Insider Selling: Guidewire Software (NYSE:GWRE) CEO Sells $153,828.00 in Stock

Posted by Amy Steele on May 21st, 2026

Guidewire Software, Inc. (NYSE:GWRE – Get Free Report) CEO Michael George Rosenbaum sold 1,200 shares of the firm’s stock in a transaction that occurred on Monday, May 18th. The stock was sold at an average price of $128.19, for a total value of $153,828.00. Following the sale, the chief executive officer directly owned 210,406 shares of the company’s stock, valued at $26,971,945.14. This represents a 0.57% decrease in their position. The transaction was disclosed in a document filed with the Securities & Exchange Commission, which can be accessed through this hyperlink. 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 11th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was 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 stock was 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 stock was sold at an average price of $138.09, for a total transaction of $165,708.00.
On Monday, April 20th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $139.75, for a total transaction of $167,700.00.
On Monday, April 13th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $118.77, for a total transaction of $142,524.00.
On Monday, April 6th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $151.14, for a total transaction of $181,368.00.
On Monday, March 23rd, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $155.56, for a total transaction of $186,672.00.
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 transaction 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.
On Monday, March 9th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $166.34, for a total value of $199,608.00.

Guidewire Software Price Performance

Shares of GWRE opened at $139.82 on Thursday. The business’s fifty day moving average is $142.62 and its 200 day moving average is $166.80. Guidewire Software, Inc. has a 12-month low of $115.57 and a 12-month high of $272.60. The company has a quick ratio of 2.93, a current ratio of 2.93 and a debt-to-equity ratio of 0.45. The stock has a market cap of $11.84 billion, a P/E ratio of 63.55 and a beta of 0.91.

Guidewire Software (NYSE:GWRE – Get Free Report) last released its quarterly earnings data on Thursday, March 5th. The technology company reported $1.17 earnings per share for the quarter, topping the consensus estimate of $0.77 by $0.40. The firm had revenue of $359.10 million for the quarter, compared to the consensus estimate of $342.88 million. Guidewire Software had a net margin of 14.11% and a return on equity of 13.44%. The business’s revenue was up 24.0% on a year-over-year basis. During the same quarter in the prior year, the company posted $0.51 earnings per share. Sell-side analysts anticipate that Guidewire Software, Inc. will post 1.84 earnings per share for the current fiscal year.

Analyst Upgrades and Downgrades

A number of brokerages have recently issued reports on GWRE. DA Davidson reiterated a “buy” rating and set a $246.00 price objective on shares of Guidewire Software in a report on Tuesday, March 10th. Wells Fargo & Company dropped their target price on Guidewire Software from $250.00 to $210.00 and set an “overweight” rating on the stock in a report on Wednesday, February 4th. Oppenheimer dropped their target price on Guidewire Software from $250.00 to $180.00 and set an “outperform” rating on the stock in a report on Monday. BTIG Research raised their target price on Guidewire Software from $175.00 to $200.00 and gave the company a “buy” rating in a report on Friday, March 6th. Finally, Zacks Research upgraded Guidewire Software from a “hold” rating to a “strong-buy” rating in a report on Friday, March 13th. One research analyst has rated the stock with a Strong Buy rating, eleven have assigned a Buy rating, three have given a Hold rating and one has assigned a Sell rating to the stock. According to MarketBeat, Guidewire Software presently has an average rating of “Moderate Buy” and a consensus target price of $244.46.

Get Our Latest Analysis on GWRE

Institutional Inflows and Outflows

A number of large investors have recently made changes to their positions in the company. IFP Advisors Inc lifted its position in shares of Guidewire Software by 4.6% during the third quarter. IFP Advisors Inc now owns 1,104 shares of the technology company’s stock valued at $254,000 after purchasing an additional 49 shares in the last quarter. Smartleaf Asset Management LLC lifted its holdings in Guidewire Software by 9.3% during the third quarter. Smartleaf Asset Management LLC now owns 624 shares of the technology company’s stock worth $145,000 after acquiring an additional 53 shares during the period. American Trust lifted its holdings in Guidewire Software by 3.9% during the third quarter. American Trust now owns 1,632 shares of the technology company’s stock worth $375,000 after acquiring an additional 61 shares during the period. Arkadios Wealth Advisors lifted its holdings in Guidewire Software by 1.7% during the third quarter. Arkadios Wealth Advisors now owns 3,739 shares of the technology company’s stock worth $859,000 after acquiring an additional 62 shares during the period. Finally, Parkside Financial Bank & Trust lifted its holdings in Guidewire Software by 7.5% during the third quarter. Parkside Financial Bank & Trust now owns 963 shares of the technology company’s stock worth $221,000 after acquiring an additional 67 shares during the period.

About Guidewire Software

(Get Free Report)

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.