Adina Eckstein - 08 Mar 2026 Form 4 Insider Report for Lemonade, Inc. (LMND)

Role: Chief Operating Officer
Signature: /s/ Timothy Bixby, Attorney-in-Fact for Adina Eckstein
Issuer symbol: LMND
Transactions as of: 08 Mar 2026
Net transactions value: $0
Form type: 4
Filing time: 10 Mar 2026, 16:53:02 UTC
Previous filing: 15 Dec 2025
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
Eckstein Adina	Chief Operating Officer	C/O LEMONADE, INC., 5 CROSBY STREET, 3RD FLOOR, NEW YORK	/s/ Timothy Bixby, Attorney-in-Fact for Adina Eckstein	10 Mar 2026	0001874702

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	LMND	COMMON STOCK	Award		+145,112	+77%	$0.000000^*	333,503	08 Mar 2026	Direct	F1

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	LMND	STOCK OPTION	Award		+54,417		$0.000000^*	54,417	08 Mar 2026	COMMON STOCK	54,417	$55.13	Direct	F2

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	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.
F2	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.

Content

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.