Guidewire Software CEO Files Form 144 for $10.4M Automatic Sell-to-Cover

Executive Summary

On September 17, 2026, Guidewire Software, Inc. (NYSE: GWRE) Chief Executive Officer Michael George Rosenbaum filed a Form 144 notice disclosing the intended sale of 72,290 shares of common stock with an aggregate market value of approximately $10.44 million.

Transaction Details

• Proposed Sale Date: September 17, 2026
• Shares to be Sold: 72,290 shares (~0.09% of 81,992,669 shares outstanding)
• Estimated Aggregate Market Value: $10,443,866.46 (~$144.47 per share)
• Broker: Morgan Stanley Smith Barney LLC Executive Financial Services
• Source of Shares: Vesting of multiple RSU and PSU grants on September 15, 2026, totaling 134,149 shares acquired as equity compensation.

Strategic Context & Nature of Sale

As explicitly stated in the filing remarks, this planned disposition consists strictly of automatic sell-to-cover transactions required to satisfy statutory tax withholding liabilities arising from the vesting of RSUs and performance-based PSUs under Guidewire's Amended and Restated 2020 Stock Plan. Because the sale is non-discretionary and routine, it carries Low trading significance and does not signal negative executive sentiment or a change in insider conviction.