Adina Eckstein - 07 Nov 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
07 Nov 2025
Net transactions value
-$3,387,864
Form type
4
Filing time
12 Nov 2025, 16:58:44 UTC
Previous filing
25 Aug 2025
Next filing
10 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 12 Nov 2025 0001874702

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction LMND COMMON STOCK Options Exercise $547,000 +20,000 +8.8% $27.35 247,987 07 Nov 2025 Direct
transaction LMND COMMON STOCK Sale $1,440,800 -20,000 -8.1% $72.04 227,987 07 Nov 2025 Direct
transaction LMND COMMON STOCK Options Exercise $547,000 +20,000 +8.8% $27.35 247,987 07 Nov 2025 Direct
transaction LMND COMMON STOCK Sale $1,480,000 -20,000 -8.1% $74.00 227,987 07 Nov 2025 Direct
transaction LMND COMMON STOCK Options Exercise $163,772 +5,988 +2.6% $27.35 233,975 10 Nov 2025 Direct
transaction LMND COMMON STOCK Sale $467,064 -5,988 -2.6% $78.00 227,987 10 Nov 2025 Direct

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 $1,094,000 -40,000 -75% $27.35 13,062 07 Nov 2025 COMMON STOCK 40,000 $27.35 Direct F1
transaction LMND STOCK OPTION Options Exercise $163,772 -5,988 -46% $27.35 7,074 10 Nov 2025 COMMON STOCK 5,988 $27.35 Direct F1
* 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 This stock option is fully vested.