Adina Eckstein Files Form 4 — Sale Under 10b5-1 Plan; 21,250 Holdings

Rhea-AI Filing Summary

Adina Eckstein, Chief Operating Officer of Lemonade, Inc. (LMND), reported transactions on Form 4 dated 08/11/2025. The filing discloses a sale of common stock executed pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024, with a reported sale price of $53. Following the reported transactions, Ms. Eckstein beneficially owns 189,653 shares of common stock.

The filing also reports a derivative entry for a stock option with an exercise/conversion price of $24.47 covering 5,000 underlying shares and shows 21,250 derivative securities beneficially owned following the transactions; the option is stated to be fully vested. The form was signed by an attorney-in-fact on 08/13/2025.

Positive

• Transaction executed under a Rule 10b5-1 plan, which provides pre-established trade terms and reduces concerns about opportunistic timing.
• Clear disclosure of vested stock option (remark states the stock option is fully vested), improving transparency on executive compensation.
• Substantial retained ownership reported: 189,653 shares beneficially owned following the transactions.

Negative

• Insider sale reported (common stock sold at a reported price of $53), which investors may view as a reduction in insider holdings.
• Form shows option-related transactions that change derivative holdings to 21,250, which could affect potential dilution if exercised.

Insights

Corporate Governance Expert

TL;DR: Insider sale disclosed under a pre-established 10b5-1 plan reduces signaling risk; continued substantial ownership remains.

The filing shows the COO executed a sale under a Rule 10b5-1 plan adopted 12/05/2024, which generally limits opportunistic-timing concerns because trades follow a pre-set plan. The disclosure of continued direct beneficial ownership of 189,653 shares suggests the officer retains meaningful exposure to company performance. The stock option disclosure and the statement that it is fully vested provide transparency on executive compensation.

Securities Analyst

TL;DR: Transaction is a routine insider sale with option holdings disclosed; it is informational but not clearly materially adverse.

The Form 4 documents a sale at $53 and reports 21,250 derivative securities beneficially owned after the transactions, including a 5,000-option entry with a $24.47 exercise price. Because the sale was executed under a 10b5-1 plan, it indicates pre-planned liquidity rather than opportunistic insider timing. No additional corporate events or unusual disclosures appear in the filing.

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)
08/11/2025

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	08/11/2025		M		0	A	$24.47	189,653	D
COMMON STOCK	08/11/2025		S(1)		0	D	$53	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	08/11/2025		M			5,000	(2)	06/06/2030	COMMON STOCK	5,000	$24.47	21,250	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	08/13/2025
	** 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 did Adina Eckstein report on the Form 4 for LMND?

On 08/11/2025 Ms. Eckstein reported a sale of common stock executed under a Rule 10b5-1 plan and a derivative entry for a 5,000-option position; beneficial ownership following the transactions was 189,653 common shares and 21,250 derivative securities.

Was the sale made under a pre-established trading plan?

Yes. The filing states the sale represents a sale pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024.

What prices are reported in the Form 4?

The filing reports a sale price of $53 for the common stock and a derivative/exercise price of $24.47 for the stock option.

How many options and shares are shown in the filing?

The derivative table shows 5,000 underlying shares tied to a stock option and reports 21,250 derivative securities beneficially owned after the transactions; direct common stock beneficial ownership is 189,653 shares.

Who signed the Form 4 and when?

The form was signed by Timothy Bixby, Attorney-in-Fact for Adina Eckstein on 08/13/2025.