Adina Eckstein - 08 Dec 2025 Form 4 Insider Report for Lemonade, Inc. (LMND)

Signature
/s/ Timothy Bixby, Attorney-in-Fact for Adina Eckstein
Issuer symbol
LMND
Transactions as of
08 Dec 2025
Net transactions value
-$5,536,946
Form type
4
Filing time
10 Dec 2025, 17:56:53 UTC
Previous filing
12 Nov 2025
Next filing
11 Dec 2025

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 Dec 2025 0001874702

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction LMND COMMON STOCK Options Exercise $397,638 +16,250 +7.1% $24.47 244,237 08 Dec 2025 Direct
transaction LMND COMMON STOCK Options Exercise $69,039 +1,549 +0.63% $44.57 245,786 08 Dec 2025 Direct
transaction LMND COMMON STOCK Sale $1,405,587 -17,799 -7.2% $78.97 227,987 08 Dec 2025 Direct F1
transaction LMND COMMON STOCK Sale $1,250,014 -15,839 -6.9% $78.92 212,148 08 Dec 2025 Direct F1
transaction LMND COMMON STOCK Sale $625,126 -7,919 -3.7% $78.94 204,229 08 Dec 2025 Direct F1
transaction LMND COMMON STOCK Options Exercise $1,303,093 +29,237 +14% $44.57 233,466 09 Dec 2025 Direct
transaction LMND COMMON STOCK Sale $2,256,219 -29,237 -13% $77.17 204,229 09 Dec 2025 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 Options Exercise $397,638 -16,250 -100% $24.47 0 08 Dec 2025 COMMON STOCK 16,250 $24.47 Direct F2
transaction LMND STOCK OPTION Options Exercise $69,039 -1,549 -4.4% $44.57 33,751 08 Dec 2025 COMMON STOCK 1,549 $44.57 Direct F3
transaction LMND STOCK OPTION Options Exercise $1,303,093 -29,237 -87% $44.57 4,514 09 Dec 2025 COMMON STOCK 29,237 $44.57 Direct F3
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Buy Plan / Sale Plan: These are also open market purchases/sales of shares, but in this case the transaction is part of a trading plan. Rule 10b5-1 allows insiders to setup a trading plan to buy/sell stocks over a certain period of time. Since the purchases/sales are predetermined, this protects the insiders from violating insider trading law.

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).

Explanation of Responses:

Id Content
F1 Represents sale pursuant to a Rule 10b5-1 trading plan, adopted September 8, 2025.
F2 This stock option is fully vested.
F3 The option began vesting and became exercisable in 16 equal quarterly installments beginning on March 6, 2022.