Form 4: Lemonade CFO Sells Shares for Tax Obligations

Lemonade's Chief Financial Officer, Timothy E. Bixby, sold 2,906 shares of common stock at $50.34 per share to cover tax withholding obligations related to Restricted Stock Unit vesting.

Summary

• Timothy E. Bixby, Chief Financial Officer of Lemonade, Inc. (LMND), reported the sale of 2,906 shares of common stock.
• The transaction occurred on September 3, 2025, with shares sold at a price of $50.34 each.
• The sale was explicitly stated as a non-discretionary transaction, executed solely to cover tax withholding obligations associated with the vesting and settlement of Restricted Stock Units.
• Following this transaction, Mr. Bixby directly beneficially owns 260,487 shares of common stock.
• Additionally, Mr. Bixby indirectly beneficially owns 30,000 shares held by the Timothy E. Bixby Family Trust, for which he is a Co-Trustee with voting and dispositive control.

Sentiment

Score: 6

Explanation: The transaction is a routine, non-discretionary sale to cover tax obligations related to RSU vesting, which is a common practice for executives and does not indicate a change in management's confidence in the company. This suggests a neutral to slightly positive sentiment as it's not a voluntary divestment.

Positives

• The sale was non-discretionary, specifically to cover tax withholding obligations from RSU vesting, indicating it was not a voluntary divestment based on market outlook or a lack of confidence.

Negatives

• No discretionary negatives identified; the sale was for tax purposes, which is a routine event for executives.

Future Outlook

NA

Management Comments

• "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."

Industry Context

NA

Related Party Transactions

• Timothy E. Bixby is Co-Trustee of the Timothy E. Bixby Family Trust, which holds 30,000 shares indirectly beneficially owned by Mr. Bixby. This is a disclosure of beneficial ownership, not a transaction with a related party.

Stakeholder Impact

• Shareholders: The sale of 2,906 shares represents a minimal dilution, and its non-discretionary nature mitigates concerns about management's confidence in the company's future prospects.
• Employees: No direct impact on employees is indicated by this filing.

Key Dates

Recommendation

The reported sale by the CFO is a non-discretionary transaction to cover tax withholding obligations from RSU vesting, a common and expected event for executives. It does not reflect a change in the company's fundamentals or management's confidence, thus warranting no change to an existing 'hold' position.

Keywords

Lemonade, LMND, Timothy Bixby, CFO, stock sale, Form 4, insider transaction, RSU, tax withholding