Insider Selling: Guidewire Software (NYSE:GWRE) CEO Sells $192,000.00 in Stock

Guidewire Software, Inc. (NYSE:GWRE) CEO Michael George Rosenbaum sold 1,200 shares of the business’s stock in a transaction on Monday, March 16th. The shares were sold at an average price of $160.00, for a total value of $192,000.00. Following the transaction, the chief executive officer owned 225,943 shares of the company’s stock, valued at approximately $36,150,880. The trade was a 0.53% decrease in their position. The transaction was disclosed in a document filed with the Securities & Exchange Commission, which is available through this hyperlink.

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

• On Tuesday, March 17th, Michael George Rosenbaum sold 4,737 shares of Guidewire Software stock. The stock was sold at an average price of $163.86, for a total value of $776,204.82.
• On Monday, March 9th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $166.34, for a total value of $199,608.00.
• On Monday, February 23rd, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $125.50, for a total value of $150,600.00.
• On Tuesday, February 17th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $127.00, for a total transaction of $152,400.00.
• On Monday, February 2nd, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $140.01, for a total transaction of $168,012.00.
• On Monday, January 26th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $160.32, for a total transaction of $192,384.00.
• On Tuesday, January 20th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $156.26, for a total transaction of $187,512.00.
• On Tuesday, January 13th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $180.87, for a total transaction of $217,044.00.
• On Monday, December 29th, Michael George Rosenbaum sold 1,400 shares of Guidewire Software stock. The shares were sold at an average price of $204.95, for a total transaction of $286,930.00.
• On Monday, December 22nd, Michael George Rosenbaum sold 1,400 shares of Guidewire Software stock. The stock was sold at an average price of $200.72, for a total transaction of $281,008.00.

Guidewire Software Stock Performance

Guidewire Software stock opened at $156.00 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. The company has a market capitalization of $13.21 billion, a PE ratio of 70.91, a P/E/G ratio of 7.22 and a beta of 1.06. The company has a 50 day moving average price of $148.72 and a 200-day moving average price of $197.49. Guidewire Software, Inc. has a fifty-two week low of $120.37 and a fifty-two week high of $272.60.

Guidewire Software (NYSE:GWRE) last released its quarterly earnings data on Thursday, March 5th. The technology company reported $1.17 EPS for the quarter, topping the consensus estimate of $0.77 by $0.40. Guidewire Software had a return on equity of 13.44% and a net margin of 14.11%.The company had revenue of $359.10 million for the quarter, compared to the consensus estimate of $342.88 million. During the same period last year, the business posted $0.51 EPS. Guidewire Software’s quarterly revenue was up 24.0% on a year-over-year basis. As a group, equities analysts forecast that Guidewire Software, Inc. will post 0.52 earnings per share for the current year.

Guidewire Software declared that its Board of Directors has approved a stock repurchase plan on Thursday, January 8th that permits the company to buyback $500.00 million in outstanding shares. This buyback authorization permits the technology company to reacquire up to 3.1% of its stock through open market purchases. Stock buyback plans are typically an indication that the company’s management believes its stock is undervalued.

More Guidewire Software News

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

• Positive Sentiment: Large call‑option flow — traders bought ~1,297 GWRE call contracts (≈1,563% above average), signaling speculative positioning for upside in the near term.
• Positive Sentiment: Board buyback — a $500M repurchase authorization (~3.1% of shares) remains a structural support and signal management sees value in the equity. Guidewire Buyback Article
• Positive Sentiment: Recent fundamentals are strong — Q4 revenue and EPS beat (March 5) and continued analyst bullishness (consensus “Moderate Buy”, average target near $250) provide longer‑term upside support. MarketBeat GWRE Coverage
• Neutral Sentiment: Strategic narrative shifting — coverage highlights AI tailwinds and modernization opportunities for P&C insurers; these are positives over time but not an immediate catalyst.
• Neutral Sentiment: Technical/contextual note — 50‑day moving average sits well below the 200‑day average, and intraday volume has been below recent averages, which can amplify directional moves until volume confirms a trend change.
• Negative Sentiment: Concentrated insider selling — multiple senior executives (CEO Michael Rosenbaum, President John Mullen, CFO Jeffrey Cooper, CAO David Peterson and others) executed clustered sales totalling several hundred to thousands of shares in the $160–$164 area; that kind of clustered insider trimming can sap investor confidence and trigger near‑term selling pressure. InsiderTrades: CEO Sells

Institutional Inflows and Outflows

Several hedge funds have recently added to or reduced their stakes in GWRE. Rockefeller Capital Management L.P. increased its holdings in shares of Guidewire Software by 59.3% during the fourth quarter. Rockefeller Capital Management L.P. now owns 13,709 shares of the technology company’s stock valued at $2,756,000 after acquiring an additional 5,104 shares in the last quarter. DUTCH ASSET Corp acquired a new stake in Guidewire Software in the 4th quarter worth approximately $570,000. Corient Private Wealth LLC boosted its stake in Guidewire Software by 36.9% in the 4th quarter. Corient Private Wealth LLC now owns 10,820 shares of the technology company’s stock worth $2,177,000 after purchasing an additional 2,915 shares in the last quarter. Caitong International Asset Management Co. Ltd grew its position in Guidewire Software by 471.3% during the 4th quarter. Caitong International Asset Management Co. Ltd now owns 497 shares of the technology company’s stock worth $100,000 after purchasing an additional 410 shares during the last quarter. Finally, MidFirst Bank acquired a new position in Guidewire Software during the 4th quarter valued at approximately $212,000.

Analyst Upgrades and Downgrades

Several research analysts have issued reports on GWRE shares. DA Davidson reiterated a “buy” rating and set a $246.00 target price on shares of Guidewire Software in a report on Tuesday, March 10th. Zacks Research upgraded shares of Guidewire Software from a “hold” rating to a “strong-buy” rating in a report on Friday, March 13th. Citizens Jmp reaffirmed a “market outperform” rating and issued a $281.00 price target on shares of Guidewire Software in a research report on Wednesday, December 10th. Oppenheimer dropped their price objective on shares of Guidewire Software from $300.00 to $250.00 and set an “outperform” rating on the stock in a research note on Tuesday, February 24th. Finally, Stifel Nicolaus cut their price objective 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. One research analyst has rated the stock with a Strong Buy rating, eleven have given a Buy rating, three have given a Hold rating and one has assigned a Sell rating to the company’s stock. According to MarketBeat, the stock currently has a consensus rating of “Moderate Buy” and a consensus target price of $249.85.

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.