Guidewire Software (GWRE) CEO Rosenbaum Sells $225K of Stock

On October 26, 2026, Michael George Rosenbaum, the Chief Executive Officer of Guidewire Software, Inc. (GWRE), sold 1,200 shares for $224,628. The transaction was reported in a Form 4 filing with the SEC. He sold these shares at a price of $187.19 each, a planned sale under a Rule 10b5-1 plan.

Rosenbaum's sale reduced his total ownership to 273,666 shares, which reflects a 0.44% decrease in his stake. This sale follows a pattern of insider trades at Guidewire, as other executives have also sold shares recently.

GWRE Guidewire Software, Inc.

$189 ▲ +0.73% year to date

1M 3M YTD

Daily close · Oct 23, 2026

Other Institutional Activity in Guidewire Software

BAMCO Inc. increased its stake in Guidewire by 2,396,894 shares, bringing its total to 8,994,456 shares valued at about $1.65 billion. Conversely, Linonia Partnership LP reduced its holdings by 717,679 shares, ending with 6,933,483 shares worth approximately $1.28 billion. Darsana Capital Partners, LP trimmed its position by 196,000 shares, now holding 3,804,000 shares valued at about $699.8 million. Massachusetts Financial Services Co. decreased its stake by 966,232 shares, leaving it with 2,028,908 shares worth around $373.2 million.

Guidewire Software, Inc. Stock Down 3.0%

On October 26, 2026, Guidewire shares closed at $183.96, which is about equal to the recent trading price. The stock is currently above its 50-day moving average by 9.5% and above its 200-day moving average by 23.3%. However, it is below its 52-week high of $255.89 by about 28.1%.

Recent Earnings

Guidewire reported trailing twelve-month revenue of approximately $1.48 billion, with a year-over-year revenue growth of 15.3%. The next earnings report is scheduled for December 3, 2026.

Insider Buying and Selling at Guidewire Software, Inc.

Recently, several insiders have sold shares of Guidewire. On October 9, 2026, James Winston King, Chief Admin Officer and General Counsel, sold 9,187 shares at $168.00 each, totaling about $1.54 million. Michael Rosenbaum also sold shares on earlier dates: 1,200 shares on October 12 for about $202,764 and again on October 19 for approximately $201,480. Additionally, John P. Mullen, the President, sold 5,400 shares on October 20 for around $999,000.

Analysts Set New Price Targets

On September 4, 2026, Citigroup maintained a Neutral rating on Guidewire with a price target of $181. Oppenheimer also maintained an Outperform rating with a target of $210, while DA Davidson kept its Buy rating and target at $222. The consensus recommendation among analysts is to buy, with a mean price target of $213.29.

About Guidewire Software

Guidewire Software, Inc. specializes in providing software solutions for property and casualty insurers. Its products help insurers manage their operations more efficiently, covering areas like policy management, claims processing, and underwriting. This recent insider selling may reflect the company's ongoing adjustments in leadership and strategy.

Bottom Line

Investors should keep an eye on the upcoming earnings report on December 3, 2026, for further insights into Guidewire's performance. The recent insider sales, including Rosenbaum's, highlight ongoing executive activity as the company navigates its business landscape.