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LMND Insider: Option Exercise at $11.61 and 38,155-Share Sale Under 10b5-1

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

Rhea-AI Filing Summary

John Peters, Chief Insurance Officer at Lemonade, Inc. (LMND), reported multiple transactions affecting his beneficial ownership. The filing shows a charitable donation of 1,000 common shares on 08/12/2025 with no value received. On 08/13/2025 he acquired 38,155 common shares by exercising a fully vested stock option at an exercise price of $11.61 per share. The same day he sold 38,155 common shares pursuant to a Rule 10b5-1 trading plan at a sale price of $60.00 per share. Following these transactions his reported beneficial ownership is 105,115 shares.

Positive

  • Fully vested option exercise disclosed for 38,155 shares at an $11.61 exercise price, providing clear reporting of option status
  • Sale executed under a Rule 10b5-1 plan, indicating the sale was prearranged and compliant with trading-plan safeguards
  • Charitable donation disclosed of 1,000 shares with no value received, reflecting transparent reporting of gifts

Negative

  • Substantial sale of 38,155 shares at $60.00 reduced the reporting person\'s holdings to 105,115 shares
  • No commentary provided on intent or impact of the sale beyond the 10b5-1 designation, limiting interpretability for investors

Insights

TL;DR Insider exercised vested options, sold the same number of shares under a 10b5-1 plan, and made a small charitable donation.

The filing documents routine insider activity: a fully vested option exercise for 38,155 shares at $11.61 and an immediate sale of 38,155 shares at $60.00 under a Rule 10b5-1 plan on 08/13/2025. The exercise increased gross share holdings briefly but the concurrent sale left the reporting person with 105,115 shares beneficially owned. A separate donation of 1,000 shares on 08/12/2025 is disclosed with no value received. These are transaction-level disclosures without forward-looking commentary or changes to their role.

TL;DR Disclosed actions align with standard insider reporting: vested option exercise, planned sale, and charitable gift.

The Form 4 indicates compliance with disclosure rules: the option was noted as fully vested, the sale was executed pursuant to a Rule 10b5-1 trading plan, and a gift of 1,000 shares is explicitly labeled charitable. The record is signed by an attorney-in-fact and includes transaction codes and prices, providing clear auditability. There are no disclosures of additional derivative holdings beyond the exercised option converting to 38,155 common shares.

Insider Peters John Sheldon
Role Chief Insurance Officer
Sold 38,155 shs ($2.29M)
Type Security Shares Price Value
Exercise STOCK OPTION 38,155 $11.61 $443K
Exercise COMMON STOCK 38,155 $11.61 $443K
Sale COMMON STOCK 38,155 $60.00 $2.29M
Gift COMMON STOCK 1,000 $0.00 --
Holdings After Transaction: STOCK OPTION — 11,845 shares (Direct); COMMON STOCK — 143,270 shares (Direct)
Footnotes (1)
  1. This transaction represents a charitable donation to a third party. No value was received for the gifted shares. Represents sale pursuant to a Rule 10b5-1 trading plan. The stock option is fully vested.
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*
Peters John Sheldon
(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 Insurance Officer
3. Date of Earliest Transaction (Month/Day/Year)
08/13/2025
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 08/12/2025 G(1) V 1,000 D $0 105,115 D
COMMON STOCK 08/13/2025 M 38,155 A $11.61 143,270 D
COMMON STOCK 08/13/2025 S(2) 38,155 D $60 105,115 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
STOCK OPTION $11.61 08/13/2025 M 38,155 (3) 02/05/2029 COMMON STOCK 38,155 $11.61 11,845 D
Explanation of Responses:
1. This transaction represents a charitable donation to a third party. No value was received for the gifted shares.
2. Represents sale pursuant to a Rule 10b5-1 trading plan.
3. The stock option is fully vested.
Remarks:
/s/ Timothy Bixby, Attorney-in-Fact for John Peters 08/15/2025
** 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

FAQ

What transactions did John Peters (LMND) report on the Form 4?

He donated 1,000 shares on 08/12/2025, exercised a fully vested option for 38,155 shares at $11.61 on 08/13/2025, and sold 38,155 shares at $60.00 on 08/13/2025.

How many shares does John Peters beneficially own after these transactions?

105,115 shares beneficially owned following the reported transactions.

Was the sale of shares by John Peters part of a prearranged trading plan?

Yes, the sale of 38,155 shares on 08/13/2025 is reported as executed pursuant to a Rule 10b5-1 trading plan.

What was the exercise price and sale price reported?

Exercise price: $11.61 per share; Sale price: $60.00 per share.

Is there any indication the stock option was vested?

Yes, the filer states the stock option is fully vested.