Form 4: Lemonade Chief Business Officer Sells Shares to Cover Tax Obligations

Lemonade, Inc.'s Chief Business Officer, Maya Prosor, reported the sale of 252 shares of common stock at $35.25 per share to satisfy tax withholding obligations related to Restricted Stock Unit vesting.

Summary

• Maya Prosor, Chief Business Officer of Lemonade, Inc. (LMND), reported a transaction on June 3, 2025.
• The transaction involved the sale of 252 shares of Lemonade common stock at a price of $35.25 per share.
• This sale was explicitly stated as a non-discretionary transaction to cover tax withholding obligations associated with the vesting and settlement of Restricted Stock Units.
• Following this transaction, Ms. Prosor directly beneficially owns 8,107 shares of common stock.
• Additionally, Ms. Prosor indirectly beneficially owns 29,286 shares through Cohen Holdings, LLC, where she maintains voting and dispositive control.

Sentiment

Score: 7

Explanation: The sentiment is neutral to slightly positive. While it's a sale of shares, the explicit reason (tax withholding on RSU vesting) indicates it's a routine, non-discretionary event rather than a signal of lack of confidence. The insider retains significant ownership.

Positives

• The sale of shares was a non-discretionary transaction, specifically to cover tax withholding obligations, indicating it was not a reflection of a negative outlook on the company by the insider.
• The Chief Business Officer retains significant direct and indirect beneficial ownership in the company (8,107 direct shares and 29,286 indirect shares), demonstrating continued alignment with shareholder interests.

Negatives

• No specific negative aspects are indicated by this routine tax-related transaction.

Risks

• No new risks are introduced or highlighted by this specific Form 4 filing.

Future Outlook

This Form 4 filing does not contain any forward-looking statements or guidance regarding the company's future outlook.

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.
• The Reporting Person is the owner of Cohen Holdings, LLC and has voting and dispositive control over the shares held by Cohen Holdings, LLC.

Industry Context

This Form 4 filing details a routine insider transaction for tax purposes and does not provide broader industry context or trends for the insurance technology sector.

Comparison to Industry Standards

• This document reports a standard insider transaction for tax purposes, which is a common occurrence across all industries when Restricted Stock Units (RSUs) vest.
• It does not provide company-specific performance metrics that would allow for a direct comparison to industry benchmarks or competitors like Root, Inc. (ROOT) or Metromile (now part of Lemonade).

Related Party Transactions

• Maya Prosor indirectly holds 29,286 shares through Cohen Holdings, LLC, an entity she owns and over which she has voting and dispositive control. This is a disclosed related party holding.

Stakeholder Impact

• Shareholders: Minimal direct impact as the sale is a routine tax-related transaction and the insider retains substantial ownership, suggesting continued alignment of interests.
• Employees, Customers, Suppliers, Creditors: No direct impact from this specific insider transaction.

Next Steps

• This Form 4 filing does not outline any specific future actions, events, or milestones for the company.

Key Dates

Keywords

Lemonade Inc., LMND, Form 4, Insider Trading, Stock Sale, Restricted Stock Units, Tax Withholding, Beneficial Ownership, Maya Prosor, Chief Business Officer