Michael George Rosenbaum, the Chief Executive Officer of Guidewire Software (NASDAQ: GWRE), sold 1,200 shares of the company’s common stock on February 23, 2026. The shares were disposed of at $125.50 per share, producing a total transaction value of $150,600.
The sale was conducted automatically under a pre-established 10b5-1 trading plan that Rosenbaum adopted on October 14, 2025. After completing the trade, Rosenbaum directly holds 229,543 shares of Guidewire Software.
At the time of the sale, Guidewire’s shares were trading near their 52-week low of $120.37, with the most recent price cited at $122.22. Investors will note the timing of the disposition as the company approaches its fiscal reporting date - Guidewire is scheduled to release earnings on March 5.
Corporate capital actions and analyst moves
Alongside the insider transaction, Guidewire’s board of directors authorized a new $500 million share repurchase program, which the company stated is effective immediately. The board noted that the company’s prior buyback program had been completed after using the remaining $138.2 million that had been authorized in September 2022. Under the new authorization, Guidewire may repurchase common stock either in the open market or through privately negotiated transactions.
Analysts have recently adjusted their stances on Guidewire in the wake of the company’s fiscal first-quarter 2026 results and subsequent share price movement. DA Davidson raised its rating from Neutral to Buy while maintaining a $246 price target. Citizens reiterated a Market Outperform rating and retained a $300 price target.
Valuation commentary and near-term catalyst
InvestingPro analysis referenced in connection with the company indicates that Guidewire appears overvalued at current levels, and users are directed to further tools and metrics for deeper evaluation ahead of the March 5 earnings report, including 17 additional ProTips and comprehensive financial measures.
Taken together, the insider sale under a 10b5-1 plan, the sizable new buyback authorization, and recent analyst rating activity form the immediate backdrop for investors monitoring Guidewire as it approaches its next earnings announcement.
Summary of transaction and corporate actions
- Insider sale: CEO Michael George Rosenbaum sold 1,200 shares on February 23, 2026 at $125.50 per share, totaling $150,600.
- Ownership after sale: Rosenbaum directly owns 229,543 shares.
- Trading context: Shares were trading near a 52-week low of $120.37 and at $122.22 at the time cited.
- Board action: New $500 million repurchase program effective immediately; prior program completed after using remaining $138.2 million authorized in September 2022.
- Analyst moves: DA Davidson upgraded to Buy with a $246 target; Citizens reiterated Market Outperform with a $300 target.