Lemonade officer sells shares to cover RSU taxes and 10b5-1 plan

Lemonade, Inc. reported insider share sales by its Chief Insurance Officer, John Peters.

Accepted by SEC EDGAR 12/04/2025 - 04:49 PM EST Learn about SEC filing dates

Rhea-AI Filing Summary

Lemonade, Inc. reported insider share sales by its Chief Insurance Officer, John Peters. On 12/02/2025, Peters sold 2,677 shares of common stock at $72.74 per share to cover tax withholding obligations tied to the vesting and settlement of Restricted Stock Units. On 12/03/2025, he sold an additional 2,667 shares at $72.37 per share under a Rule 10b5-1 trading plan, which is a pre-arranged program for trading company stock. After these transactions, Peters beneficially owned 74,325 shares of Lemonade common stock, held directly.

Insider Trade Summary

Net Seller: 5,344 shares

Net Sell 2 txns

Insider Peters John Sheldon

Role Chief Insurance Officer

Sold 5,344 shs ($388K)

Type	Security	Shares	Price	Value
Sale	COMMON STOCK	2,667	$72.37	$193K
Sale	COMMON STOCK	2,677	$72.74	$195K

Holdings After Transaction: COMMON STOCK — 74,325 shares (Direct)

Footnotes (2)

1. F1. The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.
2. F2. Represents sale pursuant to a Rule 10b5-1 trading plan.

FAQ

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

The filing reports that Chief Insurance Officer John Peters sold 2,677 Lemonade common shares on 12/02/2025 at $72.74 and 2,667 shares on 12/03/2025 at $72.37 per share.

Why did John Peters sell Lemonade (LMND) shares on 12/02/2025?

The filing states the 12/02/2025 sale of 2,677 shares was not a discretionary transaction and was made to cover tax withholding obligations related to vesting and settlement of Restricted Stock Units.

Was the 12/03/2025 Lemonade (LMND) share sale under a Rule 10b5-1 plan?

Yes. The sale of 2,667 shares on 12/03/2025 at $72.37 per share is described as being made pursuant to a Rule 10b5-1 trading plan.

How many Lemonade (LMND) shares does John Peters own after these transactions?

After the reported transactions, John Peters beneficially owns 74,325 shares of Lemonade common stock, held directly.

What is John Peters’ role at Lemonade (LMND)?

John Peters is identified as an officer of Lemonade, Inc., serving as the company’s Chief Insurance Officer.

Does this Form 4 for Lemonade (LMND) involve any derivative securities?

No derivative securities transactions are reported in Table II; only common stock sales are shown in Table I.

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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)
12/02/2025

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	12/02/2025		S(1)		2,677	D	$72.74	76,992	D
COMMON STOCK	12/03/2025		S(2)		2,667	D	$72.37	74,325	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

Explanation of Responses:

1. The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

2. Represents sale pursuant to a Rule 10b5-1 trading plan.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for John Peters	12/04/2025
	** 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.