Sec Form 3 Filing - Prosor Maya @ Lemonade, Inc. - 2024-02-21

FORM 3 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

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, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Prosor Maya 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 Business Officer (Last) (First) (Middle) C/O LEMONADE, INC., 5 CROSBY STREET, 3RD FLOOR 3. Date of Earliest Transaction (MM/DD/YY) 02/21/2024 (Street) NEW YORK, NY10013 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 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 79,286 I ( 1 ) Directly held by Cohen Holdings, LLC COMMON STOCK 927 D COMMON STOCK 1,309 ( 2 ) 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 (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 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 (MM/DD/YY) 7. Title and Amount of Underlying Securities (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 of Derivative Security: 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 $ 23.69 ( 3 ) 12/01/2029 COMMON STOCK 80,000 D STOCK OPTION $ 18.17 ( 4 ) 02/07/2033 COMMON STOCK 100,000 D STOCK OPTION $ 27.35 ( 5 ) 04/05/2032 COMMON STOCK 49,800 D STOCK OPTION $ 15.13 ( 6 ) 08/11/2033 COMMON STOCK 83,700 D STOCK OPTION $ 79.3 ( 7 ) 09/02/2031 COMMON STOCK 28,500 D STOCK OPTION $ 19.03 ( 8 ) 07/14/2032 COMMON STOCK 65,000 D STOCK OPTION $ 44.57 ( 9 ) 12/06/2031 COMMON STOCK 14,800 D STOCK OPTION $ 94.07 ( 10 ) 03/10/2031 COMMON STOCK 5,000 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Prosor Maya C/O LEMONADE, INC. 5 CROSBY STREET, 3RD FLOOR NEW YORK, NY10013 Chief Business Officer Signatures /s/ Timothy Bixby, Attorney-in-Fact for Maya Prosor 03/04/2024 Signature of Reporting Person Date

Explanation of Responses:

( 1 )The Reporting Person is the owner of Cohen Holdings, LLC and has voting and dispositive control over the shares held by Cohen Holdings, LLC. ( 2 )This number represents restricted stock units that vest in 16 quarterly installments that began on September 1, 2021, subject to the Reporting Person's continued employment with the Issuer through each applicable vesting date. These 1,309 shares are the remaining restricted stock units to vest beginning on March 1, 2024. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock. ( 3 )The option is fully vested and exercisable. ( 4 )The options vest in 16 quarterly installments which began on December 1, 2022. The option is vested and exercisable as to 25,000 shares. ( 5 )The options vest in 16 quarterly installments which began on April 5, 2022. The option is vested and exercisable as to 21,791 shares. ( 6 )The options vest in 16 quarterly installments which began on August 7, 2023. The option is vested and exercisable as to 10,464 shares. ( 7 )The options vest in 16 quarterly installments which began on September 1, 2021. The option is vested and exercisable as to 16,033 shares. ( 8 )The options vest in 16 quarterly installments which began on July 14, 2022. The option is vested and exercisable as to 24,378 shares. ( 9 )The options vest in 16 quarterly installments which began on December 6, 2021. The option is vested and exercisable as to 7,400 shares. ( 10 )The options vest in 16 quarterly installments which began on March 10, 2021. The option is vested and exercisable as to 3,440 shares.

Remarks: Exhibit 24 - Power of Attorney.

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).

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