Lemonade (NYSE: LMND) Chief Insurance Officer sells 5,344 shares in tax and 10b5-1 plan

Rhea-AI Filing Summary

Lemonade, Inc. Chief Insurance Officer John Sheldon Peters reported selling a total of 5,344 shares of common stock in open‑market transactions. He sold 1,773 shares on March 3, 2026 at $50.12 per share and 3,571 shares on March 4, 2026 at $52.50 per share.

After these transactions, he directly owned 80,300 shares following the March 3 sale and 76,729 shares following the March 4 sale. A footnote explains that part of the reported selling was not discretionary and represented shares sold to cover tax withholding obligations tied to vesting and settlement of restricted stock units, and another footnote states that a sale was made under a Rule 10b5‑1 trading plan.

Insider Trade Summary

Net Seller: 5,344 shares ($276,340)

Net Sell 2 txns

Insider Peters John Sheldon

Role Chief Insurance Officer

Sold 5,344 shs ($276K)

Type	Security	Shares	Price	Value
Sale	COMMON STOCK	3,571	$52.50	$187K
Sale	COMMON STOCK	1,773	$50.12	$89K

Holdings After Transaction: COMMON STOCK — 76,729 shares (Direct)

Footnotes (1)

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. Represents sale pursuant to a Rule 10b5-1 trading plan.

Form 4 Insider Transactions: What Each Field Means →

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
Estimated average burden
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).

X

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^*

Peters John Sheldon

(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 Insurance Officer

3. Date of Earliest Transaction (Month/Day/Year)
03/03/2026

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	03/03/2026		S(1)		1,773	D	$50.12	80,300	D
COMMON STOCK	03/04/2026		S(2)		3,571	D	$52.5	76,729	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 (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. Represents sale pursuant to a Rule 10b5-1 trading plan.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for John Peters	03/05/2026
	** 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 insider activity did LMND’s Chief Insurance Officer report on this Form 4?

The Form 4 shows Chief Insurance Officer John Sheldon Peters sold 5,344 shares of Lemonade, Inc. common stock in open‑market transactions over two days. These sales are reported as non‑derivative transactions in the company’s common stock.

How many LMND shares did John Sheldon Peters sell and at what prices?

John Sheldon Peters reported selling 1,773 shares of Lemonade, Inc. common stock at $50.12 per share on March 3, 2026, and 3,571 shares at $52.50 per share on March 4, 2026, for a combined total of 5,344 shares sold.

How many LMND shares does John Sheldon Peters hold after these transactions?

After the March 3, 2026 sale, John Sheldon Peters directly held 80,300 Lemonade, Inc. shares, and after the March 4, 2026 sale, he directly held 76,729 shares, as reported in the Form 4 ownership fields.

Were the LMND insider sales discretionary or related to tax obligations?

A footnote explains that one reported sale was not discretionary and involved shares sold to cover tax withholding obligations from vesting and settlement of restricted stock units, indicating part of the activity was driven by tax requirements rather than voluntary trading.

Did any of the LMND insider sales occur under a Rule 10b5-1 plan?

Yes. A separate footnote states that one of the reported sales was executed pursuant to a Rule 10b5‑1 trading plan, which is a pre‑arranged trading program designed to allow insiders to sell shares according to predetermined instructions.

What role does John Sheldon Peters hold at Lemonade, Inc. in this Form 4?

In this Form 4, John Sheldon Peters is identified as an officer of Lemonade, Inc., serving as the company’s Chief Insurance Officer, and the reported common stock transactions are in his capacity as a reporting person.