Guidewire Software CEO Michael Rosenbaum sold 1,200 shares of common stock on August 24 for $225,384, according to a filing. The sale was executed at $187.82 per share through a 10b5-1 trading plan established on October 14, 2025.
Following the transaction, Rosenbaum retains direct ownership of 187,776 shares. The stock rose to $191.89 in after-hours trading, extending a six-month gain of 41%. Guidewire’s shares have gained ground despite mixed analyst sentiment and recent earnings results.
Guidewire reported fiscal third-quarter revenue slightly below expectations, though annual recurring revenue (ARR) reached $1.147 billion, up 19% year-over-year. The company’s cloud conversion momentum and AI initiatives continue to draw coverage from multiple analysts.
Wells Fargo maintained an Underweight rating with a $190 price target. Stifel raised its target to $225 and kept a Buy rating, forecasting ARR to exceed expectations by more than $10 million in the fourth quarter. Piper Sandler initiated coverage with an Overweight rating and a $210 target, citing strong subscription revenue growth. Guggenheim initiated with a Buy rating and a $180 target, highlighting Guidewire’s leadership in the Property & Casualty insurance software market.
On the operational front, Germania Mutual Insurance has deployed Guidewire’s AI assistant, ProNavigator, to support underwriting and claims operations, aiming to improve access to company knowledge and documents.
