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

Lemonade CFO sells 1,893 shares for taxes

Lemonade’s CFO reported a non-discretionary sale of shares to cover tax withholding tied to RSU vesting, leaving him with over 170,000 directly held shares.

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

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) reported that its Chief Financial Officer, Timothy E. Bixby, had 1,893 shares of common stock sold on September 3, 2026 at $54.63 per share. According to the company’s disclosure, this sale was not a discretionary trade but shares withheld and sold to cover tax obligations arising from the vesting and settlement of restricted stock units. After this transaction, Bixby’s direct holdings were 172,370 shares of Lemonade common stock.

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Insider BIXBY TIMOTHY E
Role Chief Financial Officer
Sold 1,893 shs ($103K)
Type Security Shares Price Value
Sale COMMON STOCK F1 1,893 $54.63 $103K
Holdings After Transaction: COMMON STOCK — 172,370 shares (Direct)
Footnotes (1)
  1. F1. The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.
Shares sold 1,893 shares Common stock sold on September 3, 2026 to cover tax withholding
Sale price per share $54.63 per share Price for the 1,893 LMND shares sold on September 3, 2026
Shares held after transaction 172,370 shares CFO’s direct holdings of Lemonade common stock after the sale
Restricted Stock Units financial
"in connection with the vesting and settlement of Restricted Stock Units"
Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.
tax withholding obligations financial
"represents shares sold to cover tax withholding obligations"
non-derivative financial
"transaction_type is listed as non-derivative for the common stock"
open market or private transaction financial
"Sale in open market or private transaction"

FAQ

What insider transaction did Lemonade (LMND) disclose for its CFO?
Lemonade disclosed that CFO Timothy E. Bixby had 1,893 shares of common stock sold on September 3, 2026 at $54.63 per share. The shares were sold to cover tax withholding obligations from vesting restricted stock units.

Was the LMND CFO’s September 3, 2026 stock sale a discretionary trade?
No. The company reports the sale was not a discretionary transaction by the CFO. It represents shares sold solely to cover tax withholding obligations related to the vesting and settlement of restricted stock units.

How many LMND shares does the CFO hold after this reported transaction?
After the September 3, 2026 tax-withholding-related sale, CFO Timothy E. Bixby directly holds 172,370 shares of Lemonade common stock, as stated in the company’s disclosure.

At what price were the LMND shares sold in the CFO’s Form 4 filing?
The reported transaction shows 1,893 shares of Lemonade common stock sold at a price of $54.63 per share on September 3, 2026, in connection with tax withholding on RSU vesting.

Was the LMND CFO’s September 2026 sale under a Rule 10b5-1 trading plan?
The filing indicates the Rule 10b5-1 checkbox is not marked, and the footnote explains the sale covered tax withholding obligations from RSU vesting, rather than being a discretionary or plan-based sale.

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Form 4 Insider Transactions: What Each Field Means →
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SEC Form 4
FORM 4UNITED 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*
BIXBY TIMOTHY E
(Last)(First)(Middle)
C/O LEMONADE, INC.
5 CROSBY STREET, 3RD FLOOR
(Street)
NEW YORK NEW YORK 10013
(City)(State)(Zip)
UNITED STATES
(Country)		2. Issuer Name and Ticker or Trading Symbol
Lemonade, Inc. [ LMND ] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
Director10% Owner
XOfficer (give title below)Other (specify below)
Chief Financial Officer
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
09/03/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

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)
CodeVAmount(A) or (D)Price
COMMON STOCK09/03/2026S(1)1,893D$54.63172,370D
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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Explanation of Responses:
1. The reported sale was not a discretionary transaction by the Reporting Person, and represents shares sold to cover tax withholding obligations in connection with the vesting and settlement of Restricted Stock Units.
Remarks:
/s/ Timothy Bixby09/08/2026
** Signature of Reporting PersonDate
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.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

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