Peters John Sheldon

Chief Insurance Officer Peters sells 22,728 shares for $1,655,739.60 across 2 transactions; stock up 40% in 30 days but down 22.2% of his holdings

Peters John Sheldon, Chief Insurance Officer at Lemonade, filed 2 separate sales totaling 22,728 shares (22.7K shares) for $1,655,739.60 ($1.7M), reducing his holdings from 102,397 to 79,669 shares (-22.2% of pre-transaction holdings). The blended average sale price of $72.85 reflects transactions on 2025-11-20 and 2025-11-24. Despite the stock's strong 30-day performance of +40.0%, Peters' recent transaction prices ($72.77 and $73.25) represent sales near the 52-week high of $79.14 (stock currently at $73.00, -7.8% from peak). His cross-ticker track record shows a 90-day well-timed rate of 66.67% with an average 90-day return of -0.0% after prior sales, while his LMND-specific prior three trades show mixed timing (2 of 3 well-timed at the 90-day mark but one trade delivered +31.9% 90-day return). The company remains unprofitable despite strong quarterly revenue of $194,500,000 and 22.5% annual growth, which contextualizes the tension between recent price strength and fundamental losses.

Chief Insurance Officer sells 38,155 shares (38.2K) of LMND at $60.00 for $2.3M; stock -3.9% from 52-week high

Peters John Sheldon sold 38,155 shares at $60.00, reducing his holdings by 26.6% from 143,270 to 105,115 shares. The sale occurred at a price near the 52-week high of $59.70, with LMND having rallied +43.7% over 30 days and +76.1% over 90 days. His cross-ticker track record shows a 100.00% well-timed rate on 2 prior sells with average 90-day returns of -16.0%, and his prior trades at LMND (2 sells on 2024-12-30) also delivered -16.0% 90-day declines. Against this backdrop of strong recent price momentum and historically well-timed equity exits, the timing of a substantial reduction in a senior officer's holdings warrants attention. Concurrently, Lemonade posted revenue of $164.1M (latest quarter) with continued losses of $-43.9M and a market cap of $4.2B, indicating the company remains unprofitable despite 22.5% annual growth.

Chief Insurance Officer Peters sold 28,985 shares for $1,120,849.95 via 10b5-1 plan

John Sheldon Peters, Chief Insurance Officer at Lemonade, executed 2 separate sales totaling 28,985 shares for $1,120,849.95 on 2024-12-30, reducing his holdings by 24.5% from 118,493 shares to 89,508 shares. This transaction is part of a pre-arranged 10b5-1 trading plan, meaning it was scheduled in advance rather than a discretionary decision made in response to current market conditions. The sale was executed at a blended average price of $38.67 per share across both transactions. As a scheduled plan execution, this sale reflects pre-planned portfolio adjustments rather than a real-time judgment about company prospects.