Guidewire Software (GWRE) Insider Winston Sells $1.5M of Stock

King James Winston, the Chief Admin Officer and General Counsel at Guidewire Software, Inc. (NYSE: GWRE), sold 9,187 shares on October 9, 2026, for about $1.54 million at a price of $168.00 each. This planned sale comes after Winston had previously sold shares in June 2026.

Inside King James Winston's Trade

Winston's recent transaction adds to his history of selling shares, having previously sold 999 shares on June 16, 2026. His recent sale reflects a continued strategy to manage his holdings.

Other Institutional Activity in Guidewire

Several other institutional investors have also adjusted their positions in Guidewire. BAMCO Inc. increased its holdings by 2,396,894 shares, bringing its total to 8,994,456 shares worth about $1.52 billion. Meanwhile, Blackrock Inc. reduced its stake by 417,874 shares, ending with 8,909,665 shares valued at approximately $1.50 billion. Linonia Partnership LP and Vanguard Portfolio Management LLC also trimmed their positions, indicating varied strategies among investors in the company.

Guidewire Software, Inc. Stock Down 5.1%

As of October 16, 2026, Guidewire shares recently traded around $166.84, which is about equal to its 50-day moving average of $166.97. The stock is currently below its 52-week high of $255.89, reflecting a 34.8% decline from that peak. The shares are above their 52-week low of $102.30, showing a 63.1% gain from that level.

Recent Earnings

In its latest earnings report, Guidewire generated $1.48 billion in revenue over the trailing twelve months, with a net margin of 9.4% and a return on equity of 10.5%. The next earnings report is scheduled for December 3, 2026, which will provide further insights into the company’s performance.

Insider Buying and Selling at Guidewire Software, Inc.

In addition to Winston's recent sale, other insiders at Guidewire also sold shares on June 16, 2026. CEO Michael Rosenbaum sold 5,830 shares for $692,254.20, and CFO Jeffrey Elliott Cooper sold 2,594 shares valued at $308,011.56. These sales were not planned under Rule 10b5-1.

Analysts Set New Price Targets

Analysts maintain a positive outlook on Guidewire, with Citigroup holding a Neutral rating and a target price of $181.00 as of September 4, 2026. Oppenheimer and DA Davidson both have Buy ratings, with targets of $210.00 and $222.00, respectively, indicating confidence in the company's growth potential.

About Guidewire Software, Inc.

Guidewire Software, Inc. provides software solutions for property and casualty insurers globally. Its offerings include the Guidewire InsuranceSuite, which encompasses applications for policy management, claims, billing, pricing, and underwriting. The recent insider sales coincide with a period of strategic adjustment for the company.

Bottom Line

Investors should watch for Guidewire's upcoming earnings date on December 3, 2026, for insights into its financial performance. With ongoing adjustments from insiders and institutional investors, the stock's performance will be closely monitored in the coming weeks.