LMND Lemonade, Inc. Insider Trading

CFO Timothy E Bixby sold 73.0K LMND shares at $79.18 under pre-arranged 10b5-1 plan; stock now $71.02

Timothy E Bixby, who was CFO at the time of filing, sold 73,000 shares of Lemonade at $79.18 on 2026-07-07 as part of a pre-arranged 10b5-1 trading plan adopted on 2026-03-13. The transaction was scheduled, not discretionary. Post-transaction holdings total 174,263 shares, representing a -29.5% reduction versus pre-transaction holdings of 247,263 shares. The company is unprofitable with net income of $-35,800,000.00 against revenue of $258,000,000.00, though annual revenue growth stands at +40.2%. The stock has fallen -28.9% from its 52-week high of $99.90 and currently trades at $71.02, below the sale price of $79.18.

CEO Schreiber sold 9,108 shares of LMND at $99.04 on 2026-01-23; stock now $74.18, down 23.2% from 52-week high.

Schreiber Daniel A., CEO of Lemonade, Inc., sold 9,108 shares at $99.04 on 2026-01-23, reducing his position from 1,523,534 shares to 1,514,426 shares—a modest 0.6% reduction in holdings. The transaction occurred near the upper end of the 52-week range ($25.12–$96.57), before the stock declined 23.2% to its current price of $74.18. The company generated $194.5M in quarterly revenue with 22.5% annual growth but remains unprofitable with a net loss of $37.5M in the most recent quarter. This sale represents the insider's second LMND transaction on consecutive days (following a sale on 2026-01-22), though the prior trade outcome remains unmeasurable. The sale occurred at a notably higher price than current levels, and the subsequent price decline warrants attention given the CEO's position; however, the small share reduction relative to his 1.51M remaining position limits the direct portfolio impact and affords limited insight into executive conviction regarding near-term prospects.

CEO Schreiber sold 126,625 shares of LMND at $94.74 on 2026-01-22; retains 1,523,534 shares post-sale amid stock surge (+78.8% in 90 days).

Schreiber sold 126,625 shares for $11,996,452.50, reducing his holdings from 1.65M to 1.52M shares (-7.7% reduction). The sale occurred at $94.74, within 3 percentage points of the 52-week high of $96.57, following a 78.8% rally over 90 days and 16.8% gain in the prior 30 days. The company remains unprofitable with negative $37.5M net income on $194.5M quarterly revenue, despite 22.5% annual growth. This CEO sale at near-peak valuation comes amid rapid share appreciation, though the insider retains substantial equity (1.52M shares), limiting the signal's interpretive strength.

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.

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.

Lemonade CFO Bixby sells entire 30,000 share stake ($2.3M) at $75.51; complete portfolio exit

Timothy Bixby, CFO of Lemonade, liquidated his entire equity position on 2025-11-11, selling 30,000 shares for $2,265,300.00 and reducing his holdings from 30,000 shares to 0 shares (-100.0%). This represents a complete exit, contrasting with his prior three open-market purchases at LMND (on 2024-06-14, 2024-06-13, and 2024-03-06). The sale occurred at $75.51, near the 52-week high of $79.14, after the stock had risen +52.9% over the prior 30 days and +31.6% over 90 days. At the same-ticker level, his two most recent purchases (June 2024) each showed strong 90-day returns of +25.1% and +11.9%, suggesting he had previously entered the stock during favorable periods. The company remains unprofitable (net income $-37.5M against revenue $194.5M), though annual revenue growth is +22.5%. This transition from accumulated holdings to zero position, following a sharp recent run-up, is material context for shareholders evaluating officer liquidity patterns.

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.

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.