[Form 4] Lemonade, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Form 4 Snapshot: On 06/16/2025 Lemonade, Inc. (LMND) Chief Financial Officer Timothy E. Bixby exercised 11,000 fully-vested stock options at an exercise price of $23.69. Immediately thereafter, he sold the same 11,000 common shares in two open-market trades executed under a Rule 10b5-1 plan adopted 12/12/2024.

Transaction detail

• 5,000 shares sold at $41.06
• 6,000 shares sold at $42.50
• Gross sale proceeds ≈ $711,000
• Option exercise cost ≈ $260,590

Because the amount sold matched the option shares acquired, Bixby’s direct share count returned to its pre-transaction level of 263,393. He also retains 30,000 shares held indirectly through the Timothy E. Bixby Family Trust and continues to hold 322,300 outstanding stock options that expire 09/25/2029.

Investor considerations

• The sale was pre-scheduled, limiting negative signalling risk.
• No net change in direct share ownership preserves management-shareholder alignment.
• CFO still controls roughly 293k total shares (direct + trust), indicating a substantial ongoing stake.

Positive

• Sale executed under a Rule 10b5-1 plan, reducing concerns about opportunistic insider trading.
• CFO’s direct holding remains at 263,393 shares, sustaining management-shareholder alignment.

Negative

• Gross insider sale of 11,000 shares may be viewed negatively by some investors despite being offset by option exercise.
• Reduction of 11,000 vested options slightly lowers future upside participation.

Insights

Equity Research Analyst

TL;DR Neutral: pre-planned option exercise offset by equal share sale; CFO’s stake unchanged, limited signalling impact.

The filing shows a standard option-exercise-and-sell pattern. Exercising at $23.69 and selling at ~$41-42 locks in value without altering Bixby’s economic exposure. Because the trades were executed under a December-2024 10b5-1 plan, they do not necessarily reflect current views on valuation. The absence of a net share reduction and the retention of >260k shares means insider alignment remains intact. From a valuation standpoint, this event is informational rather than fundamental and is unlikely to move LMND shares materially.

Corporate Governance Specialist

TL;DR Governance-neutral: compliant 10b5-1 trading, no red flags detected.

Key governance items: 1) timely filing; 2) sales tied to a pre-existing 10b5-1 plan, satisfying new SEC affirmative-defense criteria; 3) option fully vested, eliminating concerns over premature monetisation. The CFO’s unchanged ownership and continuing sizeable option position support ongoing incentive alignment. No compliance or disclosure issues are evident.

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^*

BIXBY TIMOTHY E

(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 Financial Officer

3. Date of Earliest Transaction (Month/Day/Year)
06/16/2025

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	06/16/2025		M		11,000	A	$23.69	274,393	D
COMMON STOCK	06/16/2025		S(1)		5,000	D	$41.06	269,393	D
COMMON STOCK	06/16/2025		S(1)		6,000	D	$42.5	263,393	D
COMMON STOCK								30,000	I	Held by Timothy E Bixby Family Trust(2)

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
STOCK OPTION	$23.69	06/16/2025		M			11,000	(3)	09/25/2029	COMMON STOCK	11,000	$23.69	322,300	D

Explanation of Responses:

1. Represents sale pursuant to a Rule 10b5-1 trading plan adopted December 12, 2024.

2. The Reporting Person is Co-Trustee of Timothy E. Bixby Family Trust ("Trust") and has voting and dispositive control over the shares held by Trust.

3. The stock option is fully vested.

Remarks:

	/s/ Timothy Bixby	06/18/2025
	** 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

How many LMND shares did CFO Timothy Bixby sell on 06/16/2025?

He sold 11,000 shares in two transactions (5,000 + 6,000).

At what prices were the Lemonade shares sold?

Shares were sold at $41.06 and $42.50 per share.

How many LMND shares does the CFO own after the transactions?

Direct ownership stands at 263,393 shares; an additional 30,000 shares are held via family trust.

Was the insider sale executed under a 10b5-1 trading plan?

Yes, the filing cites a plan adopted on 12/12/2024.

What was the exercise price of the options and how many were exercised?

Bixby exercised 11,000 options at an exercise price of $23.69.

How many stock options does the CFO still hold?

He retains 322,300 options expiring on 09/25/2029.