[Form 4] Lemonade, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Timothy E. Bixby, Chief Financial Officer of Lemonade, Inc. (LMND), was granted a stock option on 08/21/2025 for 127,780 shares with an exercise price of $59.74 per share. The option vests in 12 equal quarterly installments beginning on 08/18/2025 and expires on 08/18/2035. The report indicates the shares underlying the option total 127,780 common shares and are listed as directly beneficially owned following the transaction. Vesting is conditioned on the reporting person’s continued employment through each vesting date. The Form 4 is signed by Mr. Bixby on 08/25/2025.

Insights

Securities Analyst

TL;DR: A sizable CFO option grant was reported, standard for executive compensation but potentially dilutive depending on company share count.

The Form 4 discloses an option award of 127,780 shares at a $59.74 exercise price, vesting quarterly over three years starting 08/18/2025 and expiring 08/18/2035. From a capital-markets perspective this appears to be a compensation award intended to align the CFO with long-term shareholder value. The filing does not disclose total outstanding shares or the grant’s accounting treatment, so the direct dilution impact and expense recognition cannot be assessed from this document alone. No other transactions or dispositions were reported.

Executive Compensation Specialist

TL;DR: Grant structure is typical: multi-year vesting and a 10-year option term to incent retention and performance.

The award vests in 12 equal quarterly installments beginning shortly before the first vesting date, which implies roughly three years of service-based vesting. A $59.74 strike and ten-year contractual term are conventional for option grants. The filing confirms vesting is conditioned on continued employment but does not attach performance conditions or forfeiture provisions beyond that. Absent company-wide grant policy details, this appears to be a routine but material executive equity award.

SEC Form 4

FORM 4

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
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a 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). See Instruction 10.

1. Name and Address of Reporting Person^*

BIXBY TIMOTHY E

(Last) (First) (Middle)

C/O LEMONADE, INC.

5 CROSBY STREET, 3RD FLOOR

(Street)

NEW YORK NY 10013

(City) (State) (Zip)

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 Financial Officer

3. Date of Earliest Transaction (Month/Day/Year)
08/21/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	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

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 (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	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 (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (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: 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	$59.74	08/21/2025		A		127,780		(1)	08/18/2035	COMMON STOCK	127,780	$0	127,780	D

Explanation of Responses:

1. The option will vest and become exercisable in 12 equal quarterly installments beginning on August 18, 2025, subject to the Reporting Person's continued employment with the. Issuer through each applicable vesting date.

Remarks:

	/s/ Timothy Bixby	08/25/2025
	** Signature of Reporting Person	Date
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).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What transaction did Timothy Bixby report on Form 4 for LMND?

The Form 4 reports an option grant of 127,780 shares with an exercise price of $59.74 granted on 08/21/2025.

When does the option granted to the CFO vest and expire?

The option vests in 12 equal quarterly installments beginning 08/18/2025 and expires on 08/18/2035.

Is the reported ownership direct or indirect?

The filing lists the post-transaction ownership as direct (D) for the 127,780 underlying common shares.

Does the Form 4 indicate any performance conditions for vesting?

No performance conditions are disclosed; the explanation states vesting is subject to the reporting person’s continued employment through each vesting date.

When was the Form 4 signed by the reporting person?

The Form 4 is signed by Timothy Bixby on 08/25/2025.