Lemonade executive sells shares for tax withholding

Lemonade, Inc. Chief Insurance Officer John Sheldon Peters reported open-market sales of company common stock that were tied to equity compensation.

Rhea-AI Filing Summary

Lemonade, Inc. Chief Insurance Officer John Sheldon Peters reported open-market sales of company common stock that were tied to equity compensation. He sold 1,735 shares on June 3 at $53.17 per share and 3,608 shares on June 4 at $52.94 per share, totaling 5,343 shares. After these transactions, he directly held 81,386 shares. A footnote explains that part of the activity represents shares sold to cover tax withholding obligations upon vesting of Restricted Stock Units and that sales were made pursuant to a Rule 10b5-1 trading plan, indicating these were pre-arranged, routine transactions rather than discretionary trades based on short-term market views.

Insider Trade Summary 10b5-1

Net Seller: 5,343 shares

Net Sell 2 txns

Insider Peters John Sheldon

Role Chief Insurance Officer

Sold 5,343 shs ($283K)

Type	Security	Shares	Price	Value
Sale	COMMON STOCK	3,608	$52.94	$191K
Sale	COMMON STOCK	1,735	$53.17	$92K

Holdings After Transaction: COMMON STOCK — 81,386 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 June 3: 1,735 shares at $53.17 Shares sold June 4: 3,608 shares at $52.94 Total shares sold: 5,343 shares +2 more

5 metrics

Shares sold June 3 1,735 shares at $53.17 Open-market sale of common stock on June 3

Shares sold June 4 3,608 shares at $52.94 Open-market sale of common stock on June 4

Total shares sold 5,343 shares Combined sales reported in this Form 4

Shares held after transactions 81,386 shares Direct ownership following reported sales

Highest reported sale price $53.17 per share Sale price on June 3 transaction

Key Terms

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

4 terms

Rule 10b5-1 trading plan financial

"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 the vesting"

open-market sale financial

"transaction_action": "open-market sale""

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.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transactions did Lemonade (LMND) disclose in this Form 4?

Lemonade reported share sales by its Chief Insurance Officer. John Sheldon Peters sold 1,735 shares on June 3 and 3,608 shares on June 4, totaling 5,343 common shares, while remaining directly invested in 81,386 shares after these transactions.

At what prices did the Lemonade (LMND) executive sell shares?

The Lemonade executive’s reported sales occurred around $53 per share. He sold 1,735 shares at $53.17 on June 3 and 3,608 shares at $52.94 on June 4, reflecting routine open-market transactions linked to equity compensation.

How many Lemonade (LMND) shares does the insider hold after these sales?

After the reported transactions, the insider holds 81,386 shares. This figure reflects his remaining direct ownership of Lemonade common stock following the sale of a combined 5,343 shares over two trading days.

Were the Lemonade (LMND) insider sales discretionary trades?

The filing states the reported sale was not discretionary. A footnote explains that shares were sold to cover tax withholding obligations tied to Restricted Stock Unit vesting, which makes the transaction more mechanical than an active market-timing decision.

Did Lemonade’s (LMND) insider trade under a Rule 10b5-1 plan?

Yes, the Form 4 notes use of a Rule 10b5-1 trading plan. A footnote specifies that the sale was executed pursuant to such a pre-arranged plan, suggesting the timing was scheduled in advance rather than driven by short-term market developments.

What type of Lemonade (LMND) security was involved in this Form 4?

The transactions involved Lemonade common stock. The Form 4 lists each transaction as non-derivative common stock, separate from the underlying Restricted Stock Units whose vesting triggered associated tax-withholding-related sales.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 06/05/2026 - 05:33 PM EDT 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)
06/03/2026

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	06/03/2026		S(1)		1,735	D	$53.17	84,994	D
COMMON STOCK	06/04/2026		S(2)		3,608	D	$52.94	81,386	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	06/05/2026
	** 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.
* Form 4: SEC 1474 (03-26)