Insider Selling: Guidewire Software (NYSE:GWRE) CEO Sells $175,104.00 in Stock

Guidewire Software, Inc. (NYSE:GWRE) CEO Michael Rosenbaum sold 1,200 shares of the business’s stock in a transaction on Monday, September 21st. The stock was sold at an average price of $145.92, for a total value of $175,104.00. Following the transaction, the chief executive officer directly owned 279,666 shares in the company, valued at $40,808,862.72. This trade represents a 0.43% decrease in their position. The transaction was disclosed in a legal filing with the SEC, which can be accessed through the SEC website. The transaction was executed under a pre-arranged Rule 10b5-1 trading plan. The sale was made to cover tax withholding obligations related to the vesting of equity awards.

Michael George Rosenbaum also recently made the following trade(s):

• On Thursday, September 17th, Michael Rosenbaum sold 72,290 shares of Guidewire Software stock. The stock was sold at an average price of $144.47, for a total value of $10,443,736.30.
• On Monday, September 14th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $145.87, for a total transaction of $175,044.00.
• On Tuesday, September 8th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $160.52, for a total transaction of $192,624.00.
• On Monday, August 31st, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $204.44, for a total transaction of $245,328.00.
• On Monday, August 24th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $187.82, for a total transaction of $225,384.00.
• On Monday, August 17th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $172.88, for a total transaction of $207,456.00.
• On Monday, August 10th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $169.50, for a total transaction of $203,400.00.
• On Monday, August 3rd, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $155.92, for a total transaction of $187,104.00.
• On Monday, July 27th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $142.31, for a total transaction of $170,772.00.
• On Monday, July 13th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $138.47, for a total value of $166,164.00.

Guidewire Software Trading Up 1.8%

Shares of Guidewire Software stock opened at $153.10 on Thursday. The stock has a 50 day moving average of $164.69 and a 200 day moving average of $147.40. The company has a debt-to-equity ratio of 0.57, a quick ratio of 1.79 and a current ratio of 1.79. The firm has a market capitalization of $12.75 billion, a price-to-earnings ratio of 93.93 and a beta of 0.97. Guidewire Software, Inc. has a fifty-two week low of $102.30 and a fifty-two week high of $255.89.

Guidewire Software (NYSE:GWRE) last posted its earnings results on Thursday, September 3rd. The technology company reported $0.99 EPS for the quarter, beating analysts’ consensus estimates of $0.93 by $0.06. Guidewire Software had a return on equity of 12.66% and a net margin of 9.44%.The company had revenue of $411.09 million for the quarter, compared to the consensus estimate of $402.61 million. During the same quarter in the previous year, the business earned $0.84 earnings per share. The company’s revenue for the quarter was up 15.3% on a year-over-year basis. As a group, research analysts predict that Guidewire Software, Inc. will post 2.46 earnings per share for the current year.

Analyst Ratings Changes

A number of research analysts have commented on the stock. Citigroup upped their target price on shares of Guidewire Software from $137.00 to $181.00 and gave the company a “neutral” rating in a research report on Friday, September 4th. Royal Bank Of Canada reiterated an “outperform” rating and set a $215.00 price target on shares of Guidewire Software in a research report on Friday, September 4th. Guggenheim boosted their price target on shares of Guidewire Software from $180.00 to $210.00 and gave the company a “buy” rating in a research note on Thursday, August 27th. The Goldman Sachs Group decreased their price objective on shares of Guidewire Software from $255.00 to $225.00 and set a “buy” rating on the stock in a report on Friday, June 5th. Finally, Wells Fargo & Company increased their price objective on shares of Guidewire Software from $190.00 to $195.00 and gave the stock an “overweight” rating in a research report on Friday, September 4th. Twelve investment analysts have rated the stock with a Buy rating and four have issued a Hold rating to the company’s stock. Based on data from MarketBeat, the stock presently has a consensus rating of “Moderate Buy” and a consensus price target of $216.23.

Institutional Investors Weigh In On Guidewire Software

Several large investors have recently added to or reduced their stakes in GWRE. QRG Capital Management Inc. boosted its position in Guidewire Software by 5.1% in the 2nd quarter. QRG Capital Management Inc. now owns 5,280 shares of the technology company’s stock valued at $650,000 after buying an additional 258 shares during the period. Tidal Investments LLC increased its position in shares of Guidewire Software by 20.5% during the second quarter. Tidal Investments LLC now owns 11,134 shares of the technology company’s stock worth $1,370,000 after acquiring an additional 1,895 shares during the period. Integrated Wealth Concepts LLC purchased a new stake in shares of Guidewire Software during the second quarter worth $53,000. Baird Financial Group Inc. raised its stake in shares of Guidewire Software by 86.8% in the second quarter. Baird Financial Group Inc. now owns 2,811 shares of the technology company’s stock valued at $346,000 after acquiring an additional 1,306 shares in the last quarter. Finally, Nykredit A S acquired a new stake in shares of Guidewire Software in the second quarter valued at $360,000.

Trending Headlines about Guidewire Software

Here are the key news stories impacting Guidewire Software this week:

• Positive Sentiment: Cloud and AI growth support the investment case. Guidewire ended fiscal 2026 with annual recurring revenue (ARR) growth of 19%, while cloud ARR rose 35%. Contracted backlog also provides visibility into fiscal 2027. Investors view the company’s cloud migration opportunity and AI-enabled insurance tools as key long-term growth drivers. Can Guidewire Software Maintain Its Robust ARR Growth Momentum?
• Positive Sentiment: Recent earnings exceeded expectations. Guidewire reported quarterly EPS of $0.99 versus the $0.93 consensus estimate and revenue of $411.09 million versus expectations of $402.61 million. Revenue increased 15.3% year over year, reinforcing confidence in demand for its insurance software platform. Guidewire Software Stock Gains as Earnings Beat Estimates
• Positive Sentiment: Analysts remain broadly constructive, with a consensus “Moderate Buy” rating and an average price target of $216.23, substantially above the recent trading level. Several firms have also raised or maintained targets near $200 or higher.
• Neutral Sentiment: Despite the growth outlook, commentary suggests GWRE may be fairly valued after investors priced in much of its cloud and AI opportunity. With a price-to-earnings ratio above 90, further gains may depend on sustained ARR expansion and improving profitability. Guidewire Stock May Be Fairly Priced on Cloud and AI Growth
• Negative Sentiment: Multiple executives sold shares, including CEO Michael Rosenbaum, who sold 72,290 shares, and CFO Jeffrey Cooper and James Winston King, who also reported sizable sales. The transactions were conducted under Rule 10b5-1 plans and included sales for tax withholding, reducing their bearish significance, but the volume can still weigh on sentiment. Guidewire Executive Stock Sale

About Guidewire Software

Guidewire Software, Inc (NYSE: GWRE) provides cloud-based software and technology services for the property and casualty insurance industry. Its solutions help insurers manage core operations, modernize legacy systems, improve customer engagement and use data to support underwriting and claims decisions.

The company’s principal platform, InsuranceSuite, includes applications such as PolicyCenter for policy administration, BillingCenter for billing and payments, and ClaimCenter for claims management.