Benjamin Silbermann

Benjamin Silbermann sells 93,750 shares (93.8K) at avg $19.94 via scheduled 10b5-1 plan; stock down 51.2% from 52-week high

Benjamin Silbermann, Director at Pinterest, executed 3 separate sales totaling 93,750 shares (93.8K shares) for $1,869,601.80 on 2026-06-23 and 2026-06-24 at a blended average price of $19.94 per share, all pursuant to a pre-arranged 10b5-1 trading plan adopted on 2026-02-27. The stock trades at $19.48, down 51.2% from its 52-week high of $39.93. Across his open-market history (all tickers), Silbermann's 20 prior sells averaged a 90-day return of -26.8%, suggesting a historical pattern of selling before recoveries. The sales disposed of his entire non-derivative position; however, he retains 35,455,638 Class B shares through two family trust vehicles, preserving substantial control and economic interest in the company.

Benjamin Silbermann sells 93,750 PINS shares for $1,959,825 via scheduled 10b5-1 plan; retains substantial derivative holdings through family trust.

Benjamin Silbermann, as Director of Pinterest, sold 93,750 shares in two separate transactions on 2026-06-16 and 2026-06-17 at prices of $21.15 and $20.66 respectively, totaling $1,959,825.00 with a blended average price of $20.90. This sale is part of a pre-arranged 10b5-1 trading plan adopted on 2026-02-27, making it scheduled rather than discretionary. While the Form 4 shows zero non-derivative shares post-transaction, the insider retains substantial derivative holdings: Class B Common Stock through the Benjamin and Divya Silbermann Family Trust totaling 35,502,513 and 35,455,638 shares, indicating his significant ongoing economic interest in the company. The stock is currently trading at $20.36, approximately -49.0% from its 52-week high of $39.93, and the insider's historical cross-ticker track record shows an average 90-day return of -26.2% following his prior sells, though same-ticker outcomes on previous PINS sales are mixed with the most recent measurable trade (2025-09-24) showing -25.3% over 90 days.

Benjamin Silbermann (Director) sells 93,750 PINS shares for $2,025,689.07 via scheduled 10b5-1 plan; holds 71,145,651 derivative shares.

Director Benjamin Silbermann completed 2 separate sales totaling 93,750 shares for $2,025,689.07 on June 9–10, 2026, executed under a pre-arranged 10b5-1 trading plan adopted on 2026-02-27. His non-derivative holdings fell to 0 shares post-transaction; however, he retains significant derivative holdings of 71,145,651 Class B shares across two trusts, so this represents a scheduled disposition of a specific share batch rather than a full position liquidation. His prior 5 sales at PINS showed mixed post-sale performance (30-day returns ranging from -2.5% to -12.0%, 90-day returns from -25.3% to -29.9%), though his cross-ticker track record averaged -6.6% over 30 days and -22.8% over 90 days on 20 prior sells. PINS trades at 45.5% below its 52-week high of $39.93, though it has recovered 20.3% over the past 90 days and 4.9% in the last 30 days.

Benjamin Silbermann sells 93,750 shares of PINS across 2 transactions for $1,911,529.69 via scheduled 10b5-1 plan

Benjamin Silbermann (Director) executed two separate sales totaling 93,750 shares for $1,911,529.69 at blended average price $20.39 on June 2–3, 2026, pursuant to a pre-arranged 10b5-1 trading plan adopted February 27, 2026. This sale reduced his non-derivative holdings to zero; however, substantial derivative holdings remain through the Benjamin and Divya Silbermann Family Trust, totaling 71,333,151 shares across two vehicles. His prior sales at PINS have consistently yielded negative 90-day returns: ranging from -25.3% to -29.9%, indicating unfavorable exit pricing relative to subsequent price action. The current stock price of $21.59 stands -45.9% below the 52-week high of $39.93, and the transaction occurred at $20.39, below current levels. The scheduled nature of the transaction (10b5-1 plan) means this sale follows a predetermined schedule rather than discretionary market timing.

Director Benjamin Silbermann sold 102,083 shares (102.1K) at blended $34.86, exiting convertible securities position

Director Benjamin Silbermann executed 2 separate sales totaling 102,083 shares for $3,558,117.13 on 2025-09-24, with transactions priced at $34.86 and $34.85 respectively. This transaction reflects a conversion of derivative securities (underlying position held in Form 4 Table II derivatives, not yet populated), so the zero shares post-transaction does not represent a full exit from his total beneficial holdings. The sales occurred at prices approximately 4.2% above the current market price of $33.45, though the stock has declined 7.2% over the prior 30 days and 16.4% from its 52-week high of $40.00. Silbermann's cross-ticker track record shows 20 prior sells with an average 30-day return of -1.1%, providing limited contextual insight into transaction timing, and his prior same-ticker sales at PINS (5 recent transactions) remain too recent to assess measurable outcomes. The company's fundamentals show revenue of $998,227,000.00 and net income of $38,755,000.00 with 19.4% annual revenue growth, alongside a P/E of 12.21.

Director Benjamin Silbermann sold 102,083 shares (all holdings) for $3,742,804.86 across 3 transactions on 2025-09-17

Benjamin Silbermann executed 3 separate sales totaling 102,083 shares for $3,742,804.86 on 2025-09-17, with transaction prices ranging from $36.49 to $36.80 and a blended average of $36.66. The current stock price is $36.30, modestly below the transaction prices, with the stock up 3.1% over 30 days and 6.1% over 90 days. Silbermann's cross-ticker track record shows 20 prior sells averaging a 0.4% 30-day return, while his prior PINS trades in early September (3 sales on 2025-09-10 and 2 on 2025-09-03) have yet to record measurable outcomes. Given the FLAG notation regarding derivative-conversion activity, this sale represents a transaction involving converted derivative securities rather than a straightforward liquidation of common holdings; investors should review Table II of the Form 4 filing to understand the full derivative position context. The timing of these sales in mid-September, combined with PINS fundamentals showing 19.4% annual revenue growth and a P/E of 13.25, reflects standard insider market activity without clear directional signal.

Director Silbermann executes 3 separate sales totaling 102,083 shares for $3,582,352.27, leaving 0 shares post-transaction.

Silbermann Benjamin, a Director at Pinterest, executed 3 separate open-market sales on 2025-09-10, disposing of 102,083 shares (102.1K shares) for $3,582,352.27 at a blended average price of $35.09. The timing of this filing merits note: the prior 5 same-ticker sales at PINS occurred between 2025-08-20 and 2025-09-03, creating a sustained pattern of directional selling by this insider over three weeks. However, because the FLAG indicates this involves a derivative-conversion transaction, the shares_after count of 0 does not represent a complete position exit—the insider's actual holdings may include unconverted derivative securities held in Form 4 Table II (not yet populated in the database). The company's fundamentals show solid growth (annual revenue growth of +19.4%, P/E of 12.76) and recent profitability ($38,755,000.00 net income in the latest quarter), providing context for evaluating whether the sales reflect operational concern or ordinary management of equity compensation. Stock price at execution ($35.09 blended) is near current levels ($34.96) and not yet at the 52-week high of $40.00, leaving room to assess the timing of these sales in retrospect.

Director Benjamin Silbermann sold 102,083 shares at $37.04 on 2025-09-03 for $3.8M; post-derivative conversion.

Benjamin Silbermann, as Director of Pinterest, executed 2 separate sales totaling 102,083 shares for $3,780,819.32 at a blended average price of $37.04 on 2025-09-03. The filing is flagged as a derivative-conversion transaction, meaning the insider's actual position extends beyond the Table I shares shown here (which report zero post-transaction holdings), and the full picture of his economic interest requires review of Table II derivative securities. The stock currently trades at $37.12, just 8 cents above the sale price, with 52-week performance ranging from $24.21–$40.00; the insider sold within 7.2% of the 52-week peak. Silbermann's cross-ticker track record shows 20 prior open-market sales averaging a +2.5% 30-day return after the sale, whereas his 5 recent same-ticker trades at PINS (Aug 13, Aug 20, Aug 27, and now Sept 3) show a pattern of sequential dispositions over a 3-week window, none yet measurable at the 90-day mark. The timing of this sale, occurring near the stock's 52-week high and during a period of strong valuation (P/E 13.55) and solid fundamentals (Revenue $998.2M, +19.4% annual growth, Net income $38.8M), coupled with the concentrated nature of the recent sales activity, warrants investor attention to the underlying economic motivation and whether the conversion-based nature of this filing masks a broader de-risking pattern.

Director Benjamin Silbermann sold 102,083 shares of PINS at $36.03 for $3.7M on 2025-08-27; post-transaction holdings reflect only derivative positions.

Benjamin Silbermann, Director at Pinterest, executed 2 separate sales totaling 102,083 shares for $3,677,902.79 at $36.03 per share on 2025-08-27. The Form 4 filing indicates a derivative-conversion transaction; Table I shows zero shares post-transaction, but per the FLAG, the insider's real position lives in derivative securities (Table II), which means this does not represent a complete exit from the company. The stock has declined 4.2% over 30 days and 8.2% from its 52-week high, though it is up 18.0% over 90 days. His cross-ticker track record shows 20 prior open-market sells with an average 30-day return of +2.4%, though same-ticker measurable outcomes at PINS are limited: only the 2025-07-23 sale shows a 30-day result of -6.2%. This sale should be understood as a structured conversion/settlement of derivative positions rather than a discretionary reduction in his overall stake.

Director Silbermann sells 102,083 shares at $34.96; post-transaction holdings show conversion of derivative securities

Benjamin Silbermann (Director) executed 2 separate sales totaling 102,083 shares for $3,569,087.10 at $34.96 per share on 2025-08-20. The Form 4 contains a derivative-conversion transaction; Table I shows zero shares post-transaction, but the insider's actual position includes derivative securities in Table II (not yet populated in the database), so this sale should not be characterized as a complete exit. The stock currently trades at $34.87, near the transaction price but 12.8% below its 52-week high. The timing context is relevant: across 5 prior trades at PINS, outcomes on 4 are not yet measurable, and the earliest measurable prior sale (2025-07-16) showed a -0.6% 30-day return with 90-day outcome pending. The insider's cross-ticker track record shows 20 prior sells with an average 30-day return of +4.1%, but PINS-specific timing patterns remain inconclusive.