Lemonade (LMND) Insider Activity: CFO Trades 11k Shares Under 10b5-1 Plan

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) – Form 4 filed 02-Jul-2025

Chief Financial Officer Timothy E. Bixby reported two same-day transactions dated 30-Jun-2025:

• Option exercise (Code “M”): 11,000 stock options exercised at an exercise price of $23.69.
• Open-market sale (Code “S”): the 11,000 resulting shares were sold at an average price of $42.69 under a Rule 10b5-1 plan adopted 12-Dec-2024.

After the transactions, Bixby’s direct ownership declined from 274,393 to 263,393 shares. He also holds 30,000 shares indirectly through the Timothy E. Bixby Family Trust, over which he has full voting and dispositive control. In addition, he retains 300,300 stock options outstanding after the exercise.

The option exercised was already fully vested and carries a 09-25-2029 expiration date. No other executives were included in this filing, and no operational or financial performance metrics were disclosed.

While insider sales can signal several motives (liquidity, diversification, tax), the modest size relative to Bixby’s remaining stake and the pre-arranged 10b5-1 plan suggest limited informational value for long-term shareholders.

Positive

• CFO retains a significant equity stake of 263,393 direct shares and 30,000 indirect shares, maintaining alignment with shareholders.
• Transaction executed under a Rule 10b5-1 plan, enhancing transparency and reducing the risk of opportunistic trading.
• Option exercise price of $23.69 vs sale at $42.69 indicates realized value well above strike, reflecting earlier option pricing assumptions.

Negative

• Insider selling by CFO: 11,000 shares sold, which can be perceived negatively despite plan-based nature.
• Direct share count decreased, slightly reducing insider ownership concentration.

Insights

Securities Analyst

TL;DR: CFO sold 11k shares after option exercise; size modest, done under 10b5-1—impact neutral.

Insider sale volume represents roughly 4% of Bixby’s direct holdings, a relatively small proportion that leaves him with over 263k shares plus 30k held via trust. Because the sale was executed under a pre-planned 10b5-1 arrangement, it reduces the likelihood of informational timing. The spread between the $23.69 exercise price and the $42.69 sale price locks in a ~$209k gross gain, but that does not alter Lemonade’s fundamentals. Investors typically view recurring, large insider disposals as bearish; however, isolated, plan-based trades of this scale are generally considered neutral. The retention of more than a quarter-million shares aligns management incentives with shareholders, mitigating governance concerns. Overall, I see no material shift in valuation outlook stemming from this filing.

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)
06/30/2025

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	06/30/2025		M		11,000	A	$23.69	274,393	D
COMMON STOCK	06/30/2025		S(1)		11,000	D	$42.69	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	06/30/2025		M			11,000	(3)	09/25/2029	COMMON STOCK	11,000	$23.69	300,300	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	07/02/2025
	** 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

What did Lemonade (LMND) disclose in the July 2, 2025 Form 4?

The filing shows CFO Timothy E. Bixby exercised 11,000 options at $23.69 and sold the same 11,000 shares at $42.69 on June 30, 2025.

How many LMND shares does the CFO still own after the transaction?

Bixby holds 263,393 shares directly and 30,000 shares indirectly via the Timothy E. Bixby Family Trust.

Was the insider sale conducted under a Rule 10b5-1 plan?

Yes, the sale was made pursuant to a 10b5-1 trading plan adopted on December 12, 2024.

What was the exercise price and sale price of the LMND shares?

The options were exercised at $23.69 per share and the resulting shares were sold at $42.69 per share.

How many stock options does the CFO still hold?

After the transaction, Bixby retains 300,300 stock options with an expiration date of September 25, 2029.