Lemonade (NYSE: LMND) CFO disposes 2,227 shares to cover RSU tax withholding

Rhea-AI Filing Summary

Lemonade, Inc. Chief Financial Officer Timothy E. Bixby reported a non-discretionary disposition of 2,227 shares of common stock on June 3, 2026 at $53.17 per share. According to the footnote, these shares were sold solely to cover tax withholding obligations tied to the vesting and settlement of Restricted Stock Units, rather than as a voluntary portfolio decision. After this transaction, Bixby directly holds 247,263 shares of Lemonade common stock.

Insider Trade Summary

Net Seller: 2,227 shares ($118,410)

Net Sell 1 txn

Insider BIXBY TIMOTHY E

Role Chief Financial Officer

Sold 2,227 shs ($118K)

Type	Security	Shares	Price	Value
Sale	COMMON STOCK	2,227	$53.17	$118K

Holdings After Transaction: COMMON STOCK — 247,263 shares (Direct, null)

Footnotes (1)

1. [object Object]

Key Figures

Shares disposed: 2,227 shares Sale price: $53.17 per share Shares held after: 247,263 shares +1 more

4 metrics

Shares disposed 2,227 shares Non-discretionary sale on June 3, 2026

Sale price $53.17 per share Price for 2,227 shares sold

Shares held after 247,263 shares Direct holdings following transaction

Net shares sold 2,227 shares Net-sell direction in summary data

Key Terms

Restricted Stock Units, tax withholding obligations, open-market sale, Form 4

4 terms

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.

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.

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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).

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 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 Financial 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)		2,227	D	$53.17	247,263	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.

Remarks:

	/s/ Timothy Bixby	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)

FAQ

What insider transaction did Lemonade (LMND) report for its CFO?

Lemonade reported that CFO Timothy E. Bixby disposed of 2,227 shares of common stock. The shares were sold on June 3, 2026 to satisfy tax withholding obligations arising from Restricted Stock Unit vesting, rather than as a discretionary open-market sale.

At what price did Lemonade (LMND) shares sell in the CFO’s June 2026 transaction?

The reported shares sold at an average price of $53.17 per share. This price applies to the 2,227 Lemonade common shares disposed of to cover tax withholding obligations associated with the vesting and settlement of Restricted Stock Units held by the CFO.

How many Lemonade (LMND) shares does the CFO hold after this Form 4 filing?

Following the reported transaction, CFO Timothy E. Bixby directly holds 247,263 shares of Lemonade common stock. This post-transaction balance reflects his remaining equity stake after 2,227 shares were sold to cover tax withholding on Restricted Stock Unit vesting.

Was the Lemonade (LMND) CFO’s June 2026 share sale a discretionary trade?

No, the filing footnote states the sale was not a discretionary transaction by the CFO. The 2,227 shares were sold specifically to cover tax withholding obligations connected to the vesting and settlement of Restricted Stock Units granted as equity compensation.

What does the Form 4 footnote say about the Lemonade (LMND) CFO transaction?

The footnote explains the reported sale represents shares sold to cover tax withholding obligations from Restricted Stock Unit vesting and settlement. It clarifies the transaction was not discretionary by the reporting person, framing it as a mechanical tax-related disposition rather than an elective sale.