Insider Selling: Guidewire Software (NYSE:GWRE) CEO Sells $171,180.00 in Stock

Key Points

• Guidewire CEO Michael Rosenbaum sold 1,200 shares for $171,180 at an average price of $142.65 under a pre-arranged Rule 10b5-1 plan. He retained 278,466 shares valued at approximately $39.7 million, while recent filings show a series of additional sales.
• Guidewire’s latest quarterly results exceeded expectations, with EPS of $0.99 versus the $0.93 consensus and revenue of $411.09 million, up 15.3% year over year.
• Analysts remain broadly positive, with a “Moderate Buy” consensus and an average price target of $216.23, although the stock’s high valuation and elevated expectations remain potential risks.

Guidewire Software, Inc. (NYSE:GWRE - Get Free Report) CEO Michael Rosenbaum sold 1,200 shares of the company's stock in a transaction that occurred on Monday, September 28th. The stock was sold at an average price of $142.65, for a total value of $171,180.00. Following the transaction, the chief executive officer directly owned 278,466 shares in the company, valued at $39,723,174.90. The trade was a 0.43% decrease in their ownership of the stock. The sale was disclosed in a document filed 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.

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

• On Monday, September 21st, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $145.92, for a total value of $175,104.00.
• On Thursday, September 17th, Michael Rosenbaum sold 72,290 shares of Guidewire Software stock. The shares were sold at an average price of $144.47, for a total transaction of $10,443,736.30.
• On Monday, September 14th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $145.87, for a total transaction of $175,044.00.
• On Tuesday, September 8th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $160.52, for a total transaction of $192,624.00.
• On Monday, August 31st, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $204.44, for a total transaction of $245,328.00.
• On Monday, August 24th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $187.82, for a total transaction of $225,384.00.
• On Monday, August 17th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $172.88, for a total transaction of $207,456.00.
• On Monday, August 10th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The stock was sold at an average price of $169.50, for a total transaction of $203,400.00.
• On Monday, August 3rd, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $155.92, for a total transaction of $187,104.00.
• On Monday, July 27th, Michael Rosenbaum sold 1,200 shares of Guidewire Software stock. The shares were sold at an average price of $142.31, for a total value of $170,772.00.

Guidewire Software Stock Up 0.3%

GWRE traded up $0.40 during midday trading on Wednesday, reaching $142.92. 1,097,685 shares of the company were exchanged, compared to its average volume of 1,575,000. The company has a market cap of $11.90 billion, a price-to-earnings ratio of 87.68 and a beta of 0.97. Guidewire Software, Inc. has a one year low of $102.30 and a one year high of $255.89. The company's fifty day moving average price is $164.56 and its 200 day moving average price is $146.94. The company has a debt-to-equity ratio of 0.57, a quick ratio of 1.79 and a current ratio of 1.79.

Guidewire Software (NYSE:GWRE - Get Free Report) last posted its earnings results on Thursday, September 3rd. The technology company reported $0.99 earnings per share for the quarter, beating analysts' consensus estimates of $0.93 by $0.06. Guidewire Software had a return on equity of 12.66% and a net margin of 9.44%.The company had revenue of $411.09 million for the quarter, compared to analyst estimates of $402.61 million. During the same quarter last year, the company earned $0.84 earnings per share. The company's revenue for the quarter was up 15.3% on a year-over-year basis. As a group, analysts expect that Guidewire Software, Inc. will post 2.45 EPS for the current year.

Key Guidewire Software News

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

• Positive Sentiment: Improved cash flow and buybacks support the stock. Guidewire exited fiscal 2026 with operating cash flow up 30% and repurchased $606 million of its shares, suggesting stronger profitability and operating leverage. Guidewire's Cash Flow and Buybacks: Can Both Keep Scaling?
• Positive Sentiment: West Bend is preparing for AI-enabled claims processing on Guidewire. The insurer’s implementation provides evidence that Guidewire’s platform could benefit from increasing demand for automation and artificial intelligence in insurance operations. West Bend Lays the Foundation for AI-Driven Claims on Guidewire
• Neutral Sentiment: Analyst estimates are mixed but imply longer-term earnings growth. Zacks Research raised several 2028 estimates, including fiscal 2028 EPS to $3.18 from $2.64 and projected fiscal 2029 EPS of $4.36. However, it lowered fiscal 2027 EPS to $1.98 from $2.06, reduced first-quarter 2027 EPS to $0.26 from $0.37, and cut second-quarter 2027 EPS to $0.44 from $0.55.
• Negative Sentiment: High expectations and valuation remain potential headwinds. Brown Capital Management said elevated expectations are weighing on Guidewire, particularly amid broader uncertainty surrounding AI spending and market volatility. The stock’s high earnings multiple and position below its 50-day moving average may make investors more sensitive to any execution or forecast shortfall. Elevated Expectations Weigh on Guidewire

Hedge Funds Weigh In On Guidewire Software

A number of hedge funds and other institutional investors have recently made changes to their positions in the stock. Fiduciary Financial Advisors purchased a new stake in Guidewire Software during the second quarter worth about $29,000. Leonteq Securities AG purchased a new position in Guidewire Software in the first quarter valued at about $36,000. Bogart Wealth LLC grew its position in shares of Guidewire Software by 127.8% during the 1st quarter. Bogart Wealth LLC now owns 246 shares of the technology company's stock valued at $37,000 after acquiring an additional 138 shares during the period. Harbour Investments Inc. grew its position in shares of Guidewire Software by 83.0% during the 4th quarter. Harbour Investments Inc. now owns 247 shares of the technology company's stock valued at $50,000 after acquiring an additional 112 shares during the period. Finally, Silvant Capital Management LLC purchased a new stake in shares of Guidewire Software during the 2nd quarter worth approximately $33,000.

Analyst Upgrades and Downgrades

Several analysts have recently issued reports on GWRE shares. Oppenheimer upped their target price on shares of Guidewire Software from $200.00 to $210.00 and gave the stock an "outperform" rating in a research note on Friday, September 4th. The Goldman Sachs Group cut their price target on shares of Guidewire Software from $255.00 to $225.00 and set a "buy" rating on the stock in a report on Friday, June 5th. Weiss Ratings reiterated a "hold (c)" rating on shares of Guidewire Software in a research note on Monday, August 31st. Guggenheim lifted their target price on shares of Guidewire Software from $180.00 to $210.00 and gave the stock a "buy" rating in a research report on Thursday, August 27th. Finally, BTIG Research boosted their target price on Guidewire Software from $175.00 to $230.00 and gave the stock a "buy" rating in a research note on Wednesday, September 2nd. Twelve equities research analysts have rated the stock with a Buy rating and four have given a Hold rating to the company. According to data from MarketBeat.com, the company presently has an average rating of "Moderate Buy" and a consensus target price of $216.23.

Guidewire Software Company Profile

Guidewire Software, Inc develops software for the property and casualty (P&C) insurance industry. Its platform is designed to help insurers manage core operations, modernize legacy systems, and support digital interactions with policyholders, agents, brokers, and other stakeholders.

The company's principal offerings include Guidewire InsuranceSuite, a cloud-based platform with applications such as PolicyCenter for policy administration, BillingCenter for billing and payments, and ClaimCenter for claims management.

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