Lemonade COO executes option exercise and planned 10b5-1 sale of 5,000 shares

Rhea-AI Filing Summary

Adina Eckstein, Chief Operating Officer of Lemonade, Inc. (LMND), reported option exercise and a contemporaneous sale on 08/13/2025. She exercised 5,000 stock options at an exercise price of $24.47 and immediately sold 5,000 common shares at $58.00 per share pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024. The option exercised is fully vested. After these transactions, Ms. Eckstein beneficially owned 189,653 shares. The Form 4 was signed by an attorney-in-fact on her behalf on 08/15/2025.

Insights

Securities Analyst

TL;DR: Routine insider option exercise and planned sale under a 10b5-1 plan; no net change in reported beneficial holdings.

Ms. Eckstein exercised 5,000 options at $24.47 and sold 5,000 shares at $58.00 on the same date, consistent with a pre-established Rule 10b5-1 plan adopted December 5, 2024. The exercise is fully vested and the post-transaction beneficial ownership remains 189,653 shares, indicating the sale likely monetized the exercised position rather than materially reducing long-term ownership. For investors, this is a compliance-driven liquidity action rather than an unexpected disposition.

Corporate Governance Specialist

TL;DR: Transaction reflects governance best practices by using a documented 10b5-1 plan and proper disclosure.

The filing discloses that the sale was executed pursuant to a 10b5-1 trading plan adopted on December 5, 2024, which provides an affirmative defense to insider trading claims. The Form 4 includes the required details: transaction codes, exercise price, sale price, and confirmation that the option was fully vested. This presentation aligns with transparent reporting standards expected of officers who transact in company stock.

Insider Trade Summary

Net Seller: 5,000 shares ($290,000)

Net Sell 3 txns

Insider Eckstein Adina

Role Chief Operating Officer

Sold 5,000 shs ($290K)

Type	Security	Shares	Price	Value
Exercise	STOCK OPTION	5,000	$24.47	$122K
Exercise	COMMON STOCK	5,000	$24.47	$122K
Sale	COMMON STOCK	5,000	$58.00	$290K

Holdings After Transaction: STOCK OPTION — 16,250 shares (Direct); COMMON STOCK — 189,653 shares (Direct)

Footnotes (1)

1. Represents sale pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024. The stock option is fully vested.

Form 4 Insider Transactions: What Each Field Means →

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)
08/13/2025

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	08/13/2025		M		5,000	A	$24.47	189,653	D
COMMON STOCK	08/13/2025		S(1)		5,000	D	$58	189,653	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	08/13/2025		M			5,000	(2)	06/06/2030	COMMON STOCK	5,000	$24.47	16,250	D

Explanation of Responses:

1. Represents sale pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024.

2. The stock option is fully vested.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for Adina Eckstein	08/15/2025
	** 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).
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