Insider Selling: Guidewire Software (NYSE:GWRE) CEO Sells $190,704.00 in Stock

Posted by Brian Himes on Jun 5th, 2026

Guidewire Software, Inc. (NYSE:GWRE – Get Free Report) CEO Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock in a transaction that occurred on Monday, June 1st. The shares were sold at an average price of $158.92, for a total transaction of $190,704.00. Following the sale, the chief executive officer owned 208,006 shares in the company, valued at approximately $33,056,313.52. The trade was a 0.57% decrease in their position. The transaction was disclosed in a legal filing with the Securities & Exchange Commission, 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 Tuesday, May 26th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $138.51, for a total transaction of $166,212.00.
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 transaction 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 transaction 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 transaction 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 transaction 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 transaction 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 transaction 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 transaction 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 transaction 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 transaction of $776,204.82.

Guidewire Software Trading Down 2.4%

Guidewire Software stock opened at $151.27 on Friday. The stock has a market cap of $12.81 billion, a P/E ratio of 68.76 and a beta of 0.93. The company has a debt-to-equity ratio of 0.45, a current ratio of 2.93 and a quick 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’s 50 day moving average price is $140.32 and its 200-day moving average price is $161.08.

Guidewire Software (NYSE:GWRE – Get Free Report) last announced its quarterly earnings results on Thursday, June 4th. The technology company reported $0.82 earnings per share for the quarter, topping the consensus estimate of $0.79 by $0.03. Guidewire Software had a net margin of 14.11% and a return on equity of 13.44%. The company had revenue of $372.54 million for the quarter, compared to analysts’ expectations of $355.92 million. During the same quarter in the previous year, the business posted $0.88 earnings per share. Guidewire Software’s quarterly revenue was up 26.9% 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.

Trending Headlines about Guidewire Software

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

Positive Sentiment: Guidewire Software beat Q3 expectations, reporting $0.82 EPS versus the $0.79 consensus and $372.5 million in revenue versus $355.9 million expected, showing continued demand for its insurance software platform.
Positive Sentiment: The company also guided Q4 revenue to $396 million-$406 million and full-year revenue to about $1.5 billion, which came in above Street estimates and suggests healthy momentum into year-end.
Positive Sentiment: Management said the quarter reinforced confidence in the business and pointed to a potentially record fourth quarter, which may support longer-term investor sentiment.
Neutral Sentiment: Analysts remain broadly constructive, with recent reiterations of Buy ratings from firms including BTIG and DA Davidson, but the stock had already rallied ahead of earnings, limiting immediate upside reaction.
Neutral Sentiment: Recent insider selling by CEO Michael George Rosenbaum was disclosed under a pre-arranged trading plan, which is not usually a major fundamental concern but can add modest headline pressure.
Negative Sentiment: Despite the beat-and-raise style report, the stock fell as investors likely locked in gains after a strong run and focused on whether Guidewire can sustain cloud growth and margin expansion from here.

Analysts Set New Price Targets

Several equities research analysts recently weighed in on GWRE shares. Stifel Nicolaus reduced their price target on shares of Guidewire Software from $300.00 to $250.00 and set a “buy” rating on the stock in a research report on Friday, March 6th. Oppenheimer reduced their price target on shares of Guidewire Software from $250.00 to $180.00 and set an “outperform” rating on the stock in a research report on Monday, May 18th. Zacks Research cut shares of Guidewire Software from a “strong-buy” rating to a “hold” rating in a research report on Monday, May 25th. DA Davidson restated a “buy” rating and issued a $246.00 price target on shares of Guidewire Software in a research report on Tuesday. Finally, BTIG Research restated a “buy” rating and issued a $200.00 price target on shares of Guidewire Software in a research report on Tuesday. Eleven equities research analysts have rated the stock with a Buy rating and three have given a Hold rating to the stock. According to MarketBeat.com, the stock has a consensus rating of “Moderate Buy” and a consensus price target of $251.50.

Get Our Latest Report on Guidewire Software

Institutional Inflows and Outflows

Institutional investors and hedge funds have recently bought and sold shares of the company. Advisors Asset Management Inc. purchased a new position in Guidewire Software during the first quarter worth $25,000. Measured Wealth Private Client Group LLC purchased a new position in Guidewire Software during the third quarter worth $29,000. Cornerstone Planning Group LLC boosted its stake in Guidewire Software by 620.0% during the third quarter. Cornerstone Planning Group LLC now owns 144 shares of the technology company’s stock worth $34,000 after buying an additional 124 shares during the period. Hazlett Burt & Watson Inc. purchased a new position in Guidewire Software during the third quarter worth $35,000. Finally, Flagship Harbor Advisors LLC purchased a new position in Guidewire Software during the fourth quarter worth $36,000.

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.