Insider Selling: Guidewire Software (NYSE:GWRE) CEO Sells $166,212.00 in Stock

Guidewire Software, Inc. (NYSE:GWRE) CEO Michael George Rosenbaum sold 1,200 shares of the stock in a transaction dated Tuesday, May 26th. The shares were sold at an average price of $138.51, for a total value of $166,212.00. Following the completion of the sale, the chief executive officer owned 209,206 shares of the company’s stock, valued at approximately $28,977,123.06. This trade represents a 0.57% decrease in their position. The transaction was disclosed in a filing with the SEC, which is available at 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, May 18th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $128.19, for a total value of $153,828.00.
• On Monday, May 11th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $136.38, for a total value of $163,656.00.
• On Monday, May 4th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $141.91, for a total value of $170,292.00.
• On Monday, April 27th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $138.09, for a total value of $165,708.00.
• On Monday, April 20th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $139.75, for a total value of $167,700.00.
• On Monday, April 13th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $118.77, for a total value of $142,524.00.
• On Monday, April 6th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $151.14, for a total value of $181,368.00.
• On Monday, March 23rd, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $155.56, for a total value of $186,672.00.
• On Tuesday, March 17th, Michael George Rosenbaum sold 4,737 shares of Guidewire Software stock. The shares were sold at an average price of $163.86, for a total value of $776,204.82.
• On Monday, March 16th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $160.00, for a total value of $192,000.00.

Guidewire Software Price Performance

GWRE stock opened at $142.49 on Friday. The company has a debt-to-equity ratio of 0.45, a quick ratio of 2.93 and a current ratio of 2.93. Guidewire Software, Inc. has a 1 year low of $115.57 and a 1 year high of $272.60. The firm has a market cap of $12.06 billion, a P/E ratio of 64.77 and a beta of 0.91. The stock has a 50-day simple moving average of $140.02 and a 200-day simple moving average of $163.22.

Guidewire Software (NYSE:GWRE) last issued its quarterly earnings data on Thursday, March 5th. The technology company reported $1.17 earnings per share for the quarter, beating analysts’ consensus estimates of $0.77 by $0.40. Guidewire Software had a return on equity of 13.44% and a net margin of 14.11%.The firm had revenue of $359.10 million during the quarter, compared to analyst estimates of $342.88 million. During the same quarter last year, the firm earned $0.51 EPS. Guidewire Software’s quarterly revenue was up 24.0% on a year-over-year basis. On average, equities analysts predict that Guidewire Software, Inc. will post 1.84 earnings per share for the current fiscal year.

More Guidewire Software News

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

• Positive Sentiment: Zacks Research nudged up its earnings outlook for FY2026, FY2027, Q2 2027, and Q1 2028, signaling slightly better profitability expectations for Guidewire Software. Guidewire Software earnings estimate updates
• Positive Sentiment: The company’s latest reported quarter beat expectations, with EPS of $1.17 versus $0.77 expected and revenue of $359.1 million topping estimates, reinforcing momentum in its cloud software business. Guidewire Software earnings beat
• Neutral Sentiment: Guidewire’s analyst backdrop remains constructive overall, with a Moderate Buy consensus and an average target price above the current trading range, but Zacks still rates the stock Hold. Guidewire Software analyst ratings
• Negative Sentiment: CEO Michael George Rosenbaum sold 1,200 shares in a pre-arranged transaction, adding to recent insider sales and creating a mild headwind for sentiment. Guidewire CEO stock sale
• Negative Sentiment: Zacks also trimmed some near-term estimates, including Q3 2026 and Q4 2027 EPS, which may be limiting upside despite the broader optimism. Guidewire Software estimate revisions

Institutional Inflows and Outflows

A number of large investors have recently bought and sold shares of GWRE. Capital World Investors bought a new position in Guidewire Software during the 4th quarter worth approximately $202,405,000. Principal Financial Group Inc. lifted its holdings in Guidewire Software by 547.3% during the 1st quarter. Principal Financial Group Inc. now owns 1,180,334 shares of the technology company’s stock worth $176,537,000 after buying an additional 997,992 shares during the last quarter. Alliancebernstein L.P. lifted its holdings in Guidewire Software by 405.1% during the 2nd quarter. Alliancebernstein L.P. now owns 538,303 shares of the technology company’s stock worth $126,743,000 after buying an additional 431,725 shares during the last quarter. Stockbridge Partners LLC lifted its holdings in Guidewire Software by 39.0% during the 4th quarter. Stockbridge Partners LLC now owns 1,445,206 shares of the technology company’s stock worth $290,501,000 after buying an additional 405,850 shares during the last quarter. Finally, Assenagon Asset Management S.A. lifted its holdings in Guidewire Software by 179.0% during the 1st quarter. Assenagon Asset Management S.A. now owns 628,759 shares of the technology company’s stock worth $94,037,000 after buying an additional 403,370 shares during the last quarter.

Wall Street Analyst Weigh In

Several analysts recently issued reports on GWRE shares. Zacks Research cut shares of Guidewire Software from a “strong-buy” rating to a “hold” rating in a report on Monday. Stifel Nicolaus cut their price target on shares of Guidewire Software from $300.00 to $250.00 and set a “buy” rating on the stock in a report on Friday, March 6th. BTIG Research upped their price target on shares of Guidewire Software from $175.00 to $200.00 and gave the company a “buy” rating in a report on Friday, March 6th. Wells Fargo & Company cut their price target on shares of Guidewire Software from $250.00 to $210.00 and set an “overweight” rating on the stock in a report on Wednesday, February 4th. Finally, Royal Bank Of Canada cut their price target on shares of Guidewire Software from $300.00 to $250.00 and set an “outperform” rating on the stock in a report on Friday, March 6th. Eleven analysts have rated the stock with a Buy rating, four have given a Hold rating and one has assigned a Sell rating to the company’s stock. According to MarketBeat.com, the stock currently has an average rating of “Moderate Buy” and an average price target of $244.46.

Guidewire Software Company Profile

Guidewire Software, Inc develops software products and cloud services for property and casualty (P&C) insurance carriers. Headquartered in San Mateo, California, the company’s offerings are designed to help insurers manage the core functions of their business—policy administration, billing and claims—while supporting digital engagement, analytics and operational modernization.

Guidewire’s core product portfolio is commonly known as the InsuranceSuite, which includes PolicyCenter for policy administration, BillingCenter for billing and receivables, and ClaimCenter for claims management.