[Form 4] Lemonade, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Lemonade, Inc. insider sale to cover tax withholding on vested RSUs. John Sheldon Peters, Chief Insurance Officer, reported a non-discretionary sale of 2,718 shares of Lemonade common stock on 09/03/2025 at a price of $50.34 per share to satisfy tax withholding obligations tied to the vesting and settlement of Restricted Stock Units. After the transaction he beneficially owned 102,397 shares. The Form 4 was signed by an attorney-in-fact on behalf of the reporting person on 09/05/2025. The filing states the sale was not discretionary and solely to cover taxes.

Insights

Securities Analyst

TL;DR: Routine, nondiscretionary tax-withholding sale of vested RSUs by an officer; not material on its own.

The reported transaction is a common administrative sale where 2,718 shares were disposed at $50.34 to satisfy tax withholding from RSU vesting. Such transactions typically do not signal a change in insider confidence or company fundamentals because the filer clarifies it was non-discretionary. Post-transaction ownership of 102,397 shares leaves the officer still materially positioned but without additional context on total outstanding shares or recent pattern of insider activity, this single Form 4 is neutral for valuation models.

Corporate Governance Expert

TL;DR: Administrative sale consistent with standard governance practices; disclosure is complete and timely.

The Form 4 discloses the nature of the sale as non-discretionary and related to tax withholding upon RSU settlement, which aligns with accepted compliance practices under Section 16. The filing includes transaction date, price, amount sold, and resulting beneficial ownership, and it was signed by an authorized attorney-in-fact. There are no indications of rule exceptions or atypical disposal methods in the submission.

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

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OMB Number:			3235-0287
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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)
09/03/2025

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	09/03/2025		S(1)		2,718	D	$50.34	102,397	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.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for John Peters	09/05/2025
	** 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 insider transaction did John S. Peters report for LMND?

The Form 4 reports a sale of 2,718 shares of Lemonade common stock on 09/03/2025 at $50.34 per share.

Why were the LMND shares sold by the reporting person?

The filing states the sale was not discretionary and was made to cover tax withholding obligations from the vesting and settlement of Restricted Stock Units.

How many LMND shares does the reporting person own after the sale?

After the reported transaction the reporting person beneficially owned 102,397 shares.

Who signed the Form 4 for John Peters?

The Form 4 was signed by /s/ Timothy Bixby, Attorney-in-Fact for John Peters on 09/05/2025.

Does this Form 4 indicate any discretionary insider selling?

No. The filing explicitly states the reported sale was not a discretionary transaction and was to meet tax withholding related to RSU vesting.