Guidewire Software (NYSE:GWRE) CEO Sells $10,443,736.30 in Stock

Guidewire Software, Inc. (NYSE:GWRE) CEO Michael Rosenbaum sold 72,290 shares of the stock in a transaction dated Thursday, September 17th. The shares were sold at an average price of $144.47, for a total value of $10,443,736.30. Following the transaction, the chief executive officer owned 280,866 shares in the company, valued at $40,576,711.02. This trade represents a 20.47% decrease in their ownership of the stock. The sale was disclosed in a legal filing with the SEC, which is available at this hyperlink. 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 Monday, September 21st, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $145.92, for a total transaction of $175,104.00.
• 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 shares were sold at an average price of $204.44, for a total value of $245,328.00.
• On Monday, August 24th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $187.82, for a total value 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 value of $207,456.00.
• On Monday, August 10th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $169.50, for a total value of $203,400.00.
• On Monday, August 3rd, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $155.92, for a total value of $187,104.00.
• On Monday, July 27th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $142.31, for a total value 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 transaction of $166,164.00.

Guidewire Software Trading Up 1.8%

Shares of GWRE opened at $153.10 on Thursday. The stock has a market capitalization of $12.75 billion, a P/E ratio of 93.93 and a beta of 0.97. Guidewire Software, Inc. has a twelve month low of $102.30 and a twelve month high of $255.89. The company has a quick ratio of 1.79, a current ratio of 1.79 and a debt-to-equity ratio of 0.57. The firm has a fifty day simple moving average of $164.69 and a two-hundred day simple moving average of $147.40.

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

Analyst Upgrades and Downgrades

GWRE has been the topic of several research analyst reports. DA Davidson reissued a “buy” rating and set a $222.00 target price on shares of Guidewire Software in a research note on Friday, September 4th. Stifel Nicolaus cut their price target on shares of Guidewire Software from $225.00 to $200.00 and set a “buy” rating on the stock in a report on Friday, June 5th. Citizens Jmp reissued a “market outperform” rating and set a $220.00 price objective on shares of Guidewire Software in a research report on Friday, September 4th. The Goldman Sachs Group decreased their price objective on shares of Guidewire Software from $255.00 to $225.00 and set a “buy” rating for the company in a report on Friday, June 5th. Finally, Oppenheimer raised their target price on shares of Guidewire Software from $200.00 to $210.00 and gave the stock an “outperform” rating in a research report on Friday, September 4th. Twelve analysts have rated the stock with a Buy rating and four have issued a Hold rating to the stock. According to MarketBeat, the company has a consensus rating of “Moderate Buy” and a consensus price target of $216.23.

Hedge Funds Weigh In On Guidewire Software

Several large investors have recently made changes to their positions in GWRE. Bamco Inc. NY bought a new position in Guidewire Software during the 2nd quarter valued at approximately $1,106,768,000. Linonia Partnership LP purchased a new stake in shares of Guidewire Software in the second quarter worth $853,165,000. Route One Investment Company L.P. purchased a new position in Guidewire Software in the second quarter worth about $227,564,000. Van ECK Associates Corp purchased a new stake in shares of Guidewire Software during the second quarter valued at approximately $149,611,000. Finally, Capital World Investors purchased a new stake in Guidewire Software during the 4th quarter valued at $202,405,000.

Key Stories Impacting 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

Guidewire Software Company Profile

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.