Eckstein Adina

COO Eckstein Adina sold 7,919 shares of LMND at $84.15 on 2025-12-11 under 10b5-1 plan; 188.4K shares remain.

Eckstein Adina, COO of Lemonade, Inc., executed a scheduled sale of 7,919 shares at $84.15 pursuant to a pre-arranged 10b5-1 trading plan adopted on 2025-09-08. The sale reduced her holdings by approximately 4.0% to 188,391 shares post-transaction. Since this transaction is part of an automated, pre-arranged plan rather than a discretionary trade, it reflects a pre-determined schedule established months prior and does not reflect real-time market assessment or recent management sentiment. The modest reduction in absolute share count and the structured nature of the execution are consistent with a routine equity plan transaction.

COO Eckstein sold 7,919 shares at $81.15 (on 2025-12-10) with 5 prior LMND sales within 3 days; stock up +56.0% over 90 days.

Eckstein Adina, Chief Operating Officer, sold 7,919 shares of Lemonade at $81.15 on 2025-12-10, reducing holdings by 3.9% to 196,310 shares. The transaction follows an unusual cluster of same-ticker selling: five prior sales at LMND occurred on 2025-12-08 and 2025-12-09, with none yet reaching measurable 30-day or 90-day outcome windows. Across his cross-ticker track record, prior sells show a 100.00% well-timed rate (average 90d return -5.4%), indicating historical accuracy in selling before declines. The broader context reveals the company remains unprofitable (net income $-37.5M in the latest quarter) despite +22.5% revenue growth, and LMND stock has already reached its 52-week high of $82.01 as of the current price check. The rapid succession of insider sales over a 3-day window, combined with the stock trading at peak valuation levels and the company's ongoing net losses, warrants scrutiny of whether this represents a deliberate exit or rebalancing activity by the COO.

COO Adina Eckstein sells 70.8K shares ($5.5M) via scheduled 10b5-1 plan; post-sale holding 204.2K shares

Adina Eckstein, Chief Operating Officer of Lemonade, Inc., executed 4 separate sales totaling 70,794 shares for $5,536,946.06 at a blended average price of $78.21 per share on 2025-12-08 and 2025-12-09. This transaction is governed by a pre-arranged 10b5-1 trading plan adopted on 2025-09-08, meaning the sales were scheduled and non-discretionary rather than driven by current market conditions or individual judgment. Eckstein's holdings decreased from 275,023 shares to 204,229 shares, representing a -25.7% reduction in her position. The structured, plan-based nature of these sales limits inferences about the COO's current conviction or near-term outlook for the stock.

COO Eckstein sells 45,988 shares of LMND for $3,387,864 via pre-arranged 10b5-1 plan on Nov 7-10.

Adina Eckstein, Chief Operating Officer, executed 3 separate sales totaling 45,988 shares for $3,387,864.00 at an average price of $73.67 per share across November 7-10, 2025. This sale reduced her holdings from 273,975 shares to 227,987 shares, a reduction of 16.8% of her pre-transaction position. The transaction was conducted under a pre-arranged 10b5-1 trading plan, meaning it was scheduled in advance and not a discretionary trade decision. This filing documents routine capital allocation by a key executive under a planned divestiture schedule.

COO Adina Eckstein sold 47,288 shares for $2,127,960.00 via pre-arranged 10b5-1 plan on Nov 19-21.

Eckstein Adina, Chief Operating Officer of Lemonade, Inc., executed 6 separate sales totaling 47,288 shares for $2,127,960.00 across two trading dates (Nov 19-21, 2024) at prices ranging from $40.00 to $50.00. This represents a reduction of 20.0% from pre-transaction holdings of 236,941 shares, leaving post-transaction holdings of 189,653 shares. The transaction was conducted under a pre-arranged 10b5-1 trading plan adopted on 2024-06-14, meaning the sales were scheduled in advance rather than discretionary. The blended average sale price was $45.00, and no prior trading activity or comparative context is available for this insider at this ticker.