Insider Selling: Guidewire Software (NYSE:GWRE) CEO Sells $224,628.00 in Stock

Guidewire Software, Inc. (NYSE:GWRE) CEO Michael Rosenbaum sold 1,200 shares of Guidewire Software stock in a transaction dated Monday, October 26th. The shares were sold at an average price of $187.19, for a total value of $224,628.00. Following the transaction, the chief executive officer directly owned 273,666 shares in the company, valued at approximately $51,227,538.54. This trade represents a 0.44% decrease in their position. The transaction was disclosed in a filing with the Securities & Exchange Commission, which is accessible through the SEC website. The transaction was executed under a pre-arranged Rule 10b5-1 trading plan.

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

• On Monday, October 19th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $167.90, for a total value of $201,480.00.
• On Monday, October 12th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $168.97, for a total transaction of $202,764.00.
• On Monday, October 5th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $152.52, for a total transaction of $183,024.00.
• On Monday, September 28th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $142.65, for a total transaction of $171,180.00.
• 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 Thursday, September 17th, Michael Rosenbaum sold 72,290 shares of Guidewire Software stock. The shares were sold at an average price of $144.47, for a total transaction 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.

Guidewire Software Trading Down 1.3%

Shares of NYSE:GWRE opened at $166.92 on Thursday. The firm has a fifty day moving average of $167.82 and a two-hundred day moving average of $149.56. The firm has a market capitalization of $13.90 billion, a P/E ratio of 102.41 and a beta of 1.02. Guidewire Software, Inc. has a 12-month low of $102.30 and a 12-month high of $253.79. The company has a quick ratio of 1.79, a current ratio of 1.79 and a debt-to-equity ratio of 0.57.

Guidewire Software (NYSE:GWRE) last posted its quarterly earnings results on Thursday, September 3rd. The technology company reported $0.99 EPS for the quarter, beating the consensus estimate of $0.93 by $0.06. Guidewire Software had a net margin of 9.44% and a return on equity of 12.66%. The business had revenue of $411.09 million for the quarter, compared to analysts’ expectations of $402.61 million. During the same period in the previous year, the company posted $0.84 EPS. Guidewire Software’s revenue was up 15.3% on a year-over-year basis. On average, equities analysts expect that Guidewire Software, Inc. will post 2.45 EPS for the current fiscal year.

Key Headlines Impacting Guidewire Software

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

• Positive Sentiment: Guidewire agreed to acquire UK-based Hyperexponential for approximately $1.7 billion upfront, with additional payments of up to $400 million. The transaction would add AI-powered pricing, risk modeling, and underwriting capabilities to Guidewire’s insurance software platform, potentially strengthening its competitive position. Guidewire To Acquire Hyperexponential
• Positive Sentiment: The company launched an “agentic insurance” platform that combines applications, data, workflows, and governance controls to help insurers deploy AI across product development, underwriting, pricing, and claims. Management is positioning the initiative as a way to move customers from experimental AI projects to broader production use. Guidewire Delivers the Open, Secure, and Complete Core Platform for Agentic Insurance
• Neutral Sentiment: Guidewire’s analyst and investor-day presentations, along with the merger call, focused on the strategic rationale for Hyperexponential and the company’s AI roadmap. Investors still need more clarity on financing, integration, timing, and the acquisition’s effect on revenue growth, margins, and earnings. Guidewire M&A Call Transcript
• Negative Sentiment: The acquisition represents a substantial capital commitment for Guidewire, raising concerns about dilution, near-term profitability, integration risk, and whether the expected AI benefits will justify the purchase price. Those concerns are amplified by GWRE’s premium valuation, with a price-to-earnings ratio above 100.
• Negative Sentiment: CEO Michael Rosenbaum sold 1,200 shares for approximately $224,628, and President John Mullen sold 1,800 shares for approximately $336,942. Both sales were executed under pre-arranged Rule 10b5-1 plans and represented small portions of their remaining holdings, limiting their significance but creating a modest negative sentiment signal. Guidewire President Sells Shares

Institutional Inflows and Outflows

A number of institutional investors have recently made changes to their positions in the stock. State of Wyoming grew its stake in Guidewire Software by 23.0% in the 3rd quarter. State of Wyoming now owns 1,896 shares of the technology company’s stock valued at $270,000 after buying an additional 355 shares during the last quarter. D.A. Davidson & CO. raised its holdings in Guidewire Software by 3.9% in the 3rd quarter. D.A. Davidson & CO. now owns 4,418 shares of the technology company’s stock worth $630,000 after acquiring an additional 164 shares during the period. Angeles Wealth Management LLC lifted its position in Guidewire Software by 2.5% during the 3rd quarter. Angeles Wealth Management LLC now owns 2,831 shares of the technology company’s stock worth $404,000 after acquiring an additional 70 shares during the last quarter. Oppenheimer & Co. Inc. acquired a new position in Guidewire Software during the 3rd quarter worth $229,000. Finally, Signaturefd LLC lifted its position in Guidewire Software by 1.4% during the 3rd quarter. Signaturefd LLC now owns 5,324 shares of the technology company’s stock worth $759,000 after acquiring an additional 72 shares during the last quarter.

Analyst Upgrades and Downgrades

Several research analysts have weighed in on the company. Oppenheimer upped their target price on Guidewire Software from $200.00 to $210.00 and gave the stock an “outperform” rating in a research report on Friday, September 4th. Weiss Ratings reiterated a “hold (c)” rating on shares of Guidewire Software in a report on Monday, August 31st. Wells Fargo & Company boosted their price target on Guidewire Software from $190.00 to $195.00 and gave the company an “overweight” rating in a research note on Friday, September 4th. Piper Sandler restated an “overweight” rating and issued a $210.00 price objective on shares of Guidewire Software in a report on Friday, September 4th. Finally, Guggenheim increased their price objective on Guidewire Software from $180.00 to $210.00 and gave the stock a “buy” rating in a report on Thursday, August 27th. Twelve investment analysts have rated the stock with a Buy rating and four have issued a Hold rating to the company. Based on data from MarketBeat.com, Guidewire Software presently has an average rating of “Moderate Buy” and an average price target of $216.23.

Guidewire Software Company Profile

Guidewire Software, Inc provides cloud-based software designed for the property and casualty insurance industry. Its platform helps insurers manage core operations, including policy administration, billing, claims management, underwriting, and digital customer engagement.

The company’s principal offerings include InsuranceSuite, which incorporates PolicyCenter, BillingCenter, and ClaimCenter, as well as products for insurance data management, analytics, digital experiences, and application development.