Guidewire Software Inc SEC Filings

Director Michael C. Keller of Guidewire Software (GWRE) executed two significant stock sales over consecutive days:

• On June 24, 2025: Sold 1,000 shares at $237.525 per share
• On June 25, 2025: Sold another 1,000 shares at $239.00 per share

Following these transactions, Keller's direct ownership stands at 9,410 shares. The sales were executed through his attorney-in-fact, Winston King. These transactions represent a reduction in Keller's direct holdings but maintain his position as a company director. The sequential sales at increasing prices suggest favorable market conditions for GWRE stock during this period.

Form 144 Notice of Proposed Sale filed for Guidewire Software (NYSE: GWRE) indicates an insider's intent to sell securities. The filing details a proposed sale of 1,000 shares of Class A Common Stock with an aggregate market value of $239,000 through UBS Financial Services, planned for June 25, 2025.

Key transaction details:

• Original acquisition: 2,000 shares through open market purchase on June 15, 2022
• Recent insider sales by Michael C Keller in the past 3 months: - 860 shares on June 16, 2025 ($218,836) - 1,000 shares on June 24, 2025 ($237,419)
• Current shares outstanding: 84,195,000

This Form 144 represents a routine insider sale declaration, required when affiliates intend to sell securities. The seller confirms no knowledge of undisclosed material adverse information regarding Guidewire's operations.

Guidewire Software, Inc. (GWRE) – Form 144 Notice of Proposed Sale

An individual affiliate intends to sell 1,000 Class A common shares through UBS Financial Services on or about 24 June 2025. The shares are valued at an aggregate $238,000, implying an average reference value of roughly $238 per share. Compared with the company’s 84.195 million shares outstanding, the planned sale represents only 0.0012 % of the float, indicating no material dilution or change in control.

The filer previously acquired 2,000 shares in an open-market cash purchase on 15 June 2022. During the past three months, the same insider—identified as Michael C. Keller—sold 860 shares on 16 June 2025, generating $218,836 in gross proceeds (≈ $254 per share). All representations affirm the seller is unaware of undisclosed adverse information, in accordance with Rule 144 and Rule 10b5-1 requirements.

Because the transaction size is immaterial relative to GWRE’s market capitalization and share count, the filing is largely administrative. Nevertheless, it signals incremental insider liquidity activity investors may monitor for trend development.

Guidewire Software CEO Michael George Rosenbaum reported the sale of 1,400 shares of common stock at a price of $238.12 per share on June 23, 2025. The transaction was executed as part of a pre-planned 10b5-1 trading plan established on October 15, 2024.

Following the transaction, Rosenbaum continues to hold 237,268 shares directly. The sale represents a small portion of his total holdings, approximately 0.6% of his position. The transaction was automatically executed under the trading plan, which helps executives avoid accusations of insider trading by establishing predetermined trading parameters.

Key Transaction Details:

• Transaction Type: Automatic sale under 10b5-1 plan
• Total Transaction Value: Approximately $333,368
• Position: CEO and Director
• Ownership Form: Direct

Guidewire Software, Inc. (GWRE) has filed a Form 144, indicating the intended sale of 1,585 common shares with an aggregate market value of $395,380.31. The planned trade is scheduled for 18 June 2025 through Morgan Stanley Smith Barney on the NYSE. The filing also discloses that the same insider—identified in prior sales data as Jeffrey Cooper—has sold 4,933 shares for total proceeds of $1.11 million over the last three months (2,826 shares on 17 June 2025 and 2,107 shares on 19 March 2025).

The proposed sale represents less than 0.002 % of GWRE’s outstanding 84.2 million shares, suggesting limited dilution or market-supply impact. No relationship to the issuer or additional adverse information was provided, and the filer affirmed that no undisclosed material information is known. While insider sales can sometimes be viewed negatively, the relatively small size versus float keeps the market impact minimal.

Guidewire Software CEO Michael George Rosenbaum reported two significant stock transactions:

• On June 16, 2025, executed an automatic sale of 1,400 shares at $254.53 per share through a pre-established 10b5-1 Trading Plan from October 2024
• On June 17, 2025, disposed of 5,925 shares at an average price of $248.94 to cover tax obligations related to Restricted Stock Unit settlement

Following these transactions, Rosenbaum directly owns 238,668 shares of Guidewire Software (GWRE). The sales were executed through standard insider trading compliance procedures, with the first transaction following an automated trading plan and the second addressing tax obligations. These transactions represent routine executive stock management rather than strategic investment decisions.

James Winston King, Chief Administrative Officer and General Counsel of Guidewire Software (GWRE), reported a significant insider transaction on June 17, 2025. The executive disposed of 1,230 shares at an average price of $248.9384 per share.

The transaction was executed as a tax-related sale, where shares were sold by the issuer to cover tax obligations associated with the settlement of Restricted Stock Units (RSUs). Following the transaction, King retains beneficial ownership of 39,923 shares held directly.

The sale prices ranged from $248.9379 to $248.9388 per share. This transaction appears to be a routine tax withholding event rather than a discretionary sale by the insider, suggesting it may not signal any particular view on the company's valuation or prospects.