[Form 4] Lemonade, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Shai Wininger, President and Director of Lemonade, Inc. (LMND), received a grant of stock options covering 127,780 shares with an exercise price of $59.74. The option award was reported as a transaction dated 08/21/2025 and the form was signed on 08/25/2025 by an attorney-in-fact. The filing states the option will vest in 12 equal quarterly installments beginning on 08/18/2025, subject to continued employment, and the option expires on 08/18/2035. After the reported grant, the reporting person beneficially owns 127,780 shares directly attributable to this option position.

Positive

• Grant of 127,780 stock options to the reporting person is explicitly disclosed
• Clear vesting schedule: 12 equal quarterly installments beginning 08/18/2025
• Exercise price stated: $59.74 and expiration date provided (08/18/2035)

Negative

• None.

Insights

Financial Analyst

TL;DR: Routine executive equity grant aligns management with shareholders but is not a cash compensation event.

The filing documents a non-derivative equity grant in the form of a stock option for 127,780 shares at a $59.74 exercise price. Vesting begins 08/18/2025 over 12 quarterly installments, with an expiration date of 08/18/2035. This is a standard long-term incentive that ties the reporting persons compensation to future share performance. The transaction increases the reporting persons direct beneficial ownership by 127,780 options as reported.

Corporate Governance Expert

TL;DR: Grant to a President/Director is a common governance practice to promote retention and alignment.

The Form 4 confirms the recipient is both a director and the President, indicating the award is to a senior executive with governance responsibilities. The explicit vesting schedule—12 equal quarterly installments starting 08/18/2025—is a time-based retention schedule. The signature by an attorney-in-fact on 08/25/2025 completes the reporting requirements. The disclosure is clear and follows Section 16 reporting norms.

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^*

Wininger Shai

(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)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	President

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		127,780		(1)	08/18/2035	COMMON STOCK	127,780	$0	127,780	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 Shai Wininger	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

Who reported the transaction on Form 4 for LMND?

Shai Wininger, identified as President and Director, reported the transaction.

What security and amount were reported on the Form 4 for LMND?

Stock options covering 127,780 shares were reported as acquired.

What is the exercise price and key dates for the option grant reported?

Exercise price $59.74, vesting begins 08/18/2025 in 12 quarterly installments, expiration 08/18/2035, transaction dated 08/21/2025.

How many shares does the reporting person beneficially own after this transaction?

127,780 shares are reported as beneficially owned following the transaction.

Who signed the Form 4 and when was it filed?

Signed by Timothy Bixby, Attorney-in-Fact for Shai Wininger on 08/25/2025; transaction date 08/21/2025.