[Form 4] Lemonade, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Timothy E. Bixby, Chief Financial Officer and Director of Lemonade, Inc. (LMND), reported a non-discretionary sale of 2,906 shares of Lemonade common stock on 09/03/2025 at a price of $50.34 per share to cover tax withholding obligations arising from the vesting and settlement of restricted stock units. After the transaction he beneficially owned 260,487 shares directly and 30,000 shares indirectly through the Timothy E Bixby Family Trust, for which he is co-trustee with voting and dispositive control. The Form 4 is signed and dated 09/05/2025.

Positive

• Sale was disclosed as non-discretionary and reported on Form 4 with a signed filing date of 09/05/2025
• Transaction reason provided: shares sold to cover tax withholding related to RSU vesting
• Significant retained ownership: 260,487 shares directly plus 30,000 shares indirectly via family trust

Negative

• None.

Insights

Financial Analyst

TL;DR: Routine tax-withholding sale; modest reduction in shares owned, no indication of change in role or strategy.

The reported sale of 2,906 shares at $50.34 was described as non-discretionary and executed to satisfy tax withholding on vested restricted stock units. This is a common liquidity event for executives and does not, by itself, indicate a change in conviction about the company. Post-transaction beneficial ownership remains sizable at 260,487 shares directly plus 30,000 indirectly via a family trust, preserving ongoing alignment with shareholders.

Corporate Governance Expert

TL;DR: Disclosure is consistent with Section 16 reporting; trust holdings and co-trustee control are clearly stated.

The Form 4 discloses the reporting person's relationship to the issuer (CFO and Director) and specifies indirect ownership via the Timothy E Bixby Family Trust with co-trustee control. The filing includes an explanation that the sale was to cover tax withholding from RSU settlement, which clarifies the nature of the transaction and supports transparency under insider reporting rules.

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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hours per response:			0.5

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)
09/03/2025

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
COMMON STOCK	09/03/2025		S(1)		2,906	D	$50.34	260,487	D
COMMON STOCK								30,000	I	Held by Timothy E Bixby Family Trust(2)

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

Explanation of Responses:

1. The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.

2. The Reporting Person is Co-Trustee of Timothy E. Bixby Family Trust ("Trust") and has voting and dispositive control over the shares held by Trust.

Remarks:

	/s/ Timothy Bixby	09/05/2025
	** 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 E. Bixby report on Form 4 for LMND?

He reported a sale of 2,906 shares of Lemonade common stock on 09/03/2025 at $50.34 per share.

Why were the 2,906 shares sold according to the filing?

The filing states the sale was not discretionary and was executed to cover tax withholding obligations from the vesting and settlement of restricted stock units.

How many Lemonade shares does Timothy E. Bixby beneficially own after the reported transaction?

After the sale he beneficially owned 260,487 shares directly and 30,000 shares indirectly through the Timothy E Bixby Family Trust.

What is the reporting person's role at Lemonade, Inc. (LMND)?

The reporting person is listed as a Director and Officer with the title Chief Financial Officer.

Does the filing disclose control over the trust-held shares?

Yes, the filing states the reporting person is Co-Trustee of the Timothy E Bixby Family Trust and has voting and dispositive control over the 30,000 trust shares.