Insider Selling: Guidewire Software (NYSE:GWRE) CFO Sells $1,417,686.01 in Stock

Guidewire Software, Inc. (NYSE:GWRE) CFO Jeffrey Cooper sold 9,941 shares of the firm’s stock in a transaction dated Friday, September 18th. The shares were sold at an average price of $142.61, for a total transaction of $1,417,686.01. Following the sale, the chief financial officer owned 85,420 shares of the company’s stock, valued at approximately $12,181,746.20. This represents a 10.42% decrease in their ownership of the stock. The transaction was disclosed in a filing with the SEC, which is available through 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.

Jeffrey Elliott Cooper also recently made the following trade(s):

• On Thursday, September 17th, Jeffrey Cooper sold 23,234 shares of Guidewire Software stock. The shares were sold at an average price of $144.47, for a total transaction of $3,356,615.98.

Guidewire Software Price Performance

Shares of GWRE opened at $153.10 on Thursday. The company has a market capitalization of $12.75 billion, a P/E ratio of 93.93 and a beta of 0.97. 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 50 day moving average of $164.69 and a 200 day moving average of $147.40. Guidewire Software, Inc. has a twelve month low of $102.30 and a twelve month high of $255.89.

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

Institutional Trading of Guidewire Software

Several large investors have recently modified their holdings of GWRE. Bamco Inc. NY purchased a new stake in Guidewire Software during the second quarter valued at $1,106,768,000. Linonia Partnership LP purchased a new position in Guidewire Software in the second quarter worth about $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 bought a new stake in shares of Guidewire Software during the 2nd quarter valued at about $149,611,000. Finally, Capital World Investors bought a new stake in shares of Guidewire Software during the 4th quarter valued at about $202,405,000.

Analysts Set New Price Targets

Several equities research analysts recently commented on GWRE shares. The Goldman Sachs Group dropped their price objective on Guidewire Software from $255.00 to $225.00 and set a “buy” rating on the stock in a research report on Friday, June 5th. Royal Bank Of Canada restated an “outperform” rating and set a $215.00 target price on shares of Guidewire Software in a research note on Friday, September 4th. Stifel Nicolaus dropped 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. Guggenheim lifted their price target on shares of Guidewire Software from $180.00 to $210.00 and gave the stock a “buy” rating in a research note on Thursday, August 27th. Finally, Robert W. Baird boosted their price objective on shares of Guidewire Software from $202.00 to $235.00 and gave the company an “outperform” rating in a report on Monday, August 31st. Twelve research analysts have rated the stock with a Buy rating and four have given a Hold rating to the stock. According to data from MarketBeat, Guidewire Software has an average rating of “Moderate Buy” and a consensus price target of $216.23.

More Guidewire Software News

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.