Pinterest co-founder Benjamin Silbermann sells $1.8 million in shares under pre-planned arrangement
The Executive Chairman of Pinterest has offloaded 93,750 shares of Class A common stock, a move executed under a trading plan adopted earlier this year to facilitate estate planning and asset management.
Benjamin Silbermann, co-founder and Executive Chairman of Pinterest, has sold 93,750 shares of the company’s Class A common stock for approximately $1.8 million. According to a recent SEC Form 4 filing, the transactions were executed on 15 and 16 September 2026, with a weighted average sale price of $18.93 per share.
The sale was carried out under a pre-authorized Rule 10b5-1 trading plan adopted on 27 February 2026. This framework allows insiders to establish a predetermined schedule for stock sales, removing individual discretion from the timing of the transaction. To facilitate the liquidation, Silbermann converted Class B shares to Class A, as Class B shares generally require conversion before they can be sold on the public market.
Following the transaction, Silbermann retains 13,996 Class A shares directly. However, his overall exposure to the company remains substantial through derivative interests. These include approximately 1.2 million shares held directly and roughly 77.7 million shares held indirectly through SFTC, LLC. This entity is owned by The Silbermann 2012 Irrevocable Trust, a structure commonly used by executives for long-term estate planning and asset management rather than short-term market speculation.
The sale occurred against a backdrop of significant stock price volatility. As of the transaction date, Pinterest shares had returned -49 per cent, closing at $18.65 on 16 September 2026. Despite the decline, the company reported trailing twelve-month revenue of $4.6 billion and net income of $248.9 million. In the first half of 2026, revenue rose by 18 per cent annually, although the company returned to losses as it invested in its business.
Silbermann’s move may appear notable given his status as the former CEO and co-founder, but the pre-planned nature of the sale suggests a strategic rather than reactive approach. With a price-to-sales ratio of 2.6, well below the 17 recorded five years ago, the stock is trading at a significant discount to its historical valuation.
The filing highlights the continued use of 10b5-1 plans by corporate insiders to manage liquidity while maintaining long-term investment positions. For investors, the distinction between direct share holdings and derivative interests through trust structures is critical to understanding the true scale of an executive’s commitment to the firm.
