Lemonade officer sells 3,108 shares of stock

Lemonade, Inc. (LMND) reported that Chief Insurance Officer John Sheldon Peters disposed of common stock in two transactions.

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) reported that Chief Insurance Officer John Sheldon Peters disposed of common stock in two transactions. On September 3, 2026, 859 shares were sold at $54.63 per share in a non-discretionary transaction to cover tax withholding obligations related to vesting and settlement of Restricted Stock Units. On September 4, 2026, 2,249 shares were sold at $54.45 per share pursuant to a Rule 10b5-1 trading plan, with no post-transaction holdings reported in this filing.

Insider Trade Summary 10b5-1

Net Seller: 3,108 shares

Net Sell 2 txns

Insider Peters John Sheldon

Role Chief Insurance Officer

Sold 3,108 shs ($169K)

Type	Security	Shares	Price	Value
Sale	COMMON STOCK F2	2,249	$54.45	$122K
Sale	COMMON STOCK F1	859	$54.63	$47K

Holdings After Transaction: COMMON STOCK — 73,834 shares (Direct)

Footnotes (2)

1. F1. 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. F2. Represents sale pursuant to a Rule 10b5-1 trading plan.

Key Figures

Shares sold September 3, 2026: 859 shares Price per share September 3, 2026: $54.63 per share Shares sold September 4, 2026: 2,249 shares +2 more

5 metrics

Shares sold September 3, 2026 859 shares Non-discretionary sale to cover tax withholding obligations for RSU vesting

Price per share September 3, 2026 $54.63 per share Sale of 859 Lemonade common shares

Shares sold September 4, 2026 2,249 shares Sale pursuant to a Rule 10b5-1 trading plan

Price per share September 4, 2026 $54.45 per share Sale of 2,249 Lemonade common shares

Total shares sold 3,108 shares Combined total of both reported transactions

Key Terms

Rule 10b5-1 trading plan, Restricted Stock Units, tax withholding obligations

3 terms

Rule 10b5-1 trading plan regulatory

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

A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.

Restricted Stock Units financial

"in connection with the vesting and settlement of Restricted Stock Units"

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

tax withholding obligations financial

"represents shares sold to cover tax withholding obligations in connection with"

FAQ

What insider transactions did LMND report for John Sheldon Peters in this Form 4?

The filing reports that Chief Insurance Officer John Sheldon Peters sold 859 shares of Lemonade common stock on September 3, 2026 and 2,249 shares on September 4, 2026, for a total of 3,108 shares disposed of.

At what prices were the LMND shares sold in the reported transactions?

The 859 shares of Lemonade common stock sold on September 3, 2026 were at $54.63 per share, and the 2,249 shares sold on September 4, 2026 were at $54.45 per share, both described as sales in open market or private transactions.

Were the LMND stock sales by John Sheldon Peters discretionary?

The filing states the September 3, 2026 sale of 859 shares was not a discretionary transaction and represented shares sold to cover tax withholding obligations in connection with RSU vesting and settlement.

Did the LMND Form 4 indicate use of a Rule 10b5-1 trading plan?

Yes. The filing affirms Rule 10b5-1 status and notes the September 4, 2026 sale of 2,249 shares was a sale pursuant to a Rule 10b5-1 trading plan, indicating it was made under a pre-arranged trading arrangement.

What role does John Sheldon Peters hold at LMND in this Form 4?

John Sheldon Peters is identified as an officer of Lemonade, Inc., serving as the company’s Chief Insurance Officer, according to the reporting person information in the Form 4.

Does the LMND Form 4 show Peters’ share holdings after these transactions?

No. For both reported transactions, the field for shares beneficially owned following the transaction is left blank, so this Form 4 does not state his post-transaction holdings.

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Available on EDGAR 09/08/2026 - 05:33 PM Accepted by SEC EDGAR 09/08/2026 - 05:33 PM Learn about SEC filing dates

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 NEW YORK 10013

(City) (State) (Zip)

UNITED STATES

(Country)

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
09/03/2026

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

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

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

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	09/03/2026		S(1)		859	D	$54.63	76,083	D
COMMON STOCK	09/04/2026		S(2)		2,249	D	$54.45	73,834	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	09/08/2026
	** 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.
* Form 4: SEC 1474 (03-26)