Michael George Rosenbaum, the Chief Executive Officer of Guidewire Software (NYSE:GWRE), completed a sale of 1,200 shares of the company's common equity on January 20, 2026. The stock was sold at a price point of $156.26 per share, which translates into a total transaction value of $187,512.
Following this disposition, Rosenbaum maintains direct ownership of 235,543 shares in Guidewire Software. Notably, this stock sale was executed automatically pursuant to a pre-established 10b5-1 trading plan that Rosenbaum adopted on October 14, 2025, allowing for systematic sales under specified conditions.
In a related strategic announcement, Guidewire recently launched a new $500 million share repurchase program. This initiative became effective immediately after the company completed its earlier buyback program, where it utilized the remaining $138.2 million authorized in September 2022. The company's board of directors authorized this fresh repurchase plan enabling Guidewire to buy back its common stock through both open market purchases and privately negotiated transactions.
Investor interest is underscored by recent analyst activity. DA Davidson upgraded Guidewire's stock rating from Neutral to Buy, while maintaining a price target of $246. This upgrade follows a notable pullback in the company’s share price, which declined roughly 20% from recent highs after the fiscal first-quarter 2026 earnings report. Additionally, Citizens reiterated its Market Outperform rating with an aggressive price target of $300, reflecting continued confidence in Guidewire's market position and financial strategy.
These developments collectively illustrate a dynamic period for Guidewire Software, reflecting both active insider share transactions and robust capital allocation strategies aimed at enhancing shareholder value.