Insider Selling: Guidewire Software (NYSE:GWRE) CFO Sells $3,356,615.98 in Stock

Guidewire Software, Inc. (NYSE:GWRE) CFO Jeffrey Cooper sold 23,234 shares of the company’s stock in a transaction on Thursday, September 17th. The shares were sold at an average price of $144.47, for a total transaction of $3,356,615.98. Following the completion of the transaction, the chief financial officer owned 95,361 shares of the company’s stock, valued at $13,776,803.67. This represents a 19.59% decrease in their position. The transaction was disclosed in a filing with the Securities & Exchange Commission, which is available 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.

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

• On Friday, September 18th, Jeffrey Cooper sold 9,941 shares of Guidewire Software stock. The stock was sold at an average price of $142.61, for a total value of $1,417,686.01.

Guidewire Software Stock Up 1.8%

GWRE opened at $153.10 on Thursday. Guidewire Software, Inc. has a one year low of $102.30 and a one year high of $255.89. 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 stock has a market capitalization of $12.75 billion, a P/E ratio of 93.93 and a beta of 0.97. The business’s 50-day simple moving average is $164.69 and its 200-day simple moving average is $147.40.

Guidewire Software (NYSE:GWRE) last released its quarterly earnings results on Thursday, September 3rd. The technology company reported $0.99 earnings per share (EPS) for the quarter, topping 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 firm had revenue of $411.09 million for the quarter, compared to the consensus estimate of $402.61 million. During the same quarter last year, the business posted $0.84 EPS. The firm’s quarterly revenue was up 15.3% compared to the same quarter last year. Analysts anticipate that Guidewire Software, Inc. will post 2.46 EPS for the current year.

Analyst Upgrades and Downgrades

Several analysts recently commented on the stock. Weiss Ratings reiterated a “hold (c)” rating on shares of Guidewire Software in a research report on Monday, August 31st. Needham & Company LLC reissued a “hold” rating on shares of Guidewire Software in a research report on Friday, September 4th. Robert W. Baird lifted their price objective on shares of Guidewire Software from $202.00 to $235.00 and gave the company an “outperform” rating in a research note on Monday, August 31st. Wells Fargo & Company lifted their price objective on shares of Guidewire Software from $190.00 to $195.00 and gave the company an “overweight” rating in a research note on Friday, September 4th. Finally, 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 report on Friday, September 4th. Twelve equities research analysts have rated the stock with a Buy rating and four have assigned a Hold rating to the company’s stock. According to MarketBeat, the company currently has an average rating of “Moderate Buy” and a consensus target price of $216.23.

Guidewire Software News Summary

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

Institutional Inflows and Outflows

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

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.