Lemonade (NYSE: LMND) president granted 820,000 RSUs and 180,000 PRSUs

Rhea-AI Filing Summary

Wininger Shai reported acquisition or exercise transactions in this Form 4 filing.

Lemonade, Inc. president and director Shai Wininger reported two stock awards of common shares as compensation. He received an award of 820,000 restricted stock units, granted at a price of $0.0000 per share, increasing his direct holdings to 4,238,749 shares after that award and 4,418,749 shares after a second award.

The 820,000 restricted stock units vest quarterly over 8 years beginning on June 1, 2026, with 5% vesting during the first year, then 10%, 15%, 20%, 20%, 15%, 10% and 5% in subsequent years, subject to continued employment. He also received 180,000 performance restricted stock units that vest only if the company’s stock sustains a $110 closing price for at least 30 consecutive trading days within 24 months of the grant date. Each unit represents a contingent right to one share of common stock.

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

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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 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)

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
03/18/2026

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	03/18/2026		A		820,000(1)	A	$0	4,238,749	D
COMMON STOCK	03/18/2026		A		180,000(2)	A	$0	4,418,749	D

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. Represents an award of restricted stock units ("RSUs"), which will vest in quarterly installments over 8 years, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date. The RSU begins vesting quarterly on June 1, 2026 with 5% of the award vesting during the first year, 10% during the second year, 15% during the third year, 20% during each of the fourth and fifth years, 15% during the sixth year, 10% during the seventh year and 5% during the eighth year. Each RSU represents a contingent right to receive one share of the Issuer's common stock.

2. Represents an award of performance restricted stock units, which will vest if and only if the Company's stock price sustains a closing price of $110 for at least 30 consecutive trading days within 24 months of the Grant Date.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for Shai Wininger	03/20/2026
	** 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 insider transaction did Lemonade (LMND) president Shai Wininger report?

Shai Wininger reported two stock awards of Lemonade common shares. He received 820,000 restricted stock units and 180,000 performance restricted stock units as compensation grants at a stated price of $0.0000 per share.

How many Lemonade (LMND) shares does Shai Wininger hold after this Form 4?

After the reported awards, Shai Wininger directly holds 4,418,749 shares of Lemonade common stock. The first 820,000-unit award brought his holdings to 4,238,749 shares, and the second 180,000-unit grant increased them to 4,418,749 shares.

How do Shai Wininger’s 820,000 Lemonade RSUs vest over time?

The 820,000 restricted stock units vest quarterly over 8 years starting June 1, 2026. Vesting is 5% in year one, then 10%, 15%, 20%, 20%, 15%, 10% and 5%, contingent on his continued employment with Lemonade.

What conditions apply to Shai Wininger’s 180,000 Lemonade performance RSUs?

The 180,000 performance restricted stock units vest only if Lemonade’s stock price sustains a $110 closing price for at least 30 consecutive trading days within 24 months of the grant date, creating a clear performance hurdle for these shares.

Are Shai Wininger’s reported Lemonade transactions open-market purchases or sales?

The reported transactions are compensation-related stock awards, not open-market trades. Both entries use transaction code A, described as a grant, award or other acquisition, at a transaction price of $0.0000 per share.