Lemonade (NYSE: LMND) COO trades shares under Rule 10b5-1 stock plan

Rhea-AI Filing Summary

Lemonade, Inc.’s Chief Operating Officer, Adina Eckstein, reported multiple stock transactions in early December 2025. On December 8 and 9, 2025, she exercised employee stock options with exercise prices of $24.47 and $44.57 per share, converting them into Lemonade common stock. She also reported several open-market sales of common shares on those dates at prices ranging from about $77.17 to $78.97 per share.

After the reported transactions, Eckstein directly beneficially owned 204,229 shares of Lemonade common stock. The filing notes that the reported sales were made pursuant to a pre-arranged Rule 10b5-1 trading plan adopted on September 8, 2025. The derivative securities table shows the corresponding option exercises and the remaining stock options held following these 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

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

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

X

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^*

Eckstein Adina

(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 Operating Officer

3. Date of Earliest Transaction (Month/Day/Year)
12/08/2025

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	12/08/2025		M		16,250	A	$24.47	244,237	D
COMMON STOCK	12/08/2025		M		1,549	A	$44.57	245,786	D
COMMON STOCK	12/08/2025		S(1)		17,799	D	$78.97	227,987	D
COMMON STOCK	12/08/2025		S(1)		15,839	D	$78.92	212,148	D
COMMON STOCK	12/08/2025		S(1)		7,919	D	$78.94	204,229	D
COMMON STOCK	12/09/2025		M		29,237	A	$44.57	233,466	D
COMMON STOCK	12/09/2025		S(1)		29,237	D	$77.17	204,229	D

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
STOCK OPTION	$24.47	12/08/2025		M			16,250	(2)	06/06/2030	COMMON STOCK	16,250	$24.47	0	D
STOCK OPTION	$44.57	12/08/2025		M			1,549	(3)	12/06/2031	COMMON STOCK	1,549	$44.57	33,751	D
STOCK OPTION	$44.57	12/09/2025		M			29,237	(3)	12/06/2031	COMMON STOCK	29,237	$44.57	4,514	D

Explanation of Responses:

1. Represents sale pursuant to a Rule 10b5-1 trading plan, adopted September 8, 2025.

2. This stock option is fully vested.

3. The option began vesting and became exercisable in 16 equal quarterly installments beginning on March 6, 2022.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for Adina Eckstein	12/10/2025
	** 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).
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FAQ

What insider activity did Lemonade (LMND) disclose in this Form 4?

The Form 4 reports that Chief Operating Officer Adina Eckstein exercised employee stock options and sold Lemonade common shares in several transactions on December 8 and 9, 2025.

How many Lemonade (LMND) shares does the COO hold after these transactions?

Following the reported option exercises and sales, Adina Eckstein beneficially owned 204,229 shares of Lemonade, Inc. common stock in direct ownership.

At what prices did the Lemonade (LMND) COO exercise stock options?

The filing shows option exercises for common stock at exercise prices of $24.47 per share and $44.57 per share, converting options into Lemonade common shares.

At what prices were Lemonade (LMND) shares sold by the COO?

The reported sales of Lemonade common stock occurred at prices between approximately $77.17 and $78.97 per share across multiple transactions.

Were the Lemonade (LMND) insider sales part of a Rule 10b5-1 trading plan?

Yes. The explanation states that the reported sales represent sales pursuant to a Rule 10b5-1 trading plan that was adopted on September 8, 2025.

What happens to the stock options shown in the Lemonade (LMND) Form 4?

The derivative table shows option exercises that reduced certain option positions to zero and others with remaining balances, with one stock option noted as fully vested and another vesting in 16 equal quarterly installments beginning March 6, 2022.