Adina Eckstein - Nov 7, 2025 Form 4 Insider Report for Lemonade, Inc. (LMND)

Signature
/s/ Timothy Bixby, Attorney-in-Fact for Adina Eckstein
Stock symbol
LMND
Transactions as of
Nov 7, 2025
Transactions value $
-$3,387,864
Form type
4
Date filed
11/12/2025, 04:58 PM
Previous filing
Aug 25, 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 2025-11-12 0001874702

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction LMND COMMON STOCK Options Exercise $547K +20K +8.77% $27.35 248K Nov 7, 2025 Direct
transaction LMND COMMON STOCK Sale -$1.44M -20K -8.06% $72.04 228K Nov 7, 2025 Direct
transaction LMND COMMON STOCK Options Exercise $547K +20K +8.77% $27.35 248K Nov 7, 2025 Direct
transaction LMND COMMON STOCK Sale -$1.48M -20K -8.06% $74.00 228K Nov 7, 2025 Direct
transaction LMND COMMON STOCK Options Exercise $164K +5.99K +2.63% $27.35 234K Nov 10, 2025 Direct
transaction LMND COMMON STOCK Sale -$467K -5.99K -2.56% $78.00 228K Nov 10, 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 -$1.09M -40K -75.38% $27.35 13.1K Nov 7, 2025 COMMON STOCK 40K $27.35 Direct F1
transaction LMND STOCK OPTION Options Exercise -$164K -5.99K -45.84% $27.35 7.07K Nov 10, 2025 COMMON STOCK 5.99K $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.