Khozema Shipchandler, CEO of Twilio Inc (NASDAQ:TWLO), sold approximately $5.97 million worth of Class A Common Stock on May 26, 2026. The transactions followed employee stock option exercises and were executed under a pre-arranged 10b5-1 trading plan.
Shipchandler disposed of 32,158 shares at weighted average prices ranging from $180.70 to $188.00 per share. The stock currently trades at $184.60, near its 52-week high of $203.71, after a strong 54% gain over the past year.
Prior to the sales, Shipchandler acquired the same number of shares through employee stock option exercises at $76.63 per share, totaling $2,464,267. The options were fully vested and exercisable.
Both the option exercises and subsequent sales were carried out under a 10b5-1 plan established on February 18, 2026.
Following these transactions, Shipchandler directly holds 235,542 shares, including Restricted Stock Units (RSUs). Bond.az data reveals management has been aggressively buying back shares, and the stock appears overvalued based on fair value metrics.
In other news, Twilio reported Q1 2026 earnings exceeding expectations, with EPS of $1.50 on revenue of $1.41 billion. The company also unveiled new platform capabilities.
