[Form 4] Lemonade, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Maya Prosor, Chief Business Officer of Lemonade, Inc. (LMND), was granted stock options totaling 76,668 shares on 08/21/2025. The options have an exercise price of $59.74 and expire on 08/18/2035. The filing reports that the option will vest in 12 equal quarterly installments beginning on 08/18/2025, subject to the reporting person remaining employed through each vesting date.

The Form 4 shows the reporting person directly beneficially owns 76,668 shares following the transaction. The document is signed by Timothy Bixby as attorney-in-fact for Maya Prosor and dated 08/25/2025.

Positive

• Grant disclosed: 76,668 stock options reported on Form 4
• Clear terms: $59.74 exercise price and 08/18/2035 expiration stated
• Vesting schedule provided: 12 equal quarterly installments starting 08/18/2025
• Direct ownership reported: 76,668 common shares beneficially owned following transaction

Negative

• None.

Insights

Corporate Governance Expert

TL;DR: Routine officer equity grant with time-based vesting to retain an executive.

The filing documents a standard equity compensation event: a grant of 76,668 stock options to the Chief Business Officer at a $59.74 exercise price, exercisable over 12 quarterly vesting periods beginning 08/18/2025 and expiring 08/18/2035. This structure ties long-term potential upside to continued employment. The disclosure is straightforward and contains the necessary vesting schedule and expiration information for investor transparency.

Compensation Analyst

TL;DR: Clear disclosure of grant size, strike, vesting cadence, and expiration—useful for assessing dilution and incentive alignment.

The data provided—76,668 options, $59.74 strike, 12 equal quarterly vesting installments starting 08/18/2025, and 08/18/2035 expiration—allows calculation of potential dilution and incentive timing. The report indicates direct beneficial ownership of 76,668 shares post-transaction, which aligns with a typical executive option award documented on a Form 4.

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^*

Prosor Maya

(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 Business 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		76,668		(1)	08/18/2035	COMMON STOCK	76,668	$0	76,668	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 Maya Prosor	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 Maya Prosor (LMND) receive according to the Form 4?

The Form 4 shows Maya Prosor was granted 76,668 stock options on 08/21/2025.

What is the exercise price and expiration date of the options reported for LMND?

The options have an exercise price of $59.74 and expire on 08/18/2035.

When do the options for LMND become exercisable?

The options vest in 12 equal quarterly installments beginning 08/18/2025, subject to continued employment.

How many shares does Maya Prosor beneficially own after the reported transaction?

The Form 4 reports 76,668 shares beneficially owned following the transaction.

Who signed the Form 4 filing for Maya Prosor and when?

The filing is signed by Timothy Bixby, Attorney-in-Fact for Maya Prosor and dated 08/25/2025.