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King James Winston, Chief Admin Officer, Gen Couns at Guidewire Software Inc (NYSE:GWRE), sold 7,162 shares of common stock on September 18, 2025, for a total of $1.78 million. The sales occurred at prices ranging from $247.209 to $250.1226. The transaction comes as Guidewire, now valued at $20.77 billion, has seen its stock surge 27.7% over the past six months, significantly outperforming the market.
The transactions involved the sale of shares in four separate transactions. Winston sold 1,878 shares at an average price of $247.209, 1,197 shares at an average price of $248.1553, 1,940 shares at an average price of $249.3535, and 2,147 shares at an average price of $250.1226.
Following the reported transactions, Winston directly owns 38,615 shares of Guidewire Software, Inc.
The sales were executed automatically pursuant to a 10b5-1 trading plan adopted by Winston on October 15, 2024, and amended on April 14, 2025.
In other recent news, Guidewire reported strong fiscal fourth-quarter results, surpassing expectations in revenue, annual recurring revenue (ARR), and non-GAAP operating income. The company achieved an ARR of $1,032 million, exceeding consensus estimates of $1,018 million, supported by 19 cloud deals, including significant agreements with major clients like Liberty Mutual. Following these results, DA Davidson raised its price target for Guidewire to $250, maintaining a Neutral rating, while Oppenheimer increased its target to $300, citing strong cloud growth and maintaining an Outperform rating. Raymond James also raised its price target to $275, highlighting Guidewire’s record bookings and improved outlook.
Goldman Sachs reiterated its Buy rating with a price target of $305, noting growth opportunities from the migration of on-premise customers to cloud-based services. Oppenheimer also maintained its Outperform rating, emphasizing increased customer receptivity to larger migrations, which supports the company’s revised growth projection. These developments reflect a positive sentiment among analysts regarding Guidewire’s performance and future prospects.
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