ROOT Root, Inc. Insider Trading

CEO Timm Alexander sold 6,336 shares of ROOT at $83.00 (Dec 10); stock now -54.4% from 52-week high.

CEO Timm Alexander sold 6,336 shares at $83.00, reducing holdings by 4.0% to 151,412 shares. The sale occurred when ROOT was trading well above its current price of $81.02, which now sits 54.4% below the 52-week high of $177.69. Notably, Alexander's prior five trades at ROOT were all well-timed at the 90-day mark, with negative 90-day returns ranging from -10.8% to -29.4%, suggesting a pattern of selling into weakness or ahead of further declines. His cross-ticker track record shows a 87.50% well-timed selling rate, demonstrating consistent execution relative to subsequent price action. The current valuation backdrop—P/E of 60.46 with recent quarterly net income of -$5.4M—may be relevant context for investor assessment of the company's trajectory and insider positioning.

ROOT President/CTO Bonakdarpour sells 5,750 shares at $89.74; stock down -25.2% in 30 days, -38.1% in 90 days

Mahtiyar Bonakdarpour, President and CTO of Root, Inc., sold 5,750 shares (274.2K shares post-transaction) at $89.74 on 2025-09-02, totaling $516,005.00. The sale occurred while ROOT's stock has declined -25.2% over the past 30 days and -38.1% over 90 days, currently trading at $93.92 or -47.1% from its 52-week high of $177.69. Bonakdarpour's prior trading at ROOT shows a 1-of-5 success rate at the 90-day mark; his most recent ROOT sale on 2025-06-02 saw a 90-day return of -29.4% (well-timed), but his cross-ticker track record on sales reveals a 50.00% well-timed rate with an average 90-day post-sale return of -14.5%. The company's fundamentals show revenue of $382.9M (latest quarter), net income of $22.0M, and annual revenue growth of +158.6%, yet the stock trades at a P/E of 46.73 with a market cap of $4.0B, suggesting valuation compression despite strong growth.

ROOT CEO Timm Alexander sells 10,861 shares across 4 transactions for $965,360.28; stock down 25.2% in 30 days

Timm Alexander, CEO of Root, Inc., executed 4 separate sales on 2025-09-02 totaling 10,861 shares for $965,360.28 at an average price of $88.88, reducing his holdings by 6.4% to 157,748 shares. The timing is noteworthy: the stock has declined 25.2% over the past 30 days and 38.1% over 90 days, placing it 47.1% below its 52-week high. Across his 4 prior sales at ROOT, Alexander's timing was strong, with 3 of 4 preceding sales showing negative 90-day returns (well-timed sells), though the most recent pair in June experienced a 5.3% 30-day decline followed by a 29.4% 90-day decline. The scale of this transaction—nearly $1M in proceeds—and the sharp recent price deterioration against a 158.6% annual revenue growth backdrop raises questions about near-term headwinds or valuation concerns despite strong top-line expansion.

ROOT President and CTO Bonakdarpour sells 5,256 shares ($686.4K) at $130.60; retains 281.6K shares post-sale.

Bonakdarpour sold 5,256 shares (1.8% reduction) on 2025-06-02 at $130.60, realizing $686,433.60 while maintaining a substantial 281,645-share position. His prior sell at ROOT on 2025-04-02 showed a +14.7% 30-day return, indicating the stock rose after that earlier exit. At the same-ticker level, his four prior buys at ROOT all experienced negative 90-day returns (-14.7%, -26.6%, -4.1%, -3.7%), and 0 of his 4 measurable prior ROOT trades were well-timed at the 90-day mark. The stock is currently $133.99, down 24.6% from its 52-week high of $177.69 and down 6.7% over 30 days. ROOT's fundamentals show strong revenue growth (+158.6% year-over-year) and profitability ($18.4M net income on $349.4M quarterly revenue), but the elevated P/E of 102.28 reflects significant premium valuation.

CEO Timm Alexander E. sells 8,290 shares at $130.60 for $1,082,674.00 at ROOT

Chief Executive Officer Timm Alexander E. executed 2 separate sales totaling 8,290 shares for $1,082,674.00 at a blended average price of $130.60 on 2025-06-02, reducing his holdings by 4.7% to 168,609 shares post-transaction. The current price of $133.99 is -24.6% from the 52-week high of $177.69, and the stock has declined 6.7% over the past 30 days, suggesting the sale occurred near a local peak relative to recent performance. His 2 prior same-ticker sales at ROOT (on 2025-04-02 and 2025-04-01) showed positive 30-day returns of +14.7% and +2.0% respectively, indicating prior sales were followed by further gains rather than declines; however, those outcomes remain within the near-term window and lack 90-day measurability. The company fundamentals show accelerating growth with annual revenue growth of +158.6%, net income of $18,400,000.00 on quarterly revenue of $349,400,000.00, though the P/E of 102.28 reflects a richly valued profile. This sale represents a discretionary reduction in a highly profitable stake rather than a full exit, and its significance is moderated by the absence of broader insider selling patterns or material adverse signals in the narrative.

10% owner Malka Meyer sells 225,000 shares for $30.6M; post-trade holdings 503,800 shares; stock +4.7% (30d), +43.0% (90d).

Malka Meyer, a 10% owner at Root, Inc., executed 3 separate sales totaling 225,000 shares for $30,558,066.01 at a blended average price of $135.81 on 2025-04-30, reducing her shareholding by -30.9% to 503,800 shares post-transaction. The filing flags a derivative-conversion transaction (Form 4 Table II not yet populated), so the 503,800 figure represents only the Table I open-market holdings, not her full economic position. Root's fundamentals show strong growth (annual revenue +158.6%) with $305.7M quarterly revenue and $22.8M net income, though valuation remains elevated at 36.37x P/E against a $5.9B market cap. The stock has risen +4.7% in the 30 days since the sale and +43.0% over 90 days, continuing a recovery from a 52-week low of $35.83 toward the recent high of $177.69; the current price of $139.67 is -21.4% from the 52-week peak. Across her same-ticker history at ROOT (5 prior sells on 2024-11-11), none of the insider's prior exits proved well-timed at the 90-day mark—all generated positive subsequent returns—suggesting this sale is also occurring during an upward trajectory rather than ahead of a downturn.

ROOT President/CTO Bonakdarpour sold 5,515 shares at $124.78 on 2025-04-02; stock now at $120.43, -32.2% from 52-week high.

Bonakdarpour sold 5,515 shares (292.4K to 286.9K post-transaction) at $124.78, a modest 1.9% reduction of his holdings executed near a point that was 29.6% below the stock's 52-week high of $177.69. The transaction occurred after the stock had already declined 9.0% in the prior 30 days, placing the sale near a local inflection point. His same-ticker history at ROOT shows that 1 of 5 prior buys achieved a well-timed 90-day outcome (only the 2023-08-22 purchase), suggesting his timing at this specific ticker has been inconsistent. With ROOT trading at a P/E of 31.36 and showing strong annual revenue growth of +158.6%, the stock's sharp recent decline from its 52-week high may reflect profit-taking by the broader market rather than fundamental deterioration, though the sale itself remains a discrete data point in a series of trades without a decisive directional pattern.

ROOT CEO Timm Alexander E. sells 8,497 shares in 2 transactions for $1,070,814.78 on April 1-2, 2025.

CEO Timm Alexander E. executed 2 separate sales totaling 8,497 shares for $1,070,814.78 over April 1-2, 2025, reducing holdings from 185,396 shares to 176,899 shares (a -4.6% reduction). The blended average sale price of $126.02 sits 4.6% above the current price of $120.43 and well below the 52-week high of $177.69. Root's recent fundamentals show strong growth with annual revenue growth of +158.6% and latest quarterly revenue of $305,700,000.00, though the stock is down -32.2% from its 52-week high and -9.0% over the past 30 days. The CEO retains 176,899 shares post-sale, maintaining substantial equity exposure to the company.

10% owner Malka Meyer sells 395,261 shares across 18 transactions for $32.4M, reducing stake to zero; blended average $82.00 vs current $74.99.

Malka Meyer, a 10% owner, executed 18 separate sales totaling 395,261 shares for $32,409,457.02 between November 7–11, 2024, at a blended average price of $82.00. The current stock price is $74.99, representing a 9.5% discount from the 52-week high of $82.90 and within Meyer's transaction price range. However, the filing contains a derivative-conversion flag indicating that Table II derivative securities holdings are not yet populated in the database; Meyer's real position may include options or other derivatives not reflected in the Table I shares-after figure of zero. The sale occurred during a period of strong upward momentum—the stock has gained 75.5% over the prior 30 days and 60.8% over the prior 90 days—and follows five additional sales at ROOT on October 31, 2024. Meyer's cross-ticker track record shows 16 prior sells with an average 30-day return of +17.1%, suggesting her sales have historically preceded further gains, though same-ticker historical outcomes at ROOT are not yet measurable. ROOT is growing revenue at 46.4% annually and currently profitable on a quarterly basis ($22.8M net income), though it remains unprofitable on a full-year basis.

10% owner Malka Meyer sold 50,959 shares (51.0K shares) for $4.3M on 2024-10-31 via 12 separate transactions at prices ranging $70.40–$100.33.

On 2024-10-31, Malka Meyer, a 10% owner at Root, Inc., executed 12 separate open-market sales totaling 50,959 shares for $4,320,550.51 at a blended average price of $84.78. The stock currently trades at $70.96, approximately 14.4% below the 52-week high of $82.90, and the 30-day and 90-day moves are +77.9% and +28.4% respectively. The sale reduced Meyer's holdings from 94,066 shares to 43,107 shares (-54.2% of pre-transaction holdings). Root reported revenue of $305,700,000.00 and net income of $22,800,000.00 for the latest quarter, with annual revenue growth of +46.4%, though the company was unprofitable on a full-year basis. Meyer's cross-ticker insider history shows only 1 prior open-market sale, providing limited precedent for assessing her selling pattern at this ticker. The multi-tranche structure and the spread of transaction prices across the trading day merit observation by investors monitoring major shareholder moves.