Michael George Rosenbaum, Chief Executive Officer of Guidewire Software Inc (NYSE: GWRE), sold 1,200 shares of the company's common stock on January 26, 2026. The shares changed hands at a price of $160.32 per share, producing total proceeds of $192,384.
At the time of the transaction, Guidewire's shares were trading close to their 52-week low of $154.50, following a 28.36% decline in the prior six months. After completing the sale, Rosenbaum retained direct ownership of 234,343 shares of Guidewire common stock.
The CEO's sale was processed automatically under a pre-arranged 10b5-1 trading plan that Rosenbaum adopted on October 14, 2025. The filing indicates the trade was not a discretionary one-off transaction but part of an established plan to govern insider sales.
Independent valuation analysis referenced in the filings notes that InvestingPro assesses GWRE as trading above its Fair Value, while a consensus of analysts continues to rate the stock a Buy. Published price targets for the company's shares span from $160 to $300, and InvestingPro points to a Pro Research Report offering expanded coverage of Guidewire as part of its universe of more than 1,400 U.S. equities.
In a separate corporate development, Guidewire disclosed a new share repurchase program with an authorization of $500 million, effective immediately. The announcement follows the completion of the company's prior buyback program, which had exhausted the remaining $138.2 million that had been authorized in September 2022. Guidewire's board of directors approved the fresh buyback, permitting the company to repurchase common stock through a variety of means.
Analyst activity around Guidewire has also shifted in recent sessions. DA Davidson upgraded its rating on the stock from Neutral to Buy and maintained a price target of $246. The upgrade came after the shares experienced a roughly 20% pullback following the release of Guidewire's fiscal first-quarter 2026 results. Separately, Citizens reiterated a Market Outperform rating with a $300 price target.
According to the company's filings and the analyst notes, these developments - the insider sale under a 10b5-1 plan, the $500 million repurchase program, and the analyst rating changes - coincided with a period of relative stability in the share price in response to the disclosures.
Summary of the key factual points:
- Rosenbaum sold 1,200 shares on January 26, 2026, at $160.32 per share, totaling $192,384.
- The sale was executed under a 10b5-1 plan adopted October 14, 2025.
- Rosenbaum directly holds 234,343 shares after the transaction.
- Guidewire launched a new $500 million share repurchase program; prior program had $138.2 million remaining as of September 2022 and was completed.
- Analyst actions include a DA Davidson upgrade to Buy with a $246 target and Citizens reiterating Market Outperform with a $300 target; consensus Buy and price targets range from $160 to $300 according to InvestingPro.