[Form 4] Lemonade, Inc. Insider Trading Activity

Rhea-AI Filing Summary

John Sheldon Peters, Chief Insurance Officer of Lemonade, Inc. (LMND), was granted a stock option covering 25,556 shares with an exercise price of $59.74. The reported transaction date is 08/21/2025 and the Form 4 was filed on 08/25/2025. The option vests in 12 equal quarterly installments beginning 08/18/2025 and becomes exercisable according to that schedule, with an expiration date of 08/18/2035. After this grant, the reporting person directly beneficially owns 25,556 common shares (from this option) at a stated price of $0 for the reported beneficial ownership figure. The form was signed by an attorney-in-fact on behalf of the reporting person.

Positive

• Alignment of interests: Granting of stock options aligns the Chief Insurance Officer's compensation with shareholder value.
• Retention mechanics: Vesting over 12 quarterly installments supports executive retention through 2025–2028 vesting period.
• Timely disclosure: Form 4 was filed within days of the transaction date and signed by an authorized attorney-in-fact.

Negative

• Potential future dilution: The option covers 25,556 shares which will dilute shareholders if exercised.
• No cashless exercise details: The filing does not disclose whether alternative exercise or settlement methods will be available.

Insights

Financial Analyst

TL;DR: Routine equity compensation grant aligns executive incentives with shareholder value without immediate cash proceeds.

The Form 4 discloses a standard stock option grant of 25,556 shares to the Chief Insurance Officer at a $59.74 exercise price, vesting quarterly over three years starting 08/18/2025 and expiring 08/18/2035. This is a compensation event, not a sale, and does not change outstanding dilution until exercised. For investors, the grant signals continued executive retention incentives but has limited immediate impact on cash flow or share count until exercise.

Corporate Governance Expert

TL;DR: Standard grant with customary vesting schedule; procedural filing appears complete and timely.

The disclosure identifies the reporting person and relationship (Chief Insurance Officer) and shows the option will vest in 12 equal quarterly installments beginning 08/18/2025. The Form 4 is properly executed by an attorney-in-fact and filed within a few days of the transaction date, consistent with Section 16 reporting practice. There are no indications of accelerated vesting or special terms disclosed here.

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
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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)
08/21/2025

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

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	$59.74	08/21/2025		A		25,556		(1)	08/18/2035	COMMON STOCK	25,556	$0	25,556	D

Explanation of Responses:

1. The option will vest and become exercisable in 12 equal quarterly installments beginning on August 18, 2025, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for John Peters	08/25/2025
	** 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.

FAQ

What did John Peters (LMND) receive according to the Form 4?

He was granted a stock option covering 25,556 shares with an exercise price of $59.74 and an expiration date of 08/18/2035.

When does the option vest and become exercisable?

The option vests in 12 equal quarterly installments beginning on 08/18/2025; exercisability follows each vesting installment.

What is the reporting and filing date on the Form 4 for this transaction?

The transaction date is 08/21/2025 and the Form 4 was filed (signed) on 08/25/2025.

How many shares does the reporting person beneficially own after the grant?

The Form 4 reports 25,556 shares (from this option) as the amount beneficially owned following the reported transaction.

Who signed the Form 4?

The Form 4 was signed by Timothy Bixby, Attorney-in-Fact for John Peters on 08/25/2025.