Lemonade officer exercises 18,457 stock options

Lemonade, Inc. reported an insider equity transaction by Chief Insurance Officer John Sheldon Peters.

Rhea-AI Filing Summary

Lemonade, Inc. reported an insider equity transaction by Chief Insurance Officer John Sheldon Peters. On January 8, 2026, Peters exercised a stock option to acquire 18,457 shares of Lemonade common stock at an exercise price of $5.26 per share, reflected as a code "M" transaction. This exercise converted derivative securities (options) into common stock rather than representing an open-market purchase or sale.

After the transaction, Peters beneficially owned 79,228 shares of Lemonade common stock in direct form and held 10,000 stock options directly. The filing notes that the option involved in the transaction was fully vested and exercisable.

Insider Trade Summary

18,457 shares exercised/converted

Exercise 2 txns

Insider Peters John Sheldon

Role Chief Insurance Officer

Type	Security	Shares	Price	Value
Exercise	STOCK OPTION	18,457	$5.26	$97K
Exercise	COMMON STOCK	18,457	$5.26	$97K

Holdings After Transaction: STOCK OPTION — 10,000 contracts (Direct); COMMON STOCK — 79,228 shares (Direct)

Footnotes (1)

1. F1. The option is fully vested and exercisable.

FAQ

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

What insider transaction did Lemonade (LMND) report in this Form 4?

The filing shows that Chief Insurance Officer John Sheldon Peters exercised a stock option (code "M") on January 8, 2026 to acquire 18,457 shares of Lemonade common stock at $5.26 per share.

Did the Lemonade (LMND) insider buy or sell shares on the market?

The reported transaction is an option exercise (code "M"), where stock options were converted into 18,457 shares of common stock. The entry does not describe an open-market sale or purchase.

How many Lemonade (LMND) shares does John Sheldon Peters own after this transaction?

Following the option exercise, John Sheldon Peters beneficially owned 79,228 shares of Lemonade common stock directly, according to the filing.

What was the exercise price of the Lemonade (LMND) stock options?

The stock option exercised on January 8, 2026 had an exercise price of $5.26 per share for 18,457 underlying common shares.

How many Lemonade (LMND) stock options does the insider hold after the transaction?

After this transaction, the filing reports that John Sheldon Peters directly held 10,000 stock options in Lemonade.

What is the position of the reporting person at Lemonade (LMND)?

The reporting person, John Sheldon Peters, is identified as Lemonade’s Chief Insurance Officer and is an officer but not a director or 10% owner.

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

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Accepted by SEC EDGAR 01/13/2026 - 02:22 PM 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).

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)
01/08/2026

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	01/08/2026		M		18,457	A	$5.26	79,228	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	01/08/2026		M			18,457	(1)	03/27/2028	COMMON STOCK	18,457	$5.26	10,000	D

Explanation of Responses:

1. The option is fully vested and exercisable.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for John Peters	01/13/2026
	** 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.