Form 4: Lemonade Officer Sells 9,000 Shares Under 10b5-1 Plan

Lemonade's Chief Insurance Officer, John Sheldon Peters, sold 9,000 shares of common stock for $90 per share, reducing his direct beneficial ownership to 70,228 shares.

Summary

• John Sheldon Peters, the Chief Insurance Officer of Lemonade, Inc. (LMND), reported a sale of common stock.
• The transaction involved the disposition of 9,000 shares of common stock.
• The shares were sold at a price of $90 per share.
• The sale was executed on January 22, 2026.
• Following this transaction, John Sheldon Peters directly beneficially owns 70,228 shares of Lemonade common stock.
• The sale was conducted pursuant to a Rule 10b5-1 trading plan, which was adopted on August 22, 2025.

Sentiment

Score: 5

Explanation: The sentiment is neutral as this is a routine insider transaction executed under a pre-planned 10b5-1 trading plan, which typically minimizes the signaling effect of such sales.

Future Outlook

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

Industry Context

Insider transactions, particularly those executed under pre-arranged 10b5-1 plans, are a routine part of executive compensation and personal financial management within the insurance technology (insurtech) sector, as in other industries. Such sales do not inherently indicate a change in company fundamentals or management's confidence, especially when part of a pre-scheduled plan.

Stakeholder Impact

• Shareholders: May observe a minor impact on sentiment due to an insider sale, though the pre-planned nature (10b5-1) often mitigates concerns about management's view of future prospects.

Key Dates

Recommendation

The sale of 9,000 shares by Lemonade's Chief Insurance Officer, John Sheldon Peters, is a routine insider transaction executed under a Rule 10b5-1 trading plan adopted several months prior. Such pre-scheduled sales are common for executives for personal financial planning and do not typically signal a change in the company's fundamental outlook or management's confidence. While insider sales can sometimes be viewed negatively, the planned nature of this transaction suggests it is not a reaction to new, adverse information. Therefore, based solely on this Form 4, a 'hold' recommendation is appropriate, as it does not provide new information warranting a change in investment thesis.

Keywords

Lemonade Inc, LMND, Insider Sale, Form 4, John Sheldon Peters, Chief Insurance Officer, 10b5-1 plan