Insider Trading July 15, 2026 06:01 PM

Pinterest Executive Silbermann Executes $2.1 Million Share Sale Under Pre-Arranged Plan

Director and major shareholder liquidates 93,750 Class A shares via Rule 10b5-1 mechanism as stock trades near 52-week lows, while analyst community maintains positive outlook on AI-driven ad growth and regulatory compliance.

By Nina Shah
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Benjamin Silbermann, serving as both a Director and a significant 10% shareholder of Pinterest, Inc. (NASDAQ:PINS), has executed a substantial liquidation of company equity. According to recent Securities and Exchange Commission (SEC) documentation, Silbermann sold a total of 93,750 shares of Pinterest’s Class A Common Stock. This transaction resulted in a combined monetary value of $2,122,420. The divestment was carried out over two consecutive trading days, specifically July 14 and July 15, 2026. These sales were facilitated through a pre-arranged Rule 10b5-1 trading plan, which was originally established on February 27, 2026. This sale activity occurs against a backdrop of Pinterest’s stock performance, which has declined by 35% over the trailing twelve months, currently trading at $23.67. Despite this recent price weakness, analytical assessments from InvestingPro suggest the stock may be trading below its intrinsic worth, with a calculated Fair Value of $32.13. This valuation places Pinterest among the opportunities identified on the platform’s list of most undervalued stocks. Furthermore, data from InvestingPro indicates that Pinterest maintains a

Pinterest Executive Silbermann Executes $2.1 Million Share Sale Under Pre-Arranged Plan
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Key Points

  • Benjamin Silbermann liquidated 93,750 Class A shares valued at $2.1 million via a Rule 10b5-1 plan established in February 2026, executed on July 14 and 15, 2026.
  • Pinterest stock has declined 35% over the past year, trading at $23.67, though InvestingPro analysis suggests a fair value of $32.13 and a "GREAT" financial health score of 3.14.
  • Analysts from Guggenheim, TD Cowen, and DA Davidson maintain positive outlooks, citing AI-driven advertising improvements, user growth, and strong mid-cap potential for 2026.

Benjamin Silbermann, serving as both a Director and a significant 10% shareholder of Pinterest, Inc. (NASDAQ:PINS), has executed a substantial liquidation of company equity. According to recent Securities and Exchange Commission (SEC) documentation, Silbermann sold a total of 93,750 shares of Pinterest’s Class A Common Stock. This transaction resulted in a combined monetary value of $2,122,420. The divestment was carried out over two consecutive trading days, specifically July 14 and July 15, 2026. These sales were facilitated through a pre-arranged Rule 10b5-1 trading plan, which was originally established on February 27, 2026. This sale activity occurs against a backdrop of Pinterest’s stock performance, which has declined by 35% over the trailing twelve months, currently trading at $23.67. Despite this recent price weakness, analytical assessments from InvestingPro suggest the stock may be trading below its intrinsic worth, with a calculated Fair Value of $32.13. This valuation places Pinterest among the opportunities identified on the platform’s list of most undervalued stocks. Furthermore, data from InvestingPro indicates that Pinterest maintains a "GREAT" financial health score of 3.14 and holds more cash than debt on its balance sheet, according to InvestingPro data, which offers 10 additional ProTips for deeper analysis.

On July 14, Mr. Silbermann sold 46,875 shares of Class A Common Stock. The shares were sold in multiple transactions at prices ranging from $22.0300 to $22.4950 per share, with a weighted average sale price of $22.2503. The following day, July 15, he sold an additional 46,875 shares. These transactions had prices ranging from $22.7000 to $23.4700 per share, with a weighted average sale price of $23.028. All sales were conducted indirectly through the Benjamin and Divya Silbermann Family Trust.

In connection with these sales, an equal number of Class B Common Stock shares were converted into Class A Common Stock. Each share of Class B Common Stock is convertible into one share of Class A Common Stock, either at the holder’s option or automatically upon transfer, as specified in the company’s Certificate of Incorporation.PinterestFollowAnalyze PINSIncluded in our AI-picked strategies·Review strategies23.67▲+1.06(+4.69%)Closed·15:59:59·USD23.61▼-0.07(-0.30%)After Hours·18:11:111D1W1M6M1Y5YMaxCreated with Highcharts 11.4.814:0015:0016:0017:0018:0019:0022.52323.5Analyze PINSFollowing these transactions, Mr. Silbermann’s direct holdings of Class A Common Stock amount to 13,996 shares, which are subject to vesting requirements. His indirect holdings of Class B Common Stock through the Benjamin and Divya Silbermann Family Trust total 35,080,638 shares, and he directly holds 1,174,715 shares of Class B Common Stock. Additionally, SFTC, LLC, an entity for which Mr. Silbermann disclaims beneficial ownership except to the extent of his pecuniary interest through certain immediate family members, holds 8,762,530 shares of Class B Common Stock.

In other recent news, Pinterest Inc has been the focus of several analyst reports and developments. Guggenheim reiterated its Buy rating on Pinterest, highlighting the company’s AI-driven improvements in its advertising business and consistent global user growth. The firm expects revenue growth to remain at the high end of the guidance range for the second quarter. Meanwhile, TD Cowen also maintained its Buy rating, citing Pinterest as a top mid-cap idea for 2026, driven by strong advertising revenue growth. DA Davidson initiated coverage with a Buy rating, emphasizing Pinterest’s consistent engagement growth over the past ten quarters. Additionally, Pinterest’s shares experienced a rise following news of Meta Platforms launching premium subscription versions of its social media offerings. This development could have implications for the broader social media landscape. Lastly, the Federal Trade Commission reminded technology companies, including Pinterest, of the upcoming compliance deadline for the Take It Down Act, which addresses the removal of non-consensual intimate images.

Risks

  • Pinterest faces an upcoming compliance deadline for the Take It Down Act regarding the removal of non-consensual intimate images, as reminded by the Federal Trade Commission.
  • The stock has experienced significant price depreciation, down 35% over the past year, which may reflect broader market sentiment or valuation adjustments despite analyst optimism.
  • Potential competitive pressures in the social media landscape may arise from Meta Platforms' launch of premium subscription versions of its social media offerings.

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