Insider Selling: Guidewire Software (NYSE:GWRE) CEO Sells $152,400.00 in Stock

Guidewire Software, Inc. (NYSE:GWRE) CEO Michael George Rosenbaum sold 1,200 shares of the stock in a transaction on Tuesday, February 17th. The stock was sold at an average price of $127.00, for a total transaction of $152,400.00. Following the completion of the sale, the chief executive officer directly owned 230,743 shares of the company’s stock, valued at $29,304,361. The trade was a 0.52% decrease in their position. The transaction was disclosed in a filing with the Securities & Exchange Commission, which is accessible through this link.

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

• On Monday, February 2nd, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were 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 shares were sold at an average price of $160.32, for a total value 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 value of $187,512.00.
• On Tuesday, January 13th, Michael George Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $180.87, for a total value 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 value of $286,930.00.
• On Monday, December 22nd, Michael George Rosenbaum sold 1,400 shares of Guidewire Software stock. The shares were sold at an average price of $200.72, for a total value of $281,008.00.
• On Tuesday, December 16th, Michael George Rosenbaum sold 6,015 shares of Guidewire Software stock. The stock was sold at an average price of $192.08, for a total value of $1,155,361.20.
• On Monday, December 15th, Michael George Rosenbaum sold 1,400 shares of Guidewire Software stock. The stock was sold at an average price of $204.34, for a total value of $286,076.00.
• On Monday, December 8th, Michael George Rosenbaum sold 1,400 shares of Guidewire Software stock. The shares were sold at an average price of $210.87, for a total transaction of $295,218.00.
• On Monday, December 1st, Michael George Rosenbaum sold 1,400 shares of Guidewire Software stock. The stock was sold at an average price of $213.44, for a total transaction of $298,816.00.

Guidewire Software Price Performance

Shares of GWRE stock opened at $128.73 on Friday. The firm has a fifty day simple moving average of $167.22 and a 200-day simple moving average of $206.33. The company has a market capitalization of $10.94 billion, a PE ratio of 122.60, a price-to-earnings-growth ratio of 8.30 and a beta of 1.06. Guidewire Software, Inc. has a twelve month low of $120.37 and a twelve month high of $272.60. The company has a current ratio of 3.48, a quick ratio of 3.48 and a debt-to-equity ratio of 0.44.

Guidewire Software (NYSE:GWRE) last released its quarterly earnings results on Wednesday, December 3rd. The technology company reported $0.66 earnings per share (EPS) for the quarter, hitting the consensus estimate of $0.66. The firm had revenue of $332.64 million for the quarter, compared to the consensus estimate of $316.62 million. Guidewire Software had a net margin of 7.23% and a return on equity of 10.15%. The firm’s quarterly revenue was up 26.5% on a year-over-year basis. During the same quarter in the previous year, the firm posted $0.43 EPS. Equities research analysts anticipate that Guidewire Software, Inc. will post 0.52 earnings per share for the current fiscal year.

Guidewire Software declared that its Board of Directors has approved a share repurchase plan on Thursday, January 8th that allows the company to repurchase $500.00 million in shares. This repurchase authorization allows the technology company to reacquire up to 3.1% of its shares through open market purchases. Shares repurchase plans are usually a sign that the company’s board believes its stock is undervalued.

Wall Street Analysts Forecast Growth

A number of analysts have recently weighed in on the stock. Citizens Jmp reissued a “market outperform” rating and set a $281.00 price target on shares of Guidewire Software in a research report on Wednesday, December 10th. Weiss Ratings reiterated a “hold (c)” rating on shares of Guidewire Software in a research note on Thursday, January 22nd. Zacks Research downgraded shares of Guidewire Software from a “strong-buy” rating to a “hold” rating in a research report on Tuesday, December 2nd. DA Davidson upgraded shares of Guidewire Software from a “neutral” rating to a “buy” rating and upped their target price for the company from $246.00 to $250.00 in a research note on Wednesday, December 17th. Finally, Wall Street Zen downgraded Guidewire Software from a “buy” rating to a “hold” rating in a research note on Friday, November 28th. Eleven equities research analysts have rated the stock with a Buy rating, four have assigned a Hold rating and one has given a Sell rating to the company. According to MarketBeat, the stock presently has an average rating of “Moderate Buy” and an average price target of $259.77.

Key Headlines Impacting Guidewire Software

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

• Positive Sentiment: Sompo Group signed a long-term agreement to adopt Guidewire Cloud, a meaningful enterprise customer win that expands Guidewire’s global footprint and recurring cloud revenue visibility. Sompo Group and Guidewire Enter Long-Term Agreement
• Positive Sentiment: Guidewire released the London Market Tech Barometer showing brokers favor digitally advanced insurers — evidence that demand for Guidewire’s digital/cloud capabilities remains strong in key commercial insurance markets. London Market Tech Barometer
• Positive Sentiment: Unusual options activity—large call buying (1,297 calls, ~1,563% above average)—suggests some traders are positioned for upside into near-term news or catalysts. (Trade alert reported in market feeds.)
• Positive Sentiment: Guidewire has a $500M share repurchase authorization (announced earlier), which supports buy-side demand and signals management confidence in long-term value. (Referenced in recent MarketBeat coverage.)
• Neutral Sentiment: The company scheduled its Q2 FY2026 earnings release for March 5 (audio webcast), creating a near-term catalyst that can swing sentiment depending on guidance and execution. Earnings Release Announcement
• Neutral Sentiment: Market commentary and explainers (e.g., “Does Sompo’s New Cloud Deal Sharpen Guidewire’s Edge?”) are helping investors parse the Sompo deal’s strategic value versus valuation — useful context but not an immediate price driver. Does Sompo’s New Cloud Deal Sharpen Guidewire’s Edge?
• Negative Sentiment: BTIG cut its price target from $225 to $175 (still a “buy”), signaling some analyst concern on near-term valuation and adding downward pressure. BTIG Research Price Target Cut
• Negative Sentiment: CEO Michael Rosenbaum sold 1,200 shares (and has been selling periodically), which can weigh on sentiment even if sales are small relative to total holdings. SEC filing available for review. SEC Form 4 – Insider Sale

Institutional Inflows and Outflows

Several hedge funds and other institutional investors have recently modified their holdings of GWRE. IFP Advisors Inc raised its stake in Guidewire Software by 4.6% during the third quarter. IFP Advisors Inc now owns 1,104 shares of the technology company’s stock worth $254,000 after acquiring an additional 49 shares during the period. Earned Wealth Advisors LLC raised its position in shares of Guidewire Software by 5.4% during the 3rd quarter. Earned Wealth Advisors LLC now owns 989 shares of the technology company’s stock worth $227,000 after purchasing an additional 51 shares during the period. Smartleaf Asset Management LLC raised its position in shares of Guidewire Software by 9.3% during the 3rd quarter. Smartleaf Asset Management LLC now owns 624 shares of the technology company’s stock worth $145,000 after purchasing an additional 53 shares during the period. PDS Planning Inc lifted its holdings in shares of Guidewire Software by 6.4% in the 3rd quarter. PDS Planning Inc now owns 911 shares of the technology company’s stock worth $209,000 after purchasing an additional 55 shares during the last quarter. Finally, American Trust boosted its position in Guidewire Software by 3.9% during the 3rd quarter. American Trust now owns 1,632 shares of the technology company’s stock valued at $375,000 after purchasing an additional 61 shares during the period.

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.