Insider Trading June 25, 2026 05:43 PM

Pinterest Director Benjamin Silbermann Moves $1.87 Million in Shares Under Pre-Arranged Plan

Insider activity tracks with broader analyst sentiment as Pinterest navigates valuation metrics and regulatory deadlines.

By Priya Menon
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Benjamin Silbermann, a director and significant shareholder of Pinterest, Inc. (NASDAQ:PINS), executed a series of stock sales totaling approximately $1.87 million on June 23 and 24, 2026. The transactions, conducted through a pre-arranged Rule 10b5-1 trading plan established in February 2026, involved the sale of 93,750 Class A Common Stock shares. These sales were preceded by the conversion of an equivalent number of Class B Common Stock shares. The activity occurs as Pinterest maintains a market capitalization of $10.9 billion and reports a gross profit margin nearing 80% over the last twelve months. Despite recent analyst upgrades and positive revenue forecasts, the stock has experienced a 44% decline over the past year and trades 51% below its 52-week high of $39.93. The insider activity takes place against a backdrop of ongoing regulatory compliance requirements and competitive dynamics within the social media sector.

Pinterest Director Benjamin Silbermann Moves $1.87 Million in Shares Under Pre-Arranged Plan
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Key Points

  • Benjamin Silbermann executed sales of 93,750 Class A Common Stock shares totaling approximately $1.87 million through a pre-arranged Rule 10b5-1 plan established in February 2026.
  • Pinterest maintains a market capitalization of $10.9 billion and reported $4.4 billion in revenue over the last twelve months with a gross profit margin nearing 80%.
  • Analysts from UBS, TD Cowen, and Guggenheim have maintained Buy ratings for Pinterest, citing strong U.S. advertising business, AI improvements, and growth drivers in the UCAN region.

Benjamin Silbermann, who serves as a director and holds a 10% ownership stake in Pinterest, Inc. (NASDAQ:PINS), completed the sale of Class A Common Stock valued at approximately $1.87 million during the trading days of June 23 and 24, 2026. These transactions were facilitated under a pre-arranged Rule 10b5-1 trading plan that Mr. Silbermann originally adopted on February 27, 2026. The execution of these sales involved a total of 93,750 shares of Class A Common Stock, with each sale preceded by the conversion of an equal number of Class B Common Stock shares, a standard procedure associated with the liquidation of such holdings.

On June 23, 2026, Mr. Silbermann sold 46,875 shares of Class A Common Stock. This initial tranche included 26,534 shares transacted at prices ranging from $19.14 to $19.99 per share. An additional 20,341 shares were sold on the same day with prices between $20.00 and $20.4350 per share. The following day, June 24, 2026, he executed another sale of 46,875 Class A Common Stock shares, with transaction prices ranging from $19.64 to $20.2150 per share. All reported sales and conversions were processed indirectly through the Benjamin and Divya Silbermann Family Trust.

Following these transactions, Mr. Silbermann's direct holdings include 13,996 shares of Class A Common Stock, which remain subject to vesting requirements. His indirect holdings include 35,455,638 shares of Class B Common Stock held through the Benjamin and Divya Silbermann Family Trust. Additionally, he holds 1,174,715 shares of Class B Common Stock directly. A further 8,762,530 shares of Class B Common Stock are held indirectly through SFTC, LLC. Mr. Silbermann disclaims beneficial ownership of the SFTC, LLC shares except to the extent of his pecuniary interest, if any, through certain immediate family members' interests in The Silbermann 2012 Irrevocable Trust. Each share of Class B Common Stock is convertible into one share of Class A Common Stock.

Pinterest currently maintains a market capitalization of $10.9 billion and has posted revenue of $4.4 billion over the last twelve months, supported by a gross profit margin of nearly 80%. According to InvestingPro analysis, the stock appears undervalued at current levels based on Fair Value calculations. Investors seeking deeper insights can access Pinterest's comprehensive Pro Research Report, one of 1,400+ available on InvestingPro, which transforms complex Wall Street data into actionable intelligence. The stock closed at $19.48 on the relevant date, reflecting a decline of $0.38 or 1.91%. After-hours trading showed a further minor decline to $19.44, down $0.04 or 0.19%.

In other recent news, Pinterest Inc. has been the focus of several analyst updates and strategic developments. UBS raised its price target for Pinterest to $30, maintaining a Buy rating, following the company's recent earnings results. The firm noted an increase in its 2026 revenue forecast by 2.7% and adjusted EBITDA forecast by 6.1%, highlighting Pinterest's investment in Performance+ as a significant driver. Similarly, TD Cowen reiterated a Buy rating with a $38 price target, citing the company's position as a Best Smidcap Idea for 2026 and its growth drivers.

Guggenheim also maintained a Buy rating, setting a $24 price target, and pointed out Pinterest's continued usage growth and strong U.S. advertising business, bolstered by AI improvements. The firm expects revenue growth for the second quarter to be at the high end of the guidance range, with ongoing double-digit growth in the UCAN region. In other developments, Meta Platforms' launch of premium subscription versions of its products has had a ripple effect, with implications for Pinterest and other social media companies. Lastly, the Federal Trade Commission has reminded tech companies, including Pinterest, of the upcoming compliance deadline for the Take It Down Act, which mandates a process for removing intimate images shared without consent.

Risks

  • Pinterest's stock has declined 44% over the past year and remains 51% below its 52-week high of $39.93, indicating significant price volatility and potential valuation concerns.
  • The Federal Trade Commission has reminded tech companies, including Pinterest, of an upcoming compliance deadline for the Take It Down Act, introducing regulatory risk related to content removal processes.
  • Competitive pressures are evident as Meta Platforms' launch of premium subscription versions of its products creates a ripple effect with implications for Pinterest and other social media companies.

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