Lemonade (LMND) COO receives multi-year RSU and stock option awards

Rhea-AI Filing Summary

Lemonade, Inc. Chief Operating Officer Adina Eckstein received two equity awards. She was granted 145,112 shares of common stock as restricted stock units and 54,417 stock options with an exercise price of $55.13 per share. After the grant, she directly holds 333,503 common shares. Both the RSUs and options vest quarterly over eight years, beginning in June 2026, with smaller portions vesting in early years and larger portions in years three to five. These awards are compensation grants rather than open-market purchases or sales.

Insider Trade Summary

2 transactions reported

Mixed 2 txns

Insider Eckstein Adina

Role Chief Operating Officer

Type	Security	Shares	Price	Value
Grant/Award	STOCK OPTION	54,417	$0.00	--
Grant/Award	COMMON STOCK	145,112	$0.00	--

Holdings After Transaction: STOCK OPTION — 54,417 shares (Direct); COMMON STOCK — 333,503 shares (Direct)

Footnotes (1)

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 begin 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. Represents an option award, which will vest and become exercisable in quarterly installments over 8 years, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date. The awards begin vesting quarterly on June 8, 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 option represents a contingent right to receive one share of the Issuer's common stock.

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^*

Eckstein Adina

(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 Operating Officer

3. Date of Earliest Transaction (Month/Day/Year)
03/08/2026

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	03/08/2026		A		145,112(1)	A	$0	333,503	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
STOCK OPTION	$55.13	03/08/2026		A		54,417		(2)	03/08/2036	COMMON STOCK	54,417	$0	54,417	D

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 begin 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 option award, which will vest and become exercisable in quarterly installments over 8 years, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date. The awards begin vesting quarterly on June 8, 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 option represents a contingent right to receive one share of the Issuer's common stock.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for Adina Eckstein	03/10/2026
	** 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) COO Adina Eckstein report in this Form 4?

Adina Eckstein reported receiving equity compensation: 145,112 restricted stock units and 54,417 stock options. These are grants from Lemonade, Inc., not market trades, and increase her direct equity exposure to 333,503 common shares following the transactions.

How do the new RSU awards for Lemonade (LMND) COO vest?

The 145,112 RSUs vest quarterly over eight years starting on June 1, 2026. Vesting is 5% in year one, 10% in year two, 15% in year three, 20% in years four and five, 15% in year six, 10% in year seven, and 5% in year eight.

What are the terms of the new stock options granted to Lemonade (LMND) COO?

Eckstein received 54,417 stock options with a $55.13 exercise price, expiring in 2036. The options vest quarterly over eight years beginning June 8, 2026, following the same 5%-10%-15%-20%-20%-15%-10%-5% annual vesting pattern described in the filing.

Are Adina Eckstein’s Lemonade (LMND) equity transactions open-market buys or sells?

The reported transactions are grants of RSUs and stock options, recorded under code “A” for awards or other acquisitions. They are compensation awards from the company, not open-market purchases or sales, and therefore do not represent trading decisions in the open market.

How many Lemonade (LMND) shares does the COO hold after these grants?

Following the grant of 145,112 common shares as RSUs, the filing states that Adina Eckstein directly owns 333,503 common shares. This figure reflects her reported direct holdings in Lemonade, Inc. common stock after the award transactions recorded on March 8, 2026.

When do the new Lemonade (LMND) COO equity awards start vesting?

The RSUs begin vesting on June 1, 2026, and the stock options begin vesting on June 8, 2026. Both vest quarterly over eight years, subject to her continued employment through each scheduled vesting date as disclosed in the footnotes.