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

June 3, 2026 by InsiderTrades.com

Key Points

Guidewire CEO Michael George Rosenbaum sold 1,200 shares on June 1 at an average price of $158.92, totaling $190,704. The sale was disclosed in an SEC filing and executed under a pre-arranged Rule 10b5-1 trading plan.
The CEO has been steadily selling shares in recent weeks, including multiple 1,200-share sales and one larger 4,737-share sale in March. After the latest transaction, he still directly owned 208,006 shares valued at about $33.1 million.
Guidewire remains well-followed by analysts and institutions, with a “Moderate Buy” consensus and an average price target of $244.46. The company also beat last quarter’s earnings and revenue estimates, while investors watch upcoming results and a recent $500 million share repurchase authorization.

Guidewire Software, Inc. (NYSE:GWRE - Get Free Report) CEO Michael George Rosenbaum sold 1,200 shares of the 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 directly owned 208,006 shares of the company's stock, valued at $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 through the SEC website. The transaction was executed under a pre-arranged Rule 10b5-1 trading plan.

Guidewire’s Buyback Could Be the Clue the Sell-Off Is Ending

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 5.2%

NYSE:GWRE opened at $162.51 on Wednesday. Guidewire Software, Inc. has a 52 week low of $115.57 and a 52 week high of $272.60. The firm has a 50 day moving average of $140.20 and a 200 day moving average of $162.43. 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 capitalization of $13.76 billion, a price-to-earnings ratio of 73.87 and a beta of 0.93.

Down 20%+, These 3 Software Stocks Are Boosting Buybacks

Guidewire Software (NYSE:GWRE - Get Free Report) last posted its earnings results on Thursday, March 5th. The technology company reported $1.17 EPS for the quarter, beating analysts' consensus estimates of $0.77 by $0.40. Guidewire Software had a net margin of 14.11% and a return on equity of 13.44%. The company had revenue of $359.10 million during the quarter, compared to analysts' expectations of $342.88 million. During the same quarter in the prior year, the company posted $0.51 earnings per share. Guidewire Software's revenue for the quarter was up 24.0% compared to the same quarter last year. As a group, 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 research analysts have issued reports on the stock. BTIG Research restated a "buy" rating and set a $200.00 price target on shares of Guidewire Software in a research note on Tuesday. Stifel Nicolaus lowered their price target on Guidewire Software from $300.00 to $250.00 and set a "buy" rating for the company in a research report on Friday, March 6th. Oppenheimer dropped their price target on Guidewire Software from $250.00 to $180.00 and set an "outperform" rating on the stock in a research note on Monday, May 18th. Zacks Research cut Guidewire Software from a "strong-buy" rating to a "hold" rating in a research note on Monday, May 25th. Finally, DA Davidson restated a "buy" rating and issued a $246.00 price objective on shares of Guidewire Software in a research note on Tuesday. Eleven analysts have rated the stock with a Buy rating, four have issued a Hold rating and one has assigned a Sell rating to the company. According to data from MarketBeat.com, Guidewire Software presently has an average rating of "Moderate Buy" and an average price target of $244.46.

AI Is Powering Guidewire Software’s Growth—So What Spooked the Market?

Read Our Latest Research Report on GWRE

Institutional Trading of Guidewire Software

A number of hedge funds and other institutional investors have recently made changes to their positions in GWRE. Advisors Asset Management Inc. acquired a new stake in shares of Guidewire Software in the first quarter worth $25,000. Amundi increased its stake in shares of Guidewire Software by 703.0% in the second quarter. Amundi now owns 36,093 shares of the technology company's stock worth $8,220,000 after acquiring an additional 31,598 shares during the period. Jump Financial LLC acquired a new stake in shares of Guidewire Software in the second quarter worth $305,000. Bank of Nova Scotia increased its stake in shares of Guidewire Software by 30.9% in the second quarter. Bank of Nova Scotia now owns 2,024 shares of the technology company's stock worth $477,000 after acquiring an additional 478 shares during the period. Finally, NewEdge Advisors LLC increased its stake in shares of Guidewire Software by 30.6% in the second quarter. NewEdge Advisors LLC now owns 4,911 shares of the technology company's stock worth $1,156,000 after acquiring an additional 1,152 shares during the period.

More Guidewire Software News

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

Positive Sentiment: BTIG Research reaffirmed its Buy rating on Guidewire Software and kept a $200 price target, implying upside from current levels. BTIG Reaffirms Buy on Guidewire Software
Positive Sentiment: DA Davidson also reiterated a Buy rating and raised its target to $246, signaling expectations for continued execution and meaningful long-term upside. DA Davidson Reaffirms Buy on Guidewire Software
Positive Sentiment: Investors are positioning ahead of Guidewire’s upcoming Q3 FY2026 earnings, with analysts watching cloud subscription momentum, annual recurring revenue (ARR), and margins as key catalysts. Guidewire to Report Q3 Earnings: Here's What Investors Should Know
Positive Sentiment: Recent news also highlights a $500 million share repurchase authorization, which can support the stock by signaling confidence in cash generation and capital allocation. Guidewire Software jumps as focus turns to upcoming Q3 results and capital return
Neutral Sentiment: Guidewire is expected to report revenue of roughly $352 million to $358 million, so the market is likely focused on whether the company can beat expectations and maintain cloud growth momentum. Guidewire Software Q3 Earnings on the Horizon
Negative Sentiment: A recent market commentary noted that GWRE shares fell after a strong prior-day gain, suggesting some traders may be taking profits or reducing exposure before earnings. Guidewire Software Inc Shares Fall 5.1%

Guidewire Software Company Profile

(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.