Guidewire Software Inc SEC Filings

Jeffrey Elliott Cooper, Chief Financial Officer of Guidewire Software, Inc. (GWRE), received 21,194 performance shares on September 15, 2025 as a result of vested performance-based awards and plan mechanics, increasing his beneficial ownership to 98,749 shares. The award description notes earlier adjustments: 249 PSUs were added after FY23 performance and an additional 2,754 PSUs were credited after FY25 performance. On September 16, 2025 Cooper sold 14,103 shares to cover taxes related to RSU settlement at an average sale price of approximately $242.8668 per share, leaving him with 84,646 shares beneficially owned. The performance share award underlying the 21,194 shares is exercisable and converts into common stock and has an indicated expiration/action date of September 15, 2032.

Michael George Rosenbaum, CEO and a director of Guidewire Software, reported changes in his beneficial ownership following performance-share vesting and a sale to cover taxes. On 09/15/2025 the reporting person was issued 45,849 performance shares (PSUs) deemed earned and immediately vested as to Part 2, increasing his direct beneficial ownership to 295,275 shares. On 09/16/2025 he sold 30,317 shares at an average price of approximately $242.8659 per share to cover taxes, leaving 264,958 shares beneficially owned. The filing states the PSUs reflect above-target performance (including a prior 101.8% achievement for FY23 and 120% for FY25) and notes the sale was to satisfy tax withholding on RSU settlement.

Form 144 filed for Guidewire Software, Inc. (GWRE) reporting a proposed sale of common stock by an insider. The notice lists 30,317 shares to be sold through Morgan Stanley Smith Barney at an aggregate market value of $7,362,964.57, with an approximate sale date of 09/16/2025 on the NYSE. The securities were acquired as restricted stock units on 09/15/2025 as compensation and are being sold by Michael George Rosenbaum's account via Guidewire Software address. The filing also discloses prior insider sales in the past three months totaling 25,525 shares across multiple dates and transactions, with gross proceeds reported for each sale.

Form 144 notice relates to a proposed sale of 14,103 shares of Common Stock through Morgan Stanley Smith Barney LLC on the NYSE with an aggregate market value of $3,425,149.84. The securities were reported as acquired on 09/15/2025 as restricted stock units received as compensation and paid for on that date. The filing lists prior sales by the same person, Jeffrey Elliott Cooper, of 1,585 shares on 06/18/2025 for $395,380.31 and 2,826 shares on 06/17/2025 for $703,498.81. Several issuer identification fields in the filing are blank in the provided content.

Form 144 filed for Guidewire Software, Inc. (GWRE) shows a proposed sale of 15,869 shares of common stock to be executed through Morgan Stanley Smith Barney on 09/16/2025 with an aggregate market value of $3,854,054.08. The shares were acquired 09/15/2025 as compensation in the form of restricted stock units and were reported as paid on 09/15/2025. The filer, John P. Mullen, also reported four prior sales in the past three months totaling 21,141 shares that generated gross proceeds of $3,297,522.31. The notice includes the filer’s representation that they are unaware of undisclosed material adverse information about the issuer.

Guidewire Software (GWRE) Form 144 shows proposed sale of 7,149 shares of Common Stock through Morgan Stanley Smith Barney LLC on or about 09/16/2025. The filing reports an aggregate market value of $1,736,256.28 for those shares and lists total shares outstanding of 84,530,578. The shares were acquired as restricted stock units on 09/15/2025 as compensation and were recorded as acquired and paid on that date. The filer, identified as James Winston King, also disclosed sales totaling 4,511 shares in the prior three months with gross proceeds of $1,022,923.95. The notice includes the standard representation that the seller has no undisclosed material information.

Form 144 notice for Guidewire Software, Inc. (GWRE) reports a proposed sale of 1,811 shares of common stock through Morgan Stanley Smith Barney LLC on 09/16/2025 with an aggregate market value of $439,833.05. The filing shows these shares were acquired one day earlier on 09/15/2025 as restricted stock units (compensation) and that no securities were sold by the reporting person in the past three months. The issuer outstanding shares figure is reported as 84,530,578. Several filer contact fields and the specific reporting person name are not populated in the provided content.

Michael George Rosenbaum, CEO and Director of Guidewire Software (GWRE), reported insider transactions. On 09/11/2025 he was credited with 28,958 shares tied to Performance Shares at a reported price of $0, bringing his beneficial ownership to 250,826 shares. The filing notes these Performance Shares are subject to a three-year performance period with continued employment through September 15, 2028.

On 09/15/2025 an automatic sale under a 10b5-1 trading plan executed the disposition of 1,400 shares at $252.83, reducing his beneficial ownership to 249,426. The sale was reported by an attorney-in-fact on behalf of Rosenbaum.

Guidewire Software (GWRE) insider James Winston King received a grant of performance-based equity. On 09/11/2025 Mr. King was awarded 5,687 performance shares that will convert into 5,687 shares of common stock if performance and continued employment conditions are met. The awards cliff vest based on the average results of three one-year performance periods and require continued employment through September 15, 2028. The grant reports $0 as the conversion/exercise price and shows Mr. King beneficially owning 42,329 shares following the transaction. The Form 4 is signed 09/15/2025.