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  4. [Form 4] Lemonade, Inc. Insider Trading Activity

Lemonade Executive Cashes In Options for Major Profit as Stock Climbs

Filing Impact
(Very High)
Filing Sentiment
(Positive)
Form Type
4

Rhea-AI Filing Summary

Lemonade CFO Timothy E. Bixby reported significant insider trading activity on June 23, 2025. The transaction involved two key parts:

  • Exercised 11,000 stock options at $23.69 per share through conversion (Transaction Code: M)
  • Subsequently sold 11,000 shares at $43.36 per share under a pre-established Rule 10b5-1 trading plan from December 2024

Following these transactions, Bixby's holdings include:

  • Direct ownership: 263,393 common shares and 311,300 stock options
  • Indirect ownership: 30,000 shares held in the Timothy E. Bixby Family Trust

The exercised options were fully vested with an expiration date of September 25, 2029. This transaction resulted in a gross profit of approximately $216,370 (difference between sale price and option exercise price).

Positive

  • None.

Negative

  • None.
Insider BIXBY TIMOTHY E
Role Chief Financial Officer
Sold 11,000 shs ($477K)
Approx. gross sale proceeds $477K
Approx. exercise cost $261K
Approx. pre-tax spread $216K
Type Security Shares Price Value
Exercise STOCK OPTION 11,000 $23.69 $261K
Exercise COMMON STOCK 11,000 $23.69 $261K
Sale COMMON STOCK 11,000 $43.36 $477K
holding COMMON STOCK -- -- --
Holdings After Transaction: STOCK OPTION — 311,300 shares (Direct); COMMON STOCK — 263,393 shares (Direct); COMMON STOCK — 30,000 shares (Indirect, Held by Timothy E Bixby Family Trust)
Footnotes (3)
  1. F1. Represents sale pursuant to a Rule 10b5-1 trading plan adopted December 12, 2024.
  2. F2. 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. F3. The stock option is fully vested.

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FAQ

How many LMND shares did CFO Timothy Bixby sell on June 23, 2025?
CFO Timothy Bixby sold 11,000 shares of LMND common stock at a price of $43.36 per share on June 23, 2025. This sale was executed pursuant to a Rule 10b5-1 trading plan adopted on December 12, 2024.

What was the exercise price of LMND stock options exercised by Timothy Bixby?
Timothy Bixby exercised stock options with a conversion price of $23.69 per share. He exercised 11,000 shares of these options which were fully vested and had an expiration date of September 25, 2029.

How many LMND shares does Timothy Bixby own after the June 2025 transactions?
After the reported transactions, Timothy Bixby directly owns 263,393 shares of LMND common stock, plus an additional 30,000 shares held indirectly through the Timothy E Bixby Family Trust. He also holds 311,300 stock options following the transaction.

Was LMND CFO Bixby's stock sale part of a pre-planned trading program?
Yes, Timothy Bixby's sale of 11,000 LMND shares was executed pursuant to a Rule 10b5-1 trading plan that was previously adopted on December 12, 2024. This type of plan allows insiders to pre-schedule trades to avoid accusations of trading on material non-public information.

What is the total profit from LMND CFO Bixby's June 2025 stock transaction?
Timothy Bixby realized a profit of $19.67 per share ($43.36 sale price - $23.69 exercise price) on the 11,000 shares, resulting in a total profit of approximately $216,370 before taxes and fees from the exercise-and-sell transaction.
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)
06/23/2025
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 06/23/2025 M 11,000 A $23.69 274,393 D
COMMON STOCK 06/23/2025 S(1) 11,000 D $43.36 263,393 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 06/23/2025 M 11,000 (3) 09/25/2029 COMMON STOCK 11,000 $23.69 311,300 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 06/25/2025
** 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.

Source: View Original Filing on SEC EDGAR