LMND Form 4: COO exercises 45,988 options; holds 227,987 shares

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) reported insider activity by COO Adina Eckstein on Form 4. She exercised stock options at $27.35 and sold the resulting shares in open‑market transactions.

On Nov 7, 2025, she exercised 20,000 options and sold 20,000 shares at $72.04, then exercised another 20,000 and sold 20,000 at $74.00. On Nov 10, 2025, she exercised 5,988 options and sold 5,988 shares at $78.00. Following these transactions, she held 227,987 shares directly.

The exercised options carried a $27.35 exercise price, are noted as fully vested, and are listed with an expiration of Apr 5, 2032.

Insider Trade Summary

Exercise and Sale: 45,988 shares ($2.13M approx. pre-tax spread)

Exercise and Sale 8 txns

Insider Eckstein Adina

Role Chief Operating Officer

Sold 45,988 shs ($3.39M)

Approx. gross sale proceeds $3.39M

Approx. exercise cost $1.26M

Approx. pre-tax spread $2.13M

Type	Security	Shares	Price	Value
Exercise	STOCK OPTION	5,988	$27.35	$164K
Exercise	COMMON STOCK	5,988	$27.35	$164K
Sale	COMMON STOCK	5,988	$78.00	$467K
Exercise	STOCK OPTION	40,000	$27.35	$1.09M
Exercise	COMMON STOCK	20,000	$27.35	$547K
Sale	COMMON STOCK	20,000	$72.04	$1.44M
Exercise	COMMON STOCK	20,000	$27.35	$547K
Sale	COMMON STOCK	20,000	$74.00	$1.48M

Holdings After Transaction: STOCK OPTION — 7,074 shares (Direct); COMMON STOCK — 227,987 shares (Direct)

Footnotes (1)

1. F1. This stock option is fully vested.

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Form 4 Insider Transactions: What Each Field Means →

Accepted by SEC EDGAR 11/12/2025 - 04:58 PM Learn about SEC filing dates

FAQ

What did LMND’s COO report on the Form 4?

She exercised stock options at $27.35 and sold the resulting shares in market transactions on Nov 7, 2025 and Nov 10, 2025.

How many LMND shares were sold and at what prices?

She sold 20,000 at $72.04 and 20,000 at $74.00 on Nov 7, and 5,988 at $78.00 on Nov 10.

How many options were exercised and at what price?

She exercised 20,000 + 20,000 on Nov 7 and 5,988 on Nov 10, all at an exercise price of $27.35.

What is the COO’s direct share ownership after these trades?

Directly owned shares were 227,987 following the reported transactions.

What is the expiration date of the exercised option award?

The stock option is listed with an expiration date of Apr 5, 2032 and is noted as fully vested.

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)
11/07/2025

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	11/07/2025		M		20,000	A	$27.35	247,987	D
COMMON STOCK	11/07/2025		S		20,000	D	$72.04	227,987	D
COMMON STOCK	11/07/2025		M		20,000	A	$27.35	247,987	D
COMMON STOCK	11/07/2025		S		20,000	D	$74	227,987	D
COMMON STOCK	11/10/2025		M		5,988	A	$27.35	233,975	D
COMMON STOCK	11/10/2025		S		5,988	D	$78	227,987	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	$27.35	11/07/2025		M			40,000	(1)	04/05/2032	COMMON STOCK	40,000	$27.35	13,062	D
STOCK OPTION	$27.35	11/10/2025		M			5,988	(1)	04/05/2032	COMMON STOCK	5,988	$27.35	7,074	D

Explanation of Responses:

1. This stock option is fully vested.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for Adina Eckstein	11/12/2025
	** 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.