PINS PINTEREST, INC. Insider Trading

Silbermann sells 93,750 shares via scheduled 10b5-1 plan for $2.1M; retains 70,208,151 derivative shares through family trust

Benjamin Silbermann, Director of Pinterest, executed 2 separate sales totaling 93,750 shares for $2,122,420.31 on 2026-07-14 and 2026-07-15 under a pre-arranged 10b5-1 trading plan adopted on 2026-02-27. This is a scheduled, non-discretionary transaction. The sales reduce his non-derivative holdings to 0 shares, but he retains substantial derivative holdings through the Benjamin and Divya Silbermann Family Trust comprising 35,127,513 and 35,080,638 shares. His cross-ticker track record shows 20 prior sells with an average 90-day return of -26.6%, though all 5 of his same-ticker PINS transactions from 2026-06-24 through 2026-07-08 have not yet reached measurable outcome windows. The current stock price of $23.68 trades at -40.7% from the 52-week high of $39.93, positioning these sales within a period of significant price depreciation.

Director Benjamin Silbermann sells 93,750 shares for $2,102,507.82 via scheduled 10b5-1 plan; retains 70,395,651 derivative shares.

Benjamin Silbermann (Director) executed 2 separate sales totaling 93,750 shares for $2,102,507.82 on July 7-8, 2026, at a blended average price of $22.43. This transaction was conducted under a pre-arranged 10b5-1 trading plan adopted on 2026-02-27, meaning it was scheduled and not discretionary. While his non-derivative holdings reached 0 post-transaction, the insider retains substantial derivative holdings through Class B Common Stock vehicles totaling 70,395,651 shares, so this represents a scheduled rebalancing of his non-derivative portion rather than a complete position exit. The current stock price of $22.68 is -43.2% from the 52-week high of $39.93, and his cross-ticker track record shows average 90-day returns of -26.6% following his 20 prior sales.

Pinterest Director Benjamin Silbermann makes 2 scheduled sales of 93,750 shares (~$2.0M) at blended avg $21.55 under 10b5-1 plan.

Benjamin Silbermann, Director at Pinterest, executed 2 separate sales totaling 93,750 shares for $2,019,881.25 — one of 46,875 shares at $21.45 and one of 46,875 shares at $21.64 — under a 10b5-1 trading plan adopted on 2026-02-27, making these scheduled rather than discretionary transactions. This filing is part of a broader pattern of recent activity at PINS, with 5 prior sales on record dating back to 2026-06-16, though none of those same-ticker trades yet have measurable 30-day or 90-day outcomes. Across his cross-ticker open-market history, Silbermann's 20 prior sells show an avg 30d return of -9.0% and avg 90d return of -26.6% for the stock following those trades. PINS currently trades at $22.07, which is -44.7% from its 52-week high of $39.93, while posting +21.4% growth over the prior 90 days and annual revenue growth of +15.8%.

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.

CLO Wanjiku Juanita Walcott sold 27,337 PINS shares at $20.46 under 10b5-1 plan; retains 724,673 shares post-sale.

This sale of 27,337 shares (27.3K shares) at $20.46 is part of a pre-arranged 10b5-1 trading plan adopted on 2026-02-26, making it a scheduled transaction rather than a discretionary decision by Walcott. At current price of $20.87, the stock trades 47.7% below its 52-week high of $39.93, though it has recovered 3.2% over the past 30 days and 7.7% over 90 days. The insider retains substantial holdings of 724,673 shares (724.7K shares) post-transaction. This is a routine portfolio management activity under an established trading plan, with no discretionary timing element to assess.

Chief Business Officer Brown Leonard sells ~61k shares of Pinterest for $1.27M in large single transaction.

Chief Business Officer Brown Claude Leonard sold a significant portion of his holdings in a single transaction at a price below the current market level. The timing is notable: the stock is trading well below its recent highs and has recovered modestly from its lows, yet Leonard chose to sell rather than hold. Beneath the surface, the company remains fundamentally profitable with solid revenue growth, though the latest quarter showed a net loss—a potential headwind that may have factored into the sale. Without visibility into Leonard's prior trading history or broader insider activity, this transaction reads as a standard portfolio reduction by an executive, though the sale size and choice of timing during a recent recovery phase warrants watching whether additional selling emerges from other company leaders.

CFO Julia Brau Donnelly sold 22,821 PINS shares at $25.86; stock down 35.3% from 52-week high.

CFO Julia Brau Donnelly executed an open-market sale of 22,821 shares at $25.86 on 2025-12-24, reducing her holdings from 563,179 to 540,358 shares. The transaction totaled $590,098.57, representing a 4.1% reduction in her position at a price 35.3% below the 52-week high of $40.00. At PINS specifically, her prior 5 trades show a 3-of-5 well-timed pattern at the 90-day horizon—half her sales preceded subsequent declines. The current stock trades at $25.88, essentially flat to the sale price, and Pinterest's fundamentals remain solid with $1.0B quarterly revenue, $92.1M net income, and 19.4% annual revenue growth paired with a 9.45 P/E. While the magnitude of the sale is modest relative to her total holdings and her same-ticker trade history demonstrates mixed timing acuity, the transaction warrants standard monitoring given her CFO-level access and the stock's recent 19.6% decline over the past 90 days.