Form 4: Lemonade CBO Sells Shares for Tax Obligations

Lemonade's Chief Business Officer, Maya Prosor, sold 198 shares of common stock at $72.74 per share to cover tax withholding obligations related to vested Restricted Stock Units.

Summary

• Maya Prosor, Chief Business Officer of Lemonade, Inc. (LMND), reported a transaction involving company common stock.
• On December 2, 2025, Prosor sold 198 shares of Lemonade common stock at a price of $72.74 per share.
• The sale was not a discretionary transaction but was executed to cover tax withholding obligations associated with the vesting and settlement of Restricted Stock Units.
• Following the transaction, Prosor directly beneficially owns 7,627 shares of common stock.
• Additionally, Prosor indirectly beneficially owns 29,286 shares through Cohen Holdings, LLC, where she has voting and dispositive control.
• The transaction was made pursuant to a Rule 10b5-1(c) plan.

Sentiment

Score: 5

Explanation: The transaction is a routine, non-discretionary sale to cover tax obligations from RSU vesting, which is a neutral event for company sentiment. It does not reflect a change in management's outlook on the company.

Positives

• The underlying event of Restricted Stock Units (RSUs) vesting indicates a compensation event for the Chief Business Officer, which is a positive for the executive.
• The transaction was non-discretionary, executed to cover tax withholding, suggesting it is not a signal of lack of confidence in the company.

Negatives

• The direct beneficial ownership of common stock by the Chief Business Officer decreased by 198 shares.

Future Outlook

NA

Industry Context

NA

Related Party Transactions

• Maya Prosor indirectly holds 29,286 shares through Cohen Holdings, LLC, where she is the owner and has voting and dispositive control. This clarifies the nature of her indirect beneficial ownership.

Stakeholder Impact

• Shareholders: Minimal impact as the transaction is a routine, non-discretionary sale for tax purposes and does not signal a change in management's confidence.
• Employees: The vesting of RSUs is a standard part of executive compensation, which can be a positive for employee retention and motivation.

Key Dates

Recommendation

This Form 4 reports a routine, non-discretionary sale of shares by a Chief Business Officer solely to cover tax withholding obligations associated with RSU vesting. Such transactions are common and do not typically indicate a change in the insider's view of the company's prospects. Therefore, this filing alone does not provide a basis for a change in investment recommendation; a 'hold' stance is maintained.

Keywords

Lemonade, LMND, Maya Prosor, Chief Business Officer, insider transaction, Form 4, stock sale, RSU vesting, tax withholding, Rule 10b5-1