[Form 4] Lemonade, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Maya Prosor, Chief Business Officer of Lemonade, Inc. (LMND), reported a non-discretionary sale of 282 shares of Lemonade common stock on 09/03/2025 at a reported price of $50.34 per share to cover tax withholding related to the vesting and settlement of restricted stock units. After the transaction, Prosor directly beneficially owns 7,825 shares and indirectly owns 29,286 shares through Cohen Holdings, LLC, of which she is the owner and retains voting and dispositive control. The Form 4 was signed by an attorney-in-fact on 09/05/2025.

Insights

Financial Analyst

TL;DR: Routine, small-scale insider sale to cover tax obligations; no material change to insider stake.

The disclosed transaction is a limited non-discretionary sale of 282 shares at $50.34 to satisfy tax withholding from RSU vesting. The remaining direct and indirect holdings (7,825 and 29,286 shares) indicate continuing economic exposure to the company. This filing documents compliance with Section 16 reporting requirements and provides transparency on an executive's modest liquidity action rather than a strategic divestiture.

Corporate Governance Expert

TL;DR: Properly documented insider disposition tied to compensation settlement; governance processes appear followed.

The Form 4 explains the sale was not discretionary and was executed to cover tax withholding arising from RSU settlement, and identifies indirect ownership via Cohen Holdings, LLC with control retained by the reporting person. The timely filing and explanatory remarks align with standard governance and disclosure expectations for executive equity transactions.

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

OMB APPROVAL

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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)
09/03/2025

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	09/03/2025		S(1)		282	D	$50.34	7,825	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	09/05/2025
	** 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.
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