Tax-withholding share sale by Lemonade (LMND) chief business officer

Rhea-AI Filing Summary

Lemonade, Inc.'s Chief Business Officer, Maya Prosor, reported a non‑discretionary sale of 223 shares of common stock on March 3, 2026, at $50.12 per share. The shares were sold to cover tax withholding obligations tied to vesting and settlement of restricted stock units.

After this transaction, Prosor directly holds 7,404 common shares and indirectly holds 29,286 common shares through Cohen Holdings, LLC, over which she has voting and dispositive control.

Insider Trade Summary

Net Seller: 223 shares ($11,177)

Net Sell 2 txns

Insider Prosor Maya

Role Chief Business Officer

Sold 223 shs ($11K)

Type	Security	Shares	Price	Value
Sale	COMMON STOCK	223	$50.12	$11K
holding	COMMON STOCK	--	--	--

Holdings After Transaction: COMMON STOCK — 7,404 shares (Direct); COMMON STOCK — 29,286 shares (Indirect, Directly held by Cohen Holdings, LLC)

Footnotes (1)

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. The Reporting Person is the owner of Cohen Holdings, LLC and has voting and dispositive control over the shares held by Cohen Holdings, LLC.

Form 4 Insider Transactions: What Each Field Means →

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)
03/03/2026

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	03/03/2026		S(1)		223	D	$50.12	7,404	D
COMMON STOCK								29,286	I(2)	Directly held by Cohen Holdings, LLC

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. The Reporting Person is the owner of Cohen Holdings, LLC and has voting and dispositive control over the shares held by Cohen Holdings, LLC.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for Maya Prosor	03/05/2026
	** 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 Lemonade (LMND) executive Maya Prosor report in this Form 4?

Maya Prosor reported selling 223 Lemonade common shares in a non-discretionary transaction. The sale was executed on March 3, 2026, to cover tax withholding obligations from vesting restricted stock units, rather than as an elective share sale for portfolio or liquidity reasons.

At what price and on what date did Maya Prosor sell Lemonade (LMND) shares?

She sold 223 Lemonade common shares on March 3, 2026, at $50.12 per share. This open-market sale was specifically to satisfy tax withholding requirements arising from the vesting and settlement of her restricted stock unit awards, according to the filing footnote.

Was the Lemonade (LMND) share sale by Maya Prosor discretionary?

No, the sale was not discretionary by Maya Prosor. The filing states the 223 shares were sold solely to cover tax withholding obligations associated with vesting and settlement of restricted stock units, indicating it was a tax-related administrative transaction rather than a voluntary share disposal.

How many Lemonade (LMND) shares does Maya Prosor hold after this transaction?

Following the transaction, she directly holds 7,404 common shares of Lemonade. In addition, 29,286 common shares are held indirectly through Cohen Holdings, LLC, an entity she owns and over which she has voting and dispositive control, consolidating her beneficial ownership position.

What is Cohen Holdings, LLC’s role in Maya Prosor’s Lemonade (LMND) holdings?

Cohen Holdings, LLC holds 29,286 Lemonade common shares on an indirect basis for Maya Prosor. She is the owner of Cohen Holdings, LLC and has voting and dispositive control over those shares, meaning she effectively controls how those indirectly held shares are voted and potentially sold.