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Lemonade Executive Nets 90% Profit on Stock Option Exercise and Sale

Filing Impact
(Moderate)
Filing Sentiment
(Positive)
Form Type
4

Rhea-AI Filing Summary

Lemonade Chief Operating Officer Adina Eckstein executed a significant insider transaction on June 23, 2025, involving both the exercise of stock options and subsequent sale of shares:

  • Exercised 5,000 stock options at $23.69 per share
  • Immediately sold 5,000 shares at $45.00 per share
  • The sale was conducted under a pre-established Rule 10b5-1 trading plan from December 5, 2024
  • After the transactions, Eckstein holds 189,653 shares directly and 1,250 stock options

The transaction resulted in a gross profit of approximately $106,550 (($45.00 - $23.69) × 5,000 shares). The options were fully vested at the time of exercise, with an original expiration date of September 25, 2029.

Positive

  • None.

Negative

  • None.
Insider Eckstein Adina
Role Chief Operating Officer
Sold 5,000 shs ($225K)
Type Security Shares Price Value
Exercise STOCK OPTION 5,000 $23.69 $118K
Exercise COMMON STOCK 5,000 $23.69 $118K
Sale COMMON STOCK 5,000 $45.00 $225K
Holdings After Transaction: STOCK OPTION — 1,250 shares (Direct); COMMON STOCK — 194,653 shares (Direct)
Footnotes (1)
  1. Represents sale pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024. The stock option is fully vested.
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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).
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*
Eckstein Adina
(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 Operating 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 5,000 A $23.69 194,653 D
COMMON STOCK 06/23/2025 S(1) 5,000 D $45 189,653 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 $23.69 06/23/2025 M 5,000 (2) 09/25/2029 COMMON STOCK 5,000 $23.69 1,250 D
Explanation of Responses:
1. Represents sale pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024.
2. The stock option is fully vested.
Remarks:
/s/ Timothy Bixby, Attorney-in-Fact for Adina Eckstein 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

FAQ

How many LMND shares did COO Adina Eckstein sell on June 23, 2025?

Adina Eckstein sold 5,000 shares of LMND common stock on June 23, 2025 at a price of $45 per share. This transaction was executed pursuant to a Rule 10b5-1 trading plan adopted on December 5, 2024.

What was the exercise price of LMND stock options exercised by Adina Eckstein?

Adina Eckstein exercised stock options with a strike price of $23.69 per share. She exercised 5,000 options that were set to expire on September 25, 2029.

How many LMND shares does Adina Eckstein own after the reported transactions?

Following the reported transactions, Adina Eckstein directly owns 189,653 shares of LMND common stock. She also retains 1,250 stock options that are fully vested.

What is Adina Eckstein's position at LMND and was this a planned sale?

Adina Eckstein serves as the Chief Operating Officer (COO) of Lemonade, Inc. The sale was planned, executed through a Rule 10b5-1 trading plan that was established on December 5, 2024, which indicates this was a pre-scheduled transaction rather than spontaneous selling.