Form 4: Guidewire Software CEO Sells Shares Under Pre-Arranged Plan and for Tax Obligations

Guidewire Software, Inc. CEO Michael George Rosenbaum reported the sale of common stock totaling 7,325 shares through a pre-arranged trading plan and to cover tax liabilities from Restricted Stock Unit settlements.

Summary

• Michael George Rosenbaum, CEO and Director of Guidewire Software, Inc. (GWRE), reported two separate sales of common stock.
• On June 16, 2025, Mr. Rosenbaum sold 1,400 shares of common stock at a price of $254.53 per share.
• This sale was an automatic transaction executed pursuant to a Rule 10b5-1 Trading Plan, which was adopted on October 15, 2024.
• Following this transaction, Mr. Rosenbaum's direct beneficial ownership stood at 244,593 shares.
• On June 17, 2025, an additional 5,925 shares of common stock were sold at an average price of $248.938 per share (ranging from $248.9377 to $248.9386).
• This second sale was conducted by the Issuer (Guidewire Software, Inc.) to cover tax obligations associated with the settlement of Mr. Rosenbaum's Restricted Stock Units.
• After both reported transactions, Mr. Rosenbaum's direct beneficial ownership of Guidewire Software common stock is 238,668 shares.

Sentiment

Score: 6

Explanation: The sentiment is neutral to slightly positive. While insider sales reduce ownership, these specific sales are non-discretionary (pre-planned 10b5-1) or for tax purposes (RSU settlement), which are routine and do not typically signal a lack of confidence in the company's future performance. The transparency of the 10b5-1 plan adoption date adds to the neutrality.

Negatives

• The CEO sold a total of 7,325 shares of company stock, which reduces his direct ownership stake.

Future Outlook

This Form 4 filing does not contain any forward-looking statements or guidance regarding the company's future performance or outlook.

Industry Context

This filing is a routine disclosure of insider stock transactions and does not provide information directly related to broader industry trends or competitive landscape. Such sales, particularly those under 10b5-1 plans or for tax purposes, are common among executives in the software industry and generally do not signal a change in company fundamentals.

Stakeholder Impact

• Shareholders: The sale of shares by the CEO slightly dilutes his direct ownership, but given the non-discretionary nature of the sales, it is unlikely to be interpreted as a negative signal regarding the company's prospects. It's a routine part of executive compensation and financial planning.

Key Dates

Keywords

Guidewire Software, GWRE, Michael George Rosenbaum, CEO, Director, Insider Trading, Stock Sale, Form 4, 10b5-1 Plan, Restricted Stock Units, Tax Obligations