Lemonade CBO sells 1,040 shares for taxes

Lemonade’s chief business officer reported a tax-withholding sale of 1,040 LMND shares and continues to hold over 215,000 shares directly and indirectly.

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) reported that Chief Business Officer Maya Prosor had 1,040 shares of common stock sold on September 3, 2026 at $54.63 per share. A footnote states these shares were sold to cover tax withholding obligations from the vesting of Restricted Stock Units and were not a discretionary trade. After this transaction, she held 186,533 shares directly and 29,286 shares indirectly through Cohen Holdings, LLC, over which she has voting and dispositive control. No Rule 10b5-1 trading plan is reported.

Insider Trade Summary

Net Seller: 1,040 shares

Net Sell 2 txns

Insider Prosor Maya

Role Chief Business Officer

Sold 1,040 shs ($57K)

Type	Security	Shares	Price	Value
Sale	COMMON STOCK F1	1,040	$54.63	$57K
holding	COMMON STOCK F2	--	--	--

Holdings After Transaction: COMMON STOCK — 186,533 shares (Direct); COMMON STOCK — 29,286 shares (Indirect, Directly held by Cohen Holdings, LLC)

Footnotes (2)

1. F1. 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. F2. The Reporting Person is the owner of Cohen Holdings, LLC and has voting and dispositive control over the shares held by Cohen Holdings, LLC.

Key Figures

Shares sold: 1,040 shares Sale price: $54.63 per share Direct holdings after transaction: 186,533 shares +2 more

5 metrics

Shares sold 1,040 shares Common stock sold on September 3, 2026 to cover tax withholding

Sale price $54.63 per share Price for the 1,040 LMND common shares sold on September 3, 2026

Direct holdings after transaction 186,533 shares LMND common stock directly held by Maya Prosor after the sale

Indirect holdings after transaction 29,286 shares LMND common stock held indirectly through Cohen Holdings, LLC

Net buy/sell shares 1,040 shares net sold Net share change across reported non-derivative transactions in this Form 4

Key Terms

Restricted Stock Units, tax withholding obligations, voting and dispositive control

3 terms

Restricted Stock Units financial

"in connection with the vesting and settlement of Restricted Stock Units"

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

tax withholding obligations financial

"represents shares sold to cover tax withholding obligations"

voting and dispositive control financial

"has voting and dispositive control over the shares held"

FAQ

What insider transaction did LMND’s Chief Business Officer report?

Chief Business Officer Maya Prosor reported a sale of 1,040 LMND common shares on September 3, 2026 at $54.63 per share. The sale was made to cover tax withholding obligations from vesting Restricted Stock Units and was not a discretionary trade.

Why were 1,040 LMND shares sold in this Form 4?

The 1,040 shares were sold to cover tax withholding obligations related to the vesting and settlement of Restricted Stock Units. The filing states this was not a discretionary transaction by the reporting person.

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

After the reported sale, Maya Prosor holds 186,533 LMND shares directly and 29,286 shares indirectly through Cohen Holdings, LLC, over which she has voting and dispositive control.

Was the LMND insider sale under a Rule 10b5-1 trading plan?

No. The filing’s Rule 10b5-1 checkbox is unchecked and no footnote describes a trading plan, so no Rule 10b5-1 plan is reported for this transaction.

What is Cohen Holdings, LLC’s role in LMND share ownership?

29,286 LMND shares are held indirectly through Cohen Holdings, LLC. The filing states that Maya Prosor is the owner of Cohen Holdings, LLC and has voting and dispositive control over those shares.

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Available on EDGAR 09/08/2026 - 05:37 PM Accepted by SEC EDGAR 09/08/2026 - 05:36 PM Learn about SEC filing dates

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 NEW YORK 10013

(City) (State) (Zip)

UNITED STATES

(Country)

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
09/03/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

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	09/03/2026		S(1)		1,040	D	$54.63	186,533	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	09/08/2026
	** 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.
* Form 4: SEC 1474 (03-26)