 shares Aggregate market value of current notice shares: $122,458.05 Shares acquired via restricted stock vesting: 2,249 shares +3 more

6 metrics

Shares to be sold under Rule 144 2,249 shares Common stock to be sold by John S. Peters under the current notice

Aggregate market value of current notice shares $122,458.05 Value of 2,249 shares of Lemonade common stock in the current filing

Shares acquired via restricted stock vesting 2,249 shares Acquired on September 1, 2026 from issuer as compensation

Shares sold June 4, 2026 3,608 shares Prior sale of Lemonade common stock by John S. Peters

Proceeds June 4, 2026 sale $191,007.52 Amount for 3,608 shares sold June 4, 2026

Largest single prior sale in past 3 months 11,000 shares for $578,000.38 Sale on August 13, 2026 by John S. Peters

Key Terms

Rule 144, Restricted Stock Vesting, attorney-in-fact

3 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144."

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

Restricted Stock Vesting financial

"Common | 09/01/2026 | Restricted Stock Vesting | Issuer"

Restricted stock vesting is the timetable and conditions under which shares granted to employees or insiders become fully owned and can be sold, typically requiring continued work or meeting performance goals. It matters to investors because large blocks of shares can become tradable at once, which can change share supply and price, and because vesting aligns insiders’ incentives with the company’s long‑term performance—think of it like a timed unlock that both rewards and locks in key people.

attorney-in-fact regulatory

"as attorney-in-fact for John S. Peters"

An attorney-in-fact is the person or entity given legal authority through a power of attorney to act on behalf of another for specific tasks, such as signing documents, voting shares, or handling transactions. For investors, this matters because it lets a trusted representative make timely decisions or complete paperwork when the owner cannot, much like handing keys to someone to run errands on your behalf—so checks on scope and limits of that authority are important.

FAQ

What does the Form 144 filing disclose for Lemonade, Inc. (LMND)?

It discloses that officer John S. Peters intends to sell 2,249 shares of Lemonade, Inc. common stock under Rule 144, with the shares acquired as restricted stock vesting on September 1, 2026 and to be sold through Fidelity Brokerage Services LLC.

How many LMND shares are covered by this new Rule 144 notice?

The notice covers 2,249 shares of Lemonade, Inc. common stock. These shares were acquired on September 1, 2026 through restricted stock vesting from the issuer as compensation.

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

The filing lists an aggregate market value of $122,458.05 for the 2,249 shares of Lemonade, Inc. common stock to be sold through Fidelity Brokerage Services LLC on the NYSE.

What prior LMND share sales by John S. Peters are disclosed?

The filing lists prior sales of Lemonade common stock: 3,608 shares for $191,007.52 on June 4, 2026; 3,444 shares for $272,076.00 on July 6, 2026; 11,000 shares for $578,000.38 on August 13, 2026; and 859 shares for $46,928.03 on September 3, 2026.

Who is executing the LMND share sale under this Form 144?

The sale is to be executed through Fidelity Brokerage Services LLC. The notice is signed by Jennifer Ruchti as a duly authorized representative of Fidelity Brokerage Services LLC, acting as attorney-in-fact for John S. Peters.

On which market are the LMND shares to be sold according to the filing?

The filing states that the Lemonade, Inc. common stock covered by the notice is to be sold on the NYSE, with 2,249 shares having an aggregate market value of $122,458.05 at the time referenced.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Available on EDGAR 09/04/2026 - 11:46 AM Accepted by SEC EDGAR 09/04/2026 - 11:45 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	2249	122458.05	77396615	09/04/2026	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	09/01/2026	Restricted Stock Vesting	Issuer			2249	09/01/2026	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	06/04/2026	3608	191007.52
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	07/06/2026	3444	272076.00
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	08/13/2026	11000	578000.38
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	09/03/2026	859	46928.03

144: Remarks and Signature

Remarks
Date of Notice	09/04/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	03/12/2026
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/ Jennifer Ruchti, 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)