[Form 4] Lemonade, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Lemonade, Inc. insider Maya Prosor, Chief Business Officer, reported a small common stock transaction. On June 3, 2026, 1,220 shares of common stock were sold at $53.17 per share. According to the disclosure, this sale was not a discretionary transaction and reflects shares sold to cover tax withholding obligations tied to the vesting and settlement of Restricted Stock Units.

Following the sale, Prosor directly held 187,573 common shares, and indirectly held 29,286 common shares through Cohen Holdings, LLC, over which she has voting and dispositive control. The transaction represents a routine, tax-related disposition relative to her overall holdings.

Insider Trade Summary

Net Seller: 1,220 shares ($64,867)

Net Sell 2 txns

Insider Prosor Maya

Role Chief Business Officer

Sold 1,220 shs ($65K)

Type	Security	Shares	Price	Value
Sale	COMMON STOCK	1,220	$53.17	$65K
holding	COMMON STOCK	--	--	--

Holdings After Transaction: COMMON STOCK — 187,573 shares (Direct, null); 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.

Key Figures

Shares sold: 1,220 shares Sale price: $53.17 per share Direct holdings after: 187,573 shares +2 more

5 metrics

Shares sold 1,220 shares Common stock sold on June 3, 2026

Sale price $53.17 per share Price for 1,220 common shares sold

Direct holdings after 187,573 shares Direct common stock held after transaction

Indirect holdings after 29,286 shares Common stock held via Cohen Holdings, LLC after transaction

Net shares sold 1,220 shares Net sell direction per transaction summary

Key Terms

Restricted Stock Units, tax withholding obligations, voting and dispositive control, open-market sale

4 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 in connection with the vesting"

voting and dispositive control financial

"has voting and dispositive control over the shares held by Cohen Holdings, LLC."

open-market sale financial

"transaction_action": "open-market sale""

An open-market sale is when a shareholder sells existing shares directly on a public exchange to any willing buyer, rather than through a private deal. Think of it like putting goods on a busy market stall where price is set by supply and demand; for investors it matters because such sales increase available supply, can put short-term downward pressure on the stock price, and signal changes in liquidity or investor confidence.

See more from StockTitan in Google Search and AI answers. Adds StockTitan as a preferred source · opens Google

Add on Google Not now

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 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)
06/03/2026

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	06/03/2026		S(1)		1,220	D	$53.17	187,573	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	06/05/2026
	** 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.
* Form 4: SEC 1474 (03-26)

FAQ

What did Lemonade (LMND) insider Maya Prosor report in this Form 4?

Maya Prosor reported the sale of 1,220 Lemonade common shares at $53.17 each. The filing explains the sale covered tax withholding from vested Restricted Stock Units and was not a discretionary trade, indicating a routine tax-related transaction rather than an independent portfolio decision.

Was the Lemonade (LMND) insider sale by Maya Prosor a discretionary transaction?

No, the filing states the sale was not a discretionary transaction by Maya Prosor. The 1,220 shares were sold solely to satisfy tax withholding obligations arising from the vesting and settlement of Restricted Stock Units, characterizing it as a routine administrative sale.

How many Lemonade (LMND) shares does Maya Prosor hold after this Form 4 transaction?

After the transaction, Maya Prosor directly holds 187,573 Lemonade common shares. She also indirectly holds 29,286 shares through Cohen Holdings, LLC, where she has voting and dispositive control, leaving her with a substantial remaining equity position following this small tax-related sale.

At what price were the Lemonade (LMND) shares sold in Maya Prosor’s Form 4 filing?

The 1,220 Lemonade common shares were sold at $53.17 per share. The filing clarifies that these shares were sold to cover tax withholding obligations connected to Restricted Stock Unit vesting, rather than as a discretionary open-market sale based on investment views.

What role does Cohen Holdings, LLC play in Maya Prosor’s Lemonade (LMND) ownership?

Cohen Holdings, LLC holds 29,286 Lemonade common shares for which Maya Prosor has voting and dispositive control. The filing notes she owns Cohen Holdings, LLC, so these indirectly held shares are included in her overall Lemonade ownership position in addition to her direct holdings.

What is the nature of the Restricted Stock Unit vesting mentioned in the Lemonade (LMND) Form 4?

The filing explains that the reported sale was made to cover tax withholding obligations from the vesting and settlement of Restricted Stock Units. When RSUs vest, taxes are due, and companies often sell a portion of shares to satisfy these obligations automatically.