Lemonade (LMND) Chief Business Officer reports small tax-related stock sale

Rhea-AI Filing Summary

Lemonade, Inc. insider activity: Chief Business Officer Maya Prosor reported a small sale of Lemonade common stock. On 12/02/2025, 198 shares of common stock were sold at a price of $72.74 per share. The filing explains that this sale was not a discretionary trade, but shares sold to cover tax withholding obligations tied to the vesting and settlement of Restricted Stock Units.

After this transaction, Prosor beneficially owns 7,627 shares directly and 29,286 shares indirectly through Cohen Holdings, LLC, over which she has voting and dispositive control. The form is filed as an individual Form 4 for one reporting person.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Prosor Maya

(Last) (First) (Middle)

C/O LEMONADE, INC.

5 CROSBY STREET, 3RD FLOOR

(Street)

NEW YORK NY 10013

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Lemonade, Inc. [ LMND ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Business Officer

3. Date of Earliest Transaction (Month/Day/Year)
12/02/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
COMMON STOCK	12/02/2025		S(1)		198	D	$72.74	7,627	D
COMMON STOCK								29,286	I(2)	Directly held by Cohen Holdings, LLC

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

2. The Reporting Person is the owner of Cohen Holdings, LLC and has voting and dispositive control over the shares held by Cohen Holdings, LLC.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for Maya Prosor	12/04/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What insider transaction did Lemonade (LMND) report in this Form 4?

The Chief Business Officer, Maya Prosor, reported selling 198 shares of Lemonade common stock on 12/02/2025 at $72.74 per share.

Why did Maya Prosor sell Lemonade (LMND) shares?

The filing states the sale was not discretionary and represents shares sold to cover tax withholding obligations related to the vesting and settlement of Restricted Stock Units.

How many Lemonade (LMND) shares does Maya Prosor own after this transaction?

After the transaction, Maya Prosor directly owns 7,627 shares of Lemonade common stock and indirectly owns 29,286 shares through Cohen Holdings, LLC.

What is Cohen Holdings, LLC in relation to Lemonade (LMND) shares?

Cohen Holdings, LLC holds 29,286 shares of Lemonade common stock, and the filing states that Maya Prosor is the owner and has voting and dispositive control over these shares.

What is Maya Prosor’s role at Lemonade (LMND)?

Maya Prosor is reported as an Officer of Lemonade, Inc., holding the title of Chief Business Officer.

Is this Lemonade (LMND) Form 4 filed by multiple insiders?

No. The document indicates it is a Form filed by one reporting person, covering only the transactions and holdings of Maya Prosor.