Lemonade Insurance Chief Sells $294K in Stock After 755% Price Gain

Lemonade Chief Insurance Officer John Peters executed significant stock transactions on June 23, 2025, as reported in this Form 4 filing.

Rhea-AI Filing Summary

Lemonade Chief Insurance Officer John Peters executed significant stock transactions on June 23, 2025, as reported in this Form 4 filing. The transactions involved:

• Exercise of stock options for 6,543 shares at $5.26 per share
• Immediate sale of all 6,543 shares at $45.00 per share under a pre-established Rule 10b5-1 trading plan from August 30, 2024

Following these transactions, Peters retains 106,115 shares of common stock held directly, plus 28,457 vested stock options. The options have an exercise price of $5.26 and expire on March 27, 2028. This transaction pattern of exercising options and selling shares was executed according to a predetermined trading plan, suggesting planned portfolio management rather than a reactive market decision.

Insider Trade Summary

Exercise and Sale: 6,543 shares ($260K approx. pre-tax spread)

Exercise and Sale 3 txns

Insider Peters John Sheldon

Role Chief Insurance Officer

Sold 6,543 shs ($294K)

Approx. gross sale proceeds $294K

Approx. exercise cost $34K

Approx. pre-tax spread $260K

Type	Security	Shares	Price	Value
Exercise	STOCK OPTION	6,543	$5.26	$34K
Exercise	COMMON STOCK	6,543	$5.26	$34K
Sale	COMMON STOCK	6,543	$45.00	$294K

Holdings After Transaction: STOCK OPTION — 28,457 contracts (Direct); COMMON STOCK — 106,115 shares (Direct)

Footnotes (2)

1. F1. Represents sale pursuant to a Rule 10b5-1 trading plan adopted August 30, 2024.
2. F2. The stock option is fully vested.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

How many LMND shares did Chief Insurance Officer John Peters sell on June 23, 2025?

John Peters sold 6,543 shares of LMND common stock on June 23, 2025 at a price of $45 per share. This sale was executed pursuant to a Rule 10b5-1 trading plan adopted on August 30, 2024.

What was the exercise price of LMND stock options exercised by John Peters?

John Peters exercised stock options with a strike price of $5.26 per share. He exercised 6,543 options which were fully vested, with an original expiration date of March 27, 2028.

How many LMND shares does John Peters own after his June 2025 transactions?

After the reported transactions, John Peters directly owns 106,115 shares of LMND common stock and 28,457 stock options. The transactions involved exercising 6,543 options and immediately selling the resulting shares.

What type of trading plan did LMND's Chief Insurance Officer use for his stock sale?

The stock sale was executed pursuant to a Rule 10b5-1 trading plan that John Peters adopted on August 30, 2024. Rule 10b5-1 plans are pre-established trading plans that help insiders avoid allegations of insider trading.

AI-generated analysis. How Rhea-AI works. Not financial advice.

Form 4 Insider Transactions: What Each Field Means →

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Accepted by SEC EDGAR 06/25/2025 - 11:56 AM Learn about SEC filing dates

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^*

Peters John Sheldon

(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 Insurance Officer

3. Date of Earliest Transaction (Month/Day/Year)
06/23/2025

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	06/23/2025		M		6,543	A	$5.26	112,658	D
COMMON STOCK	06/23/2025		S(1)		6,543	D	$45	106,115	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	$5.26	06/23/2025		M			6,543	(2)	03/27/2028	COMMON STOCK	6,543	$5.26	28,457	D

Explanation of Responses:

1. Represents sale pursuant to a Rule 10b5-1 trading plan adopted August 30, 2024.

2. The stock option is fully vested.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for John Peters	06/25/2025
	** 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.