Lemonade (NYSE: LMND) Chief Insurance Officer sells 3,444 shares under 10b5-1 plan

Rhea-AI Filing Summary

Lemonade, Inc. Chief Insurance Officer John Sheldon Peters reported an open-market sale of common stock. On July 6, 2026, he sold 3,444 shares of Lemonade common stock at $79.00 per share. After this transaction, he directly holds 77,942 shares of common stock. The filing notes that this sale was made pursuant to a Rule 10b5-1 trading plan adopted on March 11, 2026, indicating the transaction was pre-scheduled rather than a discretionary trade.

Insider Trade Summary

Net Seller: 3,444 shares ($272,076)

Net Sell 1 txn

Insider Peters John Sheldon

Role Chief Insurance Officer

Sold 3,444 shs ($272K)

Type	Security	Shares	Price	Value
Sale	COMMON STOCK	3,444	$79.00	$272K

Holdings After Transaction: COMMON STOCK — 77,942 shares (Direct, null)

Footnotes (1)

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Key Figures

Shares sold: 3,444 shares Sale price per share: $79.00 per share Shares held after transaction: 77,942 shares +2 more

5 metrics

Shares sold 3,444 shares Open-market sale of common stock on July 6, 2026

Sale price per share $79.00 per share Price for the 3,444 Lemonade common shares sold

Shares held after transaction 77,942 shares Direct ownership by John Sheldon Peters following the sale

Trading plan adoption date March 11, 2026 Adoption date of Rule 10b5-1 plan governing this sale

Transaction date July 6, 2026 Date of reported open-market sale

Key Terms

Rule 10b5-1 trading plan, open-market sale, Form 4, Chief Insurance Officer

4 terms

Rule 10b5-1 trading plan regulatory

"Represents sale pursuant to a Rule 10b5-1 trading plan, adopted on March 11, 2026."

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.

open-market sale financial

"transaction_action: open-market sale, transaction_code_description: Sale in open market or private transaction"

An open-market sale is when a shareholder sells existing shares directly on a public exchange to any willing buyer, rather than through a private deal. Think of it like putting goods on a busy market stall where price is set by supply and demand; for investors it matters because such sales increase available supply, can put short-term downward pressure on the stock price, and signal changes in liquidity or investor confidence.

Form 4 regulatory

"INSIDER FILING DATA (Form 4): {"

Form 4 is a official document that company insiders, such as executives or major shareholders, file with regulators whenever they buy or sell company shares. It provides transparency about how those with inside knowledge are trading, helping investors see if insiders are confident in the company's prospects or may be selling for personal reasons. This information can influence investor decisions by revealing insiders' perspectives on the company's value.

Chief Insurance Officer financial

"officer_title: Chief Insurance Officer"

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Form 4 Insider Transactions: What Each Field Means →

Available on EDGAR 07/08/2026 - 09:41 PM Accepted by SEC EDGAR 07/08/2026 - 09:40 PM Learn about SEC filing dates

FAQ

What insider transaction did Lemonade (LMND) report in this Form 4?

Lemonade reported that Chief Insurance Officer John Sheldon Peters sold 3,444 shares of common stock. The sale was an open-market transaction at $79.00 per share and was executed under a pre-established Rule 10b5-1 trading plan.

How many Lemonade (LMND) shares did the executive sell and at what price?

John Sheldon Peters sold 3,444 shares of Lemonade common stock at a price of $79.00 per share. The transaction was recorded as an open-market sale on July 6, 2026, according to the Form 4 filing.

How many Lemonade (LMND) shares does the insider hold after the reported sale?

Following the reported transaction, John Sheldon Peters holds 77,942 shares of Lemonade common stock directly. This post-transaction balance is disclosed in the Form 4 and reflects his remaining equity position after the 3,444-share sale.

Was the Lemonade (LMND) insider sale made under a Rule 10b5-1 plan?

Yes. The Form 4 states the 3,444-share sale was made pursuant to a Rule 10b5-1 trading plan. The plan was adopted on March 11, 2026, indicating the sale was pre-arranged rather than timed opportunistically.

What role does John Sheldon Peters hold at Lemonade (LMND)?

John Sheldon Peters serves as Lemonade’s Chief Insurance Officer. His role is identified in the Form 4 filing, which reports his open-market sale of 3,444 common shares and his resulting direct ownership of 77,942 shares.

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).

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)
07/06/2026

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	07/06/2026		S		3,444(1)	D	$79	77,942	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. Represents sale pursuant to a Rule 10b5-1 trading plan, adopted on March 11, 2026.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for John Peters	07/08/2026
	** 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)